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The biggest potential pitfall with tailored dressing is looking fussy.

Fussy is not sexy; it is not attractive. It is closely related to appearing ‘affected’ or ‘mannered’.

Looking relaxed in clothing, on the other hand, is very attractive. It lies at the core of terms such as sprezzatura, grace and elegance.

It is why Hardy Amies told us to forget all about our clothing, once we had put it on.

I would argue this is at the very core of dressing well as a man, and is the thing sartorial dressers most frequently get wrong.

Fortunately, there are many ways to achieve it.

The first is dressing more simply, or avoiding anything that you feel you need to fuss with. The second and easiest is just being at ease, but this usually comes over a long period of wearing the same things. And a third is deliberately having some aspects of your dress imperfect (sprezzatura).  

Here we will look at a fourth: mixing casual and formal elements together - sometimes called high/low dressing.

It is not the easiest way to avoid looking fussy or mannered; indeed it is easy to get wrong.

But it is perhaps one of the most stylish way.

One guiding principle for high/low dressing is to play with the accessories, not the core. So outerwear, not jackets; shirts, not trousers.

A second is to be aware there are grades of high and low, which should not be pushed too far apart. So a Barbour jacket with a casual suit, but not with black tie.

The further apart these two extremes are, the easier it is to get it wrong.


1 Outerwear

The easiest and by far the most popular way to add casual, or low elements to an outfit is with outerwear.

Examples of casual (and often cheaper) outerwear pieces that can work well are:

  • Waxed/hunting jackets (Barbour, on Jake below, often being good because many are long enough to cover the full length of the jacket)
  • Duffle coats (Gloverall’s Monty - above - being the classic, but there are lots of other options)
  • Tweed/raglan-sleeved country coats (Smarter, but still definitely more casual than a tailored overcoat)
  • Cotton army coats (Largely field jackets like the M-65, and at a stretch a fishtail parka)

It's easier to look casual and unfussy if the coat is a little beaten up, which leads to a lot of men buying them vintage.

If the fit can work on you, that’s fine, and certainly better than buying artificially aged versions from designer brands.

But be careful with the length. For example, I love my vintage M-65 (shown in the introduction) but my height means it is too short to wear over a tailored jacket.

The issue there is milder version of short gilets over jackets. This is certainly a look, and I can see why some people like it, but for me it stretches the high/low separation too far.


2 Shirts

Second easiest is the casual shirt. Two examples of this have been ubiquitous in recent years: the denim shirt and the polo shirt.

One extreme of the denim shirt is the thick, pearl-snap cowboy shirt (above). The other is the Everyday Denim shirt, which is closer to being a dress shirt that fades nicely.

Mostly it’s safer to have something in the middle - which is obviously denim, but still functions well under a jacket (above).

My advice here would be to never sacrifice fit points (eg long tails to tuck in, collar at a decent height) but feel free to play with the colours, washes and design details.

On the polo shirt, of course, my favourite is the two versions of the Friday Polo I’ve offered here on Permanent Style. But many others, particularly The Armoury (above), offer really nice versions to wear with tailoring.

It subverts the assumptions of tailoring in exactly the same way as denim, but if cut like a regular shirt, mostly just shows in the material and texture.


3 Accessories

Accessories are one of the easiest things to add an outfit, but don’t tend to make as dramatic difference as outerwear.

A beanie that sits close on the head and retains a clean look (above) can be nice with tailoring, and is a big contrast to the alternative of a fedora or trilby.

Caps sit somewhere in between.

Colourful scarves, such as those from Drake’s, Liverano, Rubinacci and others, are not so much more casual and ‘low’ as more fun. They’re colourful, more playful, and can soften tailoring in that way.

They can also be a little flamboyant though, and if anything I tend to prefer more muted scarves such as indigo dyes to achieve the same effect.

I also often wear, as shown at the top of this post, Hermes silk scarves with coats and knitwear.

If anything this is high/low the other way round: the fanciness of a silk scarf being brought down to earth by a wax jacket. 


4 Shoes

A difficult area, largely because guys want to wear trainers with everything and it rarely works.

I’ve covered this in detail in my posts on how to buy and how to wear trainers, but in summary:

  • For a trainer to work with tailoring it must mimic some aspects of a dress shoe. Specifically long, clean lines, plain colour and a simple design.
  • They are best worn with more casual tailoring. So a cotton suit rather than a worsted suit, and most often just smart trousers, without a tailored jacket.

Most of the time, the best way to use shoes to look more relaxed is to just wear them - so they get worn in, look much loved and a little beaten up


5 T-shirts

A T-shirt under a jacket is a favourite of fashionable types, but rarely works.

If you have anything but a short neck, it will be much less flattering than a collared shirt. Also not great