On baseball caps – and logos in general

Monday, September 18th 2023
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Baseball caps are, in many ways, the lazy option for headwear. They’re ubiquitous, they’re cheap and they go with everything. I completely understand those that fight the good fight for brimmed hats, and feel it necessary to attack ball caps in the process. 

But a baseball cap can have an elegance to it, even with smarter clothing and tailoring. There are also good ones and bad ones, and people they suit more or less. So it’s likely worth writing some bits on PS - starting today with a personal piece on logos.

A baseball cap worn with fine clothing appeals (of course) because of the contrast. Here's a piece of sportswear being worn with something that is certainly not sportswear. One’s fine and sharp, the other (ideally) worn and battered. It’s a species of high/low dressing - which is always easiest with outerwear and accessories. 

Though hasn’t this look been done to death? Haven’t Drake’s and related preppy brands, before them and since, made it trite? This is a question every reader has to answer for themselves, because it’s heavily dependent on their environs, their milieu

Just keep in mind that you don’t live online. Despite the apparent prevalence of that style, I have yet to see a single person wearing it where I live in my little pocket of south London, and hardly anyone in Mayfair. Beware the perspective-distorting effects of the echo chamber. 

There are levels of quality to a baseball cap, but as long as it’s 100% cotton (or leather, or wool - not a synthetic) it’s hard to go wrong. Even the little plastic adjustor on the back has some retro appeal, though personally I prefer cotton or leather. 

However, I do think a cap is better with a logo, something personal.

A logo seems to look better to me because of the cap’s sportswear origins, and the fact so many of those have a prominent device. Without it, a baseball cap (not a military cap, or anything of that ilk) feels lacking. 

A useful example is the growth of ‘luxury’ caps in recent years, particularly those that became a subject of discussion around the ‘stealth wealth’ of Succession

To me, those caps, often from Loro Piana, feel rather lifeless. Like they’ve had the character and style sucked out of them. In the same way as cashmere denim, it's the result of someone trying to make a luxury version and removing its essence in the process. 

My antipathy towards that type of cap is about the luxury material as well as the lack of logo, but they both feel symptomatic of the same neutered approach.  

As to what a logo could be, my answer is anything meaningful. 

You wear a band T-shirt to proclaim your passion for that band; you wear a football top to declare your loyalty to the team. I feel like a cap should be similar.

Mine tend to be souvenirs or brands I’m happy to represent. Ralph Lauren, Rubato, a red one from Holiday Boileau that reminds me of a nice day with the team in Paris - and which feels particularly significant given the shop no longer exists, and the whole 16th scene seems to be fading. 

My favourite of course is my ‘Cal’ cap, from Berkeley in the US. I didn’t go, but it was a gift from a friend that did, so that feels OK. It still feels authentic. 


It shouldn’t be a surprise that given all this, I’m not a big fan of the ironic logo, of a made-up club or team. 

Wouldn’t it be cooler to actually wear the name of your local gardening club, where you volunteer on Sundays? Or the local tennis club? Perhaps the issue is people aren't members of such clubs any more.

Last June we took these shots in the Circolo del Tennis in Florence, which is the most wonderful place - old school style, baize tables and newspapers on sticks, kids running around in their white kit on the blazing clay courts. 

The following week I was on Chiltern Street in London, and the back half of a shop had been taken over by an imagined tennis club, the Rochambeau. The idea was to promote a particular rosé wine - Racquet - that otherwise didn’t have a back story like other French wines. 

It was all very clever, very well done - but it was really just another type of hype. After Florence, it felt a little hollow. 

The one cap I have without a logo is from RRL which seems different because the rough-out suede is so rugged: it’s a whole outer layer on its own. Waxed caps feel similar. 

Other exceptions include recreations of military caps that would never have had something on them, and of course actual vintage models. 

Thinking about it, what I really want to push against is the prevalence of plain caps worn as just another piece of practical headwear, like a beanie (below). And perhaps the artificial distressed ones, which look so artificial. Just wear them and if you absolutely need to, sticking them in the washing machine a couple of times.

As with many rants, I’ve started with a feeling and rationalised my way through it. It’s cathartic. Hopefully some useful points rubbed off along the way.

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I’ve been wanting you to write an article on this topic for some time, so thanks! And a pleasant surprise when I thought we’d had our 3 pieces for the week.


I think the look in the “how to dress like milad abedi” where he’s wearing the polo sport cap is a great illustration of how to wear a cap well.

Rowan Morrison

An unexpected plot twist!
Was expecting this to be in favour of the no-logo cap.
I wear a plain cap, often with a smart outfit, simply because I don’t like wearing things with logos.
I totally get the appeal of something with logos on that have personal value though. My most stylish friend also avoids logos except for a worn old hoodie with the logo of the little village cricket team he plays for in his spare time. I’ve often thought it’s funny (and saying a lot about the concept of style) that he makes it look so cool, even when he’s wearing it among people who would have no idea that it’s his team or indeed even have heard of the team.
It’s not logos, but the only graphic or printed t-shirts I wear are souvenir t-shirts from places I’ve been. Countries, cities or theme parks. I don’t know if it’s stylish but it’s just a habit I enjoy and feels right as part of my “personal uniform”.
Great article, thanks!

Peter Hall

I’m always quite disappointed that traditionalcricket caps (for UK readers) are not worn more -they can be smart.

My son mentions that Japanese baseball caps are uber cool.


Yes! Enjoyed the article and vehemently agree with this point. I like a baseball cap; my personal preference is the classic baseball teams, it is after all where they come from and the iconography is quite unique, but it is a shame cricket has adopted them whilst somewhat abandoning it’s own traditions and style.
Cricket’s sartorial decline is something of a personal crusade, I have to admit, but It’s not just the headgear, either. The famous whites are almost all now just ill fitting polo shirts. And I don’t think there has ever been a good coloured kit, certainly nothing like the classic football kits. Compared to old photos of cricketers with rolled up sleeves and full button shirts, looking elegant and dashing, it’s a disappointing look.
I keep hoping someone else picks up the baton on this as well, but that’s perhaps for somewhere else.

john kalell

We’ll articulated, Jonathan.


i wouldn’t say its lazy. There are so many variations of a cap and i have searched high and low to find one that’s just right for me. Its similar with denim. People assume that because its so ubiquitous that’s it a lazy option when often finding an items that’s just right is allot harder than say a tailored jacket. Id also caution against over analysing these things. I know men are somewhat neurotic with respect to style and clothing and love to be ‘thoughtful etc’ but this can go to far.


The point about logos really resonates with me. Logos that are from your company, a sports club or a society you are a member of then it’s a nice touch even (especially?) if the majority of people would not recognise it.

Lindsay McKee

There’s nothing that gets my heckles up more than someone wearing a baseball cap in reverse, peak facing backwards.
It looks terrible.
Let’s take an example and I can speak as an ex-security man Simon!!!
If I worked as a security man in a shopping mall or a department store or a door man in a nice shop, and someone came along wearing a baseball cap in reverse, I would have given them more than a passing glance…put it that way. Same with a hoodie which I detest also.
That said, I have worn my Jack Wolfskin, properly, with pride in the city or on holiday, no probs….never reversed!
Keep em conservative…not too loud.
We have seen certain US presidents wear baseball caps. No problem.
Baseball caps are great…in their proper place!!
Garish logos on clothing is not for me.
Logos on tee shirts and the like are fine as long as it’s a worthy cause and offends no-one.
End of rant !!!

Eric Michel

Logo/No Logo, Proper/Reverse… everything depends on your age and how you dress. My son is 20 and has been wearing a reverse cap all summer, and it was pretty cool. I would clearly not do it at my age, but if you are young enough and your style is on the cooler side, why not.

Tommy Mack

Did the trend of wearing your cap backwards come simply from farm labourers, mechanics etc working outdoors protecting the back of their necks from the sun? I’ve always assumed so and that it became fashionable because of the rugged blue collar associations (and then amplified by the explosion of hip hop and its street/sportswear fashions)

What was really daft was the fashion about 15 years ago for young lads wearing a golf visor not only back to front but upside down too, like a miniature rain hopper for the back of your head!


I think it came from Ken Griffey – at least he popularized it. His dad played in the majors when he was young and his dad would always put a hat on him, but his head wasnt big enough and the brim would block his view. So they would put it on him backwards. And he popularized the look in his young days in baseball, “The Kid” was the coolest thing in baseball and pretty damn good.


I don’t mind a logo free cap, but I think it definitely needs some texture or other visual interest to compensate for that and keep it casual. Something like a slubby linen or a herringbone with some colour elevates it above being just another uneventful luxury cap.
It also helps if the materials used are more suited to warmer weather, since that leans into the hats practical nature. I remember seeing a woman wearing a logo free cap made out of a loosely woven pale straw, which looked very good given how hot that day was.


I bought a ready-made herringbone fine linen cap without a logo made by a local bespoke hatmaker, and I like wearing it with jackets as it’s less formal than brimmed hats like panamas but still not too casual.

andrew hughes

I have a linen baseball cap from Lock & Co without the logo

Peter Smith Wright

Sorry Simon, but I think the notion of wearing a baseball cap with tailoring is a bit too much for my taste.


For what it worths I totally agree. I highly admire the job Simon does here but I see this as a surrendering to current times, when everyone think everything is allowed, times when a man I know was fiercely claiming, a month ago, he didn’t wear a shirt since he was twenty, and he is 70 yo now! Nothing personal Simon, you do a fantastic job here, but I see a baseball cap worn over a db coat as silly. Just it.

john kalell

And , may I add, we have an ex president here who routinely wears logo-ed baseball caps. And bright, shiny blue, Iill-fitting suits which distract, possibly, from the foolishness of his choices in headwear.
Has there ever been a less stylish , more inappropriate public figure ?

john kalell

Where I live the baseball cap is so derivative (here baseball is a sport), so overworked, and so trite that it’s impossible to take seriously a guy who wears one with tailoring.
Trying much too hard for my liking.

jarrod williams

Completely disagree. I find it odd that you single out the baseball cap for being overworked and incongruous with tailoring but not other athletic classics such as the sweatshirt, rugby or even shooting jacket. American Ivy League style, which combines easy tailoring with sporting pieces, has been copied the world over and the baseball cap is a fixture in that style category.


I look at dad caps the same way I view jewelry, if it’s personal it works.


I completely understand those that fight the good fight for brimmed hats, and feel it necessary to attack ball caps in the process.” I am probably of “those” that you are referring to. A brimmed hat, trilby or fedora, provides valuable ear protection in very hot, sunny, wet or cold weather.

I have felt, tweed, cotton calico, Panama straw and linen trilbies that were made by Olney (a corporate lockdown victim) in Luton. Failsworth (which supplies lots of country, menswear and department stores) offers much better value than Bates, Lock or Christy’s in St James’s whose prices have rocketed over the last couple of years.


Since the sunny weather returned, I’ve been wearing Olney cotton trilbies of varying weights and linings. Lock sells the Monaco, almost identical to the last one I bought (possibly Olney NOS), for a whopping £175!

Why don’t you try one of Anderson & Sheppard’s cotton trilbies? They are made in Italy, priced at a reasonable £125 and available in black, navy or ivory to an add a touch of class to your favourite summer outfits. Go on, I dare you! 🙂


Personally I only wear when weather appropriate. I prefer either no brand, one which is not instantly recognisable or simply a bit different., your Holiday one being a good example. As for style i like your one but not the style worn by Brian Cox in the picture. Perhaps they a called something different?
One point: a civilian must never ever, ever wear one backwards, that is a golden rule.


Great points.and completely agree. Thanks for explaining.
What is essentially a functional piece and should be treated has such, has been hijacked. The main re beaten up the better as far as I’m concerned.


Great musings as always. I think caps-with-logos is illustrative of present menswear fashion, where vintage and workwear are worn in their original make. Say, 10 years ago, I remember buying clothes taking cues from vintage or workwear, but making them slim or a bit more minimal. Perhaps “elevated” or “contemporary” were the marketing terms. Real vintage or workwear felt too loose or boxy back then.
I completely agree on the fake team logos, it feels like children’s clothing.
Also illustrating the point on logos: The RRL suede cap actually does have a logo at the front panel 🙂

Caveat Emptor

As someone who generally avoids logos, I second the idea of one on a baseball cap. To me they provide a personal connection with a place I have lived (NY), attended university (Cal Berkeley!) or simply enjoy (their Satanic Majesties).


Hey Simon, great article.
Did you see that there are Cashmere caps by Luca Faloni? Though expensive they are pretty nice.


I’m not a logo person by and large but I agree – baseball caps often seem empty without anything on them. I currently just have a needlecord cap from Drake’s with a Mughal archer on it – which feels somewhat appropriate as a history graduate. Otherwise, the only club I belong to doesn’t do baseball caps. I considered one with a small logo from RL but I don’t have anything else from them, which makes it feel a bit inauthentic for me personally. A fake logo badminton club one from Drake’s appealed to me because I used to play badminton, albeit not anymore.


Hi Simon,
Just a quick of off subject comment. I would strongly recommend the newly opened ‘Gabrielle Chanel. Fashion Manifesto’ the Victoria and Albert Museum in London.
You have mentioned about the business side of fashion in articles. What I learnt from this exhibition was that she neatly embodies; an extremely high level of creativity, superb networking and marketing, and a generally very astute business sense. All at a time when women were breaking of the older traditional. I doubt I would have personally liked her and there are questions about her wartime behaviours, something we have touched on historically. .
I only mentioned the exhibition as it covers an excellent example of how to succeed in the fashion business.


True enough. Whilst the designs were great to look at, the descriptions of her path to success is where I found the real value- perhaps that too is in the accompanying book that we purchased. Exit through the gift shop!


I’m not saying I’d never wear a logo cap but I’m not quite there yet. To me it’s a bit too unnatural with tailoring, a bit too loud. A bit too tell and not show.

While I think it’s not elegant, I can appreciate the contrast. It might make you more approachable and also make you more at ease to approach others as you will feel more relaxed. It works in the right context and occasion.


I love my RL Wimbledon Caps. Not the basic ones, the ones they every single tournament in a new design. They’re hilariously expensive, but well worth it if you love tennis (as I do). They feel special if you’ve been to Wimbledon that year and bought one of the caps as a souvenir (as I did in 2019!)
Have a nice week everyone!


Another good example Clint played by Robert Shaw in Jaws, for nailing the look in 1975!


I think you mean Quint

Lindsay McKee

Logos on the outside of leathergoods is a no no.
Like tailoring , logos need to be very discreet and hidden.
Ideally no logos at all unless absolutely necessary!


Hi Simon, how do you factor in the age of the wearer? Weirdly, I always thought that worn-in baseball caps looked better on older guys.


I’m very much of the opinion that baseball caps should only be worn by Americans and the under-20s.. They’re not waterproof, they add very little warmth. Their only function, and their only saving grace, is to shield the eyes and the scalp from bright sunlight. A Panama is a far better option for this.


Sadly Thorh I can assure you that when you have very little hair a basic shield between the elements and the top of your head does make a difference in rain and when it is cold.


What distinguishes high/low dressing from mismatches? For me a baseball cap with an Ulster coat is a mismatch, for you it seems to be high/low dressing. But what about a double breasted suit with Air Jordans? Is it purely subjective?


A good subject this. As a European transplanted (permanently) to the US for over 25 years, I have a particular distaste for caps though I certainly wear them myself occasionally when it’s sunny. They are pervasive in the US, from coast-to-coast, worn indoors and out. And they are worn year round in restaurants or on the street at night, when there is no need for shade nor for something to keep your head warm. This behaviour creates a very dull and boring streetscape lacking in any imagination. Especially since outside of the large metropolitan areas the caps are almost always the cheapest you can buy. Thankfully in most of Europe they are nowhere near as pervasive, especially indoors. It’s a delight to see that, though sadly that’s changing fast – even in places less apt to ape America.


I love the idea of taking one off inside, but I find that my “hat hair” looks far worse than wearing the cap.

Chris S

‘worn year round in restaurants’ Except if Tony Soprano’s at the next table… https://www.youtube.com/watch?v=Hqp1bGuiHHs


I do not really see the difference between a logo on a baseballcap or on a polo or t-shirt. I like neither.


As a lifelong cap wearer I am certainly in the pro camp on this issue. But of course, as with all matters relating to style, its a personal matter. The whole cap and check jacket combos look awesome in photo shoots but I must admit to struggling with wearing the look myself – I just don’t feel natural and so tend to stick to casual wear. I often find my most prized caps are quite cheap, and come from the most unlikely of places but for readers who are keen for a quality baseball cap, I highly recommend Ebbets Field Flannels. Very well-made baseball caps, from USA. Some models are made of very soft flannel, and come with a brush to maintain, others are made of cotton. Logo’s are of baseball and other sports teams from past and present and across the globe. I have the fortune of regularly travelling to the USA, however they do occasionally come up in the UK on sites like Marrkt or ebay for those who wish to avoid the cost of postage and duty.


Interesting, I hope that was anomalous and not a sign of changes in quality. The last time I bought something new from them was about two years ago: one cotton and one flannel. They are both great with the minor complaint that the clasp for the leather strap on one is a bit too prone to coming undone. The fabric was good in my opinion and I haven’t had the issues you mention.

Peter Hall

Ebbets caps have definitely dropped in quality. My son(mentioned above) used to regularly buy Japanese baseball caps and he now buys directly from Japan. He thinks it is a post covid cost measure.

However,the vintage MLB caps still seem to be of decent quality-prices have increased inevitably.


This might be what you’re referring to, but they were purchased by Lids last November. I don’t have a post-acquisition cap (yet) to compare against, but they now do a lot more “our bestsellers but in a new seasonal colorway” like the big corporations do for MLB teams. It would be easier to imagine trading quality for more quantity, but it also means I’ve finally got a cap from my favorite NPL team in the mail, so who’s to say?


How about waxed baseball caps?


A topic that highly interests me, because I’ve been looking for a way out from wearing baseball caps, to be honest. I need some form of daily headwear for protection against sunlight, as I’m practically bald and any degree of sunburn might trigger a, let’s say, nasty condition.
So I’ve tried:
– flat caps in tweed and linen. Lovely items, but just not me, they make me look 10 years older;
– felt trilbies from Lock and straw/panama hats in various colours and styles. They all look too costumey and make me very self-conscious. And I did give this a fair chance;
– cotton bucket hats. I still take them with me on holidays and they’re very useful, but a bit too nerdy in combination with my spectacles;
– well, baseball caps. I have one from J. Press in ecru with a needlepoint logo, from when I visited the NYC store last year (does that count as a real enough connection?) and a lightweight fitted cap sans logo from Papa Nui in sunfaded red cotton that just fits my head like nothing else. But yeah, it’s red;
– a navy woollen watch cap from Heimat that I’m actually quite happy with.

I’m not dissatisfied with the baseball caps that I own, but I have grown a little tired of the look, especially in combination with any item of tailoring. I’m not always after a high/low or ivy vibe. So are there any viable alternatives I haven’t thought of? I jave looked at berets (like the ones Tony Sylvester sells) but talk about your online menswear echo chamber…


Thank you, Simon. A return to brimmed hats is still in some way what I’m after, I just can’t imagine how that would work with my otherwise well-established wardrobe. But standing in front of Optimo in Chicago not three weeks ago, I almost forgot all about that. They’re such beautiful shirts, I mean hats. 😉


Maurice, have you thought about trying something like a mechanics cap or a version of a cycling cap? Yes, technically they’re still caps. But the shorter brim and the layout of the panels on the crown give them a slightly different character. Plus, like a more traditional ball cap, they look better worn in and beaten up a little. Cheers!


Thanks John, actually I came close to buying a Papa Nui mechanics cap in a nicely faded blue. And I might still go for it because Papa Nui fits me so well. It wouldn’t solve the problem of smarter yet ‘inconspicuous’ headwear, but at least it would feel less, I don’t know, juvenile?


I agree 100% with everything Maurice has said. I’m bald but other than beanies/ watch caps in winter, hats don’t suit me ( or make me too self conscious).
And I’m not quite prepared to follow the Michael Fabricant route in protecting my head!


I completely share Maurice’s views here. I understand Simon’s suggestion of a brimmed hat in winter but no-one wears them these days and I would very feel out of place using one. The best I have come up with so far to wear in winter with my navy SB overcoat is a grey woollen watch cap but even that doesn’t feel quite smart enough. In summer I default to a navy baseball cap but may try a brown, brimmed straw hat which may be less costumey than a white Panama.

Peter K

Another baldy here. I use a Tilley Airflow hat in the summer. It’s less costumy than a felt trilby and gives good sun protection.


Viennese maker Mühlbauer has a kind of minimalist sailor´s cap called Popeye that I wear in summer instead of a baseball cap. They use all kinds of cloth (also MTO), I bought one made of a very thin navy cotton. I find it surprisingly unobtrusive and – as the name suggests – it has a little pop appeal.


My go to hat is a Lock & Co Tremolo, but when I pair it with my vintage Aquascutum overcoat, I fear I am getting a bit too near the dreaded ‘peaky blinders’ look! Now I have started wearing a classic cream RL cap which really softens the look. So despite loving a classic wool bakerboy, I can also see the benefits of a baseball cap.


Completely agree on the wrongheadedness of attempts to ‘smarten’ fundamentally practical, non-luxurious, items. See also the most egregious and sadly ubiquitous example of all – the ‘business’ trainer / hybrid shoe.


I have to disagree about your take on the Loro Piana cap.
Despite their disgraceful pricing I’m on my third and I have the slightly different style/embossed logo that sets them aside from the ubiquitous and above all else I love the fact that they are completely waterproof. I wear mine a lot when I’m out on the water or with my PS Trench when the weather is wet. The two together keep me as dry as a bone without having to lug an umbrella around.


For me, there’s two points here: branding and caps. Taking the topics together, I agree plain caps just don’t look right and some branding is good. As you say, personal is good. But perhaps not a college one if the aim is to advertise ones education (yes, I know you’re an Oxford guy not a Cal tech guy).
But on branding, I feel there’s a snobbery here. And I don’t mean this in “i can afford this” sense. I mean that some people claim to hate branding, when what they mean is the “wrong” branding, So they look down on nike, but up to drake’s. Logically, that’s bonkers. As I age, I find myself anti logo, but still then oddly feel comfortable in a brooks brothers oxford!


I find it funny how varied the opinions are on this subject. That some people see wearing a baseball cap with a jacket as some kind of controversial statement.

I’ve often considered getting another kind of hat, but am resolved to believe that in this day and age baseball caps and beanies are the only form of appropriate headwear for a man.

I think a young man going around in a fedora looks about as ridiculous as going around in a top hat or a homburg or an admirals hat.

And having tried on trilbies and flat caps, my girlfriend winces, grimaces and cringes like I’m wearing something highly embarrassing.

So it’s baseball caps for me, obviously with a logo.


I have to partly agree. I bought both a Fedora and a newspaper-boy hat. My daughter asked me not to appear to football matches with the former because I look like – in her words – „like a clown“. The latter she calls a grandpa hat. However, I would not wear a baseball cap with a jacket. Nobody does that were I live (and this is maybe very different in London) and I likely would draw attention in a negative way, namely as somebody who never wears jackets and does not know any better.


I have a few Ralph Lauren cotton ones in various colors that I love the fit of and they wear in and fade nicely. Also have a couple of random ones (a particularly cool one from the local wildlife refuge where I volunteer). The ease and utility of a simple ball cap can’t be overstated, and as a glasses wearer their ability of keep the rain of my lenses is invaluable.

Zak Wagner

This is great, and I have felt for awhile the no logo caps just seem oddly lacking?
And I would love to have someone bring back local clubs. Having a club, and then in years time an old beat up sweat shirt and hat, would be amazing. I wish I had better taste in College, as it would be fun to have a hat from that part of my life. But I donated them, they were very over decorated and gaudy.


All these years thinking you had studied at Cal Berkeley, even if just a semester.
I own a bunch of ball caps and reserve them for morning walks. I live in Texas but would never wear a cowboy hat, as I have nothing to do with ranching and would feel like I was cosplaying. But on the right man, they can look handsome. I’ve even seen an elderly man at my city gym on a treadmill in denim shorts, sneakers, and a white cowboy hat.
Trucker hats, the ball cap with the mesh back, are very popular out here, primarily because of the hot weather. I have 2, but in solid colors rather than the typical contrast color scheme. Both are from local small businesses. I’m not a sports fan, so I would rather have the logo of a local business that I support.
One thing I will say, I prefer a curve in the bill of the ball cap. A lot of American men under 40 like the flat bill baseball cap, which I find childish looking. Probably because said men are accompanied by a son dressed almost identically.


On the subject of box fresh/how great things age, Ralph Lauren have taken this to the other end of the spectrum with this picture on their website. I would say well work in looks much better than the smart, plain blue cap at the end of the article and underscores the point you make about luxury caps.


Sorry for the error – “I would say it looks much better…” was what I meant.


Idea: a PS baseball cap in navy with light gray logo?

Peter Hall

“measure it against something you already own’

Peter Hall

A wool cricket cap with traditional silk lining would be very nice.Simon.


I don’t think that’d be odd.


Something to differentiate it from “Paul Smith”…


I have a much-loved cap from the Grand Canyon which I bought on honeymoon there (I think). It started as a very dark green or black. It has a park logo on it. It’s now a deeply faded, worn grey-green, partly from hard use in hot, dusty conditions. Wearing it reminds me of the hikes I did there.

Tommy Mack

“I’m not a big fan of the ironic logo, of a made-up club or team.” I thoroughly loathe this trend. It’s never even something clever or inventive, at best an obvious movie reference, at worst just a generic pastiche. Superdry seemed to launch their entire brand identity around this tired cliché (not that I’d ever wear their clothes but they thankfully do seem to have moved away from this somewhat now)


Very insightful thoughts and oddly enough I have been battling with the problem of baseball caps and hats in general as well. I have grown a little bit weary of my basic cotton baseball cap because it seems like there’s no alternatives. I found myself reaching for it too often and as of late, I have started to refrain from doing so. I think there’s a little bit of misconception of how well it works in different outfits. For example, I think you strike a very nice balance of relaxed menswear and usage of baseball cap in your blog post with the RRL hat. That’s how it should be done. However, I greatly dislike the Drake’s look as shown in the photo. I think the combination is quite dreadful and frankly a little bit clownish stylistically. I am definitely not going to judge anyone for wearing a baseball cap, but it does look odd when the formality level of rest of the outfit reaches a certain higher point. It’s taking the high-low dressing too far. It strikes me as the sartorial opposite of wearing a fedora with a band shirt.
Luxury baseball caps also come across as little bit weird to me. Or more precisely, if it’s made out of “fine” materials. If we follow the premise that baseball caps should go together with casual outfits, then the baseball cap material should be on the casual side as well; suede, cotton etc. At one point I was looking for a nicer baseball cap, but instead I have opted to stick with cheap cotton baseball cap bought from the mall without a logo. It serves it’s purpose and I can take it for a hike, grocery store and any foul weather situation. I once ordered an expensive wool baseball cap, but I just ended up returning it.
However, I understand why someone might resort to their trusty baseball cap, be it random dad cap or a Loro Piana one. There’s just not a lot of alternatives. Brimmed hats will unfortunately look weird almost always in today’s culture. Flat caps are a little bit better, but that can be difficult as well and it can easily look a little bit costumey. Still, I have been considering to start looking for a flat cap and try to opt for that instead of baseball caps if the situation and outfit demands a hat. Sometimes a hat is needed, and flat cap can still be quite neutral. Then again, a flat cap would look weird when it’s summer and you need a hat the most. Maybe these problems are just in our head (pun intended). Maybe wearing a baseball cap is lesser of the evils.


I’d agree on Drake’s (a brand I like a lot). Their slightly daft made-up logos on their caps just don’t work for me. I want something plain, tasteful, but which has some nice touches like brass adjusters. Drakes are sailing close to that awful superdry brand.
The best cap I have was from Ampere. A brand I’ve not bought from before (I think it might, gulp, be a bit “cool”).


An interesting article and some very interesting discussion in the comments. I find myself in agreement with much of the article, having eschewed baseball caps for some time, but having returned to them to some degree, after failing to find a satisfactory alternative. I’m still a fan of brimmed panamas in the summer, and would choose either a cap or hat, depending on what I’m wearing – shorts and a polo shirt, or a linen shirt, cotton trousers and jacket, for example. I would never wear a bucket hat; I can honestly say I have never ever some across an instance where a bucket hat looked good (mind you, I feel the same about flip flops, Hawaiian shirts, bowling shirts, pink chino shorts and football shirts, often worn by men in combination with track suit trousers and trainers, which only serve to emphasise the impression that they are strangers to any notion of athleticism or sporting prowess). I’m afraid that I don’t like baseball caps with tailoring. Again, I’ve never seen an instance when I thought it worked (including on PS, I’m afraid).
Winter is a little more challenging. I have some Tremelo caps from Locke, which are great with tailoring. I’m afraid that I haven’t yet found the confidence to wear a Fedora, though a Fairbanks from Locke is definitely on my wish list. After choosing and trying a series of hats which only served to confirm my feeling that hats aren’t for me, the delightful and superbly courteous person at Locke said “would you allow me to choose one for you, sir?” He immediately exactly the right one (the Fairbanks). If only I had the self-confidence (and, perhaps, the budget) to invest in one.
I have some wool/tweed baseball caps that I wear in the winter with more casual clothing, but mostly because I can’t find anything that seems to be a suitable alternative.
I completely agree with the logo preference. Most of my cotton baseball caps have a logo, with personal associations, ranging from a very understated, subtle Fender Custom Shop logo, from my time as a music/guitar journalist, to a Boston Red Sox logo from a wonderful family trip to Boston, one of the highlights of which was a Red Sox – NY Yankees game. I take much the same approach to logos on t-shirts – almost all guitar companies or bands – but I only wear them at home.


I agree that most caps look better with a print. No reason it has to be a logo though. And the versatility of caps with formalwear probably begins and ends with the preppy aesthetic, since it’s such an American thing.

Jack Willimas

Hi Simon,

As always a great article. As an older, much older, man I wear both brimmed hats and baseball caps. SInce they are baseball caps, I wear baseball team logos. And there are different quality baseball team logos that one should notice as these graphic insignias are unique and can be quite compelling. I prefer a Yankees hat, I live in NYC and their logo is one of the strongest yet elegant. My concern, and I have voiced this to you in the past, is the back of a “fits all” cap. The opening above the strap, regardless of material, exposes an area of a man’s head, especially if bald, that is not flattering in any way. Better to wear a fitted cap to the correct size.

Looking forward to meeting you in October in NYC.

Jack Williams


I absolutely agree with your view on the logo. I love wearing a gunner’s cap with casual tailoring. Do you occasionally wear your football club’s cap as well?


Great post! I live in the US (Miami) and often wear my ball cap with a cabana polo or blazer in addition to the more usual casual outfits. In the right circumstances, I find it can help a look from coming off as too fussy. Its also practical sun protection.


Interesting read. Along with a very casual canvas shop tote from a beloved point of sale or institution, a cap is the only place I’ll tolerate a logo. I think you make a critical point about the type of logo, Simon — it should be something with personal significance, and the logo itself should be attractive. I have a few caps that I like, especially a navy one from a small family boat maker in Maine with the name of the company emblazoned in a simple, stitched san-serif font — “J.O. Brown & Son Est. 1888,” it reads. I picked it up on holiday while booking a transit on a ferry Brown operates from its shipyard, and it came in handy while cycling around North Haven during the rest of my stay. Back on the mainland, the simplicity of the design and the obscurity of the source continued to feel very appealing on a cap, at least to me. I also have a few others from places I like…small, independent booksellers in New York, Storm King Art Center, etc.
But ultimately it doesn’t matter how much I like a business or organization; if their logo or the form of the hat itself (an overly high crown, mesh panels, etc.) is unappealing, I won’t put it on my head. And even if I’ve managed to amass a few examples I like over the years, I seldom wear them except in very casual situations where the circumstance (e.g. a prolonged outing in full sun) necessitates their inclusion.
More interesting to ponder is the effect a cap has on an outfit. I suppose you can make the argument that a cap “tones down” a smart outfit in an appealing way, but to me most of the time it feels careless. It’s not as bad as sneakers (of any kind) with a suit, which I view as an abomination that never, ever works, but I still think a cap with tailoring has a similarly poor effect: it just feels misguided, or silly, or something else that falls short of elegant.
Put more simply, I’ve yet to see an outfit that included a cap that wouldn’t have looked better without it.


Simon plain caps are fine. Honestly I think that baseball caps with logos are more low brow and embarrassing. Hats much like hair indicate the mind beneath them. Why would you want to look like a walking bill board, or a brainwashed peon in a logo baseball cap? It’s about as cringe as the Americans who wear rep stripe ties and evoke stolen valor…

James Fettiplace

I think caps are subject to huge cultural associations. In the US, they are accepted by every level of society all the way to the POTUS and wouldn’t be uncommon on ivy campuses. As a Brit, for me, it’s very different. Caps are thought of as a bit of an import, often associated with a fashion angle (usually in a rather negative way as people trying too hard) and as for politics (and apologies to a non-UK audience), who can forget the William Hague cap disaster! We seemed to be sort of primed to have suspicion for caps, ridiculous as this may seem.
Personally, i wear them in the summer with very causal outfits where they are functional, but never with smarter clothing.
But, as ever Simon, thanks for challenging conventions (for us conservative Brits at least!)

William Kazak

As a young man I wore baseball caps. Not now. I have long hair and caps look silly on me. Hats do too. What I will wear, while in the sun somewhere, is a visor. It keeps the sun off of my face. It can have a colorful beach logo or phrase on it.


I wear a ball cap all the time whether sporting casual or tailoring. Truth be told, I do this for vanity sake – to cover my receding hairline. That said, my caps of choice are of high quality (Ebbets Field Flannel makes a damn nice product as does H.W. Dog) and minimalist (i.e. no logos). This is my jam and if it offends the tailoring crowd then that’s an added benefit 🙂


I can definitely see the appeal of wearing a logo of something that you care about, but i still think the look of baseball caps with tailoring to be universally ugly. I don’t see the argument that they “go with everything”, I think it’s quite the opposite: they go with nothing (at least as far as tailoring is concerned). Whenever I see someone wear a baseball cap with tailoring (whether it’s an advert, a style picture or someone in the street (happen’s a few times a year) I think that the look would have been better without the cap.

I can see the practical side, obviously. They can keep your head warm(er) and keep the sun out of your eyes. But they just don’t look good to me – style wise they at best add nothing. Often they fall into the same problem as safari jackets with ties: on paper you add a more casual element to “dress down” an outfit, but in practice the combination is too unusual. The thing with tailoring and baseball caps is that people wearing well-fitting tailoring is ALREADY unusual. You’re already making a statement. Throwing on the baseball cap looks extremely deliberate to me – it always looks like someone who has 50k+ followers on their #menswear IG account trying to make a point about dressing down tailoring. Ironically, the people who pull off the look best tend to look a bit scruffy over-all; I saw a guy yesterday in the subway wearing a too-short tweed jacket, slim chinos (which did not complement his build), chunky sneakers and a very faded cap (not technically a baseball cap, but pretty close). He had a long, rather unkept beard, and somehow for him it actually looked like a natural part of the outfit. It wasn’t a very nice looking outfit, but the cap looked natural.

That said, I understand the selection is quite limited. Watch-caps only look natural during autumn-winter. Brimmed hats are hard to pull off. Flat caps easily look like costume. I suppose I can see the appeal from a practical sense. But aesthetic-wise? Not even Rubato has managed to change my opinion.


Busy week on the work front Simon, so only getting a good read of this now with a mid-week day off and a coffee. Interesting points you raise and I agree. There’s a Japanese brand called Poten, they predominantly make 8 panel ball caps, all the nice trimings, leather strap all cotton etc. I must have bought 3 since the warmer spring weather rolled in, quite pricey. They get the machine wash treatment occasionally when they need it, then I just recondition the leather components quickly. They’re plain, but they definitely have that authentic look. Like something I pinched out of grandads wardrobe, which is what i’m going for.

On the logo front, here’s my problem. The one brand I would wear and I do have a few from back in the day, would now just get me associated with the ‘street wear’ leagues, won’t name it, starts with an S, you know who I mean. However, as an actual skateboarder to this day and someone who loves the brand for the essence of it, it’s 90’s East coast origins, I just don’t feel comfortable with the logo on my head anymore, it’s not the association it was when I fell in love with the brand. The Poten ones are the best i’m going to get I think.


I know, I know, that’s the annoying thing. Actually, I have an old black faded one, it just has a tonal S stitched logo on it, leather strap too actually, better still I think it’s one of the old made in America ones, I must fish that one out.

There are a couple I can think of, just the brand mentioned used to make the best cotton 6 panel caps!


Thank you for this article. I enjoyed it a lot and have found myself, with increasingly hot London summers, relying on my baseball caps more often. Having looked through the comments it is striking how much of an American vs Brit/European divide there is on this subject.
I’m an American living in London and I wear baseball caps when its sunny mainly to keep the sun off my face as I have easily burned skin. I know full brimmed hats are better for this (protecting ears and back of neck) but I often don’t wear one unless I’m to be outside for a long time. I find a baseball cap is perfect for the walk between the Tube station and my destination, and then I can just throw it in whatever bag I am carrying without worrying about damaging it. I have a rotation of 4 hats in navy, orange, green, and white.
As an American, I feel like I can get away with breaking the British & European sartorial rules a bit and don’t mind that it marks me out as “looking American” or the “Ivy style” because, well, those are accurate descriptors of me. Though I put the hat together with my clothes which are more British, French, and Italian in style, thus my personal style is a reflection of my life spent in the US, London, and Europe.
My personal rules for wearing a baseball cap are something as follows:
Always a logo that has a personal connection to me. The universities I attended (a state university and an Ivy league) have very classic logo caps or from a golf course I played and liked.Always with a curved bill as it’s sportswear not a new-from-the-box fashion statement.Always outside. In the American south gentlemen are still taught to remove their hats inside. Furthermore my high school’s dean vigorously enforced this rule such that it made a mark for life.Colors which go well or provide an interesting contrast with whatever else I’m wearing.With anything less formal than a suit.


I find caps to be the best way to show your support for a team or cause.
I have a personal rule that I do not wear a cap that I do not have a story behind. Most of my caps have been from teams I’ve played on, or from events I have attended.
In our world where our clothing is largely devoid of logos, I find that people tend to infer quite a bit from the logo on our caps, and I have found that this is quite often a conversation starter at many events that I’ve been to. The cap that I’m wearing would thus signal my support for a team, cause, or event that I’ve attended, and given the people around me an insight into me and what I stand for.
I’m also a huge fan of the tieless suit with your team’s ball cap when I’m headed to watch a game after a workday. It’s the best way for me to signal the team that I’m supporting without requiring a full outfit change, and also tells me, mentally, that the workday is over, and now I’m able to enjoy a few hours of watching my team do well (hopefully).

Max Alexander

Yet here in Rome, American team logos (particularly those of the New York Yankees) have become a fashion statement obviously unrelated to team allegiance. Beyond Joe DiMaggio (longest hitting streak in baseball history to this day, husband of Marilyn Monroe, son of Sicilian immigrants), I doubt many Italians I see wearing pink Yankees caps (pink? really?) could even name a Yankee, much less how to tell a fastball from a slider. It’s all about the logo. As a New Englander who spent most of his career in New York (and many joyous nights at Yankee Stadium), I take it in stride–life is too short–but I am glad that my son, who also lives in Italy, proudly wears his Red Sox cap.


Very insightful Simon. I’d never been able to articulate why I like logos on caps but don’t like branding on clothing in general. You’re right, it is something about being true to the origin and purpose of the item, which is why made-up logos seem rather hollow. I have a cotton cap that my mother-in-law picked up for free from a buyers club in the US, similar shade to your Cal cap, now quite beaten up, and it looks great with everything. I’ve been asked me where I bought it!


I’m still grieving the loss of my old, battered grey (once black) baseball cap. One of a kind, with a rectangular leather patch on the front with the embossed label: Marlboro Classics and a brass fastener at the back. We’d been through thick and thin, good times and bad times. Like inseparable friends, wherever I went, it followed, always perched on the crown of my head. Until that fateful day on a London bus, that I dropped my beloved cap.

David Spelman

Wearing a hat to rep a place, institution, brand, or club with whom you have a personal connection is so charming. At least it used to be. But the commodification of niche brands by social media has made it hard for me to still do this earnestly. And it’s not just for fake Tennis clubs, of which there are plenty.

For years, I wore a hat with the logo of a hotel near my house in LA (Simon mentioned staying there recently). I have a special connection to the place, which I’ve visited since I was a kid, having grown up nearby. Over the past year, I’ve observed that the beige Sunset Tower Hotel hat has become ubiquitous, not just in LA, but also in other American cities.

In 2022, Frame Denim entered a licensing deal with the Ritz Paris to sell baseball caps with the hotel’s logo in their 16 retail stores in Austin, Aspen, Boston, Dallas, Greenwich, Houston, Los Angeles, London, New York, and San Francisco. Notice what city isn’t on that list.

My angsty 14-year-old self once interrogated unsuspecting schoolmates wearing band shirts, demanding their favorite record or song—knowing full well they weren’t genuine fans. “So you love Megadeth, Robbie?”

For the last two decades, the internet fragmented our culture into niches. However, in recent years, TikTok has been cherry-picking icons from niche brands, transforming them into mass trends, often severing their original cultural ties.

Brands that resonate with a small, influential crowd are now mined for their ability to signal—not a genuine connection to the brand, but rather relevance and proximity. This is maybe clearest with streetwear brands, who today run this playbook intentionally, synthesizing street cred with private equity aspiration.

When I was about 16, I noticed that celebrities in tabloids were wearing sweatshirts from an LA brand called Free City. People online were clamoring for where to get them. Before e-comm, they were only available at the Fred Segal store in LA, and nobody even knew that at the time in most of America. I bought them in bulk from the store at retail and sold them on eBay for a 300% markup to fans that wanted to dress like Paris Hilton – and accidentally discovered arbitrage.

The subjects of this phenomena today are often hyper-local wells of cultural capital (from Place Vendome, Ballroom Marfa) mined for their ability to signal relevance. Baseball hats are one of the most striking conduits for this cultural shift

Of course, you could just wear a hat with your local gardening club, but for me, the charm is often lost because it’s impossible to tell what’s true anymore (not just in baseball hats).

At least this is the case here in LA, where signaling is king. On a recent trip to London, as it often does, my Angeleno cynicism eroded, and I happily sported my Sunset Tower hat.


I think I am in the middle here. I can actually use a baseball cap with smart clothes but never with a suit.
But my question how much thought should go into the color of baseball caps (or a watch cap). Should it match your outerwear, some details (like socks or gloves), your eyecolor or just stand for itself?


I never wore a cap since early high school. Lots of negative associations. But I want to try and keep one inside my Wax Walker in case it starts raining. I shy away from off-white/cream caps because of even more negative associations. Is a black cap ok, or too matchy-matchy with the black details of the Wax Walker, also with a black knit underneath? Similar to this: https://www.permanentstyle.com/2021/09/wax-walker-back-in-stock-and-the-fit-of-vintage-knitwear.html


Since you mention band t-shirts, let me take the opportunity to ask you something that has been on my mind lately: when, if ever, is it OK to wear one? The reason I’m asking is that I used to practically live in t-shirts from obscure punk and indie bands etc. – first, as a student who worked part-time in a record store, later, as a young professor who wanted to stand out a bit from my academic surroundings. However, the last few years, as I’ve been getting more and more into classical menswear, I’ve almost completely stopped wearing them – in part, because I often come across menswear experts saying stuff like “no man over 20 should ever wear a band t-shirt” etc. The problem is, I kinda miss my old punk t-shirts. These days, I basically only use them when jogging, but I’m wondering if it would be possible to incorporate them into my wardrobe again. What do you think, Simon? And what about a separate article on band t-shirts and their place (or lack thereof) in menswear?


Thanks Simon, looking forward to the follow-up, but how about an “if you only had five band t-shirts”, as well? This would of course say a lot more about your taste in music than in menswear, but I’m sure I’m not the only one who would love a little glimpse into your musical preferences!


The last time I checked, I had about 25 (and that was after donating a bunch to my kids, mind you), but to each his own, I guess;-). Anyway: a mention of your favourites would be appreciated!


Last winter I faced a dilemma, wear a beanie or let my ears go cold. I work in St James’ and was walking past Lock and Co, I decided to walk in and have a look. A plain navy wool cap called to me and it’s been a go to ever since. The Sherlock Holmes-esque fold down ear warmer is functionally perfect and ascetically niche in my eyes. 100% recommended.


Any view on wearing baseball caps backward?

Max Alexander

I’m not allowed to wear logos on Endemol TV here in Italy—not even my own vintage Rolex Air King—as product sponsorship has become a major source of production income. Even trainer brands get taped over. Frankly I’m fine with that, I’ve no interest in giving free advertising whether on the air or just walking around Rome with friends. My sole exception is a genuine NYC police department cap, given to me by an officer/tourist, and worn ironically.


Not to bring everything back to Blackbird Spyplane, but amusingly, they just expressed the exact same sentiment as you about luxury caps.
You said: “To me, those caps, often from Loro Piana, feel rather lifeless. Like they’ve had the character and style sucked out of them. In the same way as cashmere denim, it’s the result of someone trying to make a luxury version and removing its essence in the process.”
They said with the attached picture.
The whole article shows how difficult it is to make any universal rules about which logos are “good” or “bad”.


Caps are ubiquitous, but they work. The real sartorial mishap is in two of these photos: the turned up, quarter zip sweater. The uniform of the purgatory that is “Casual Friday”.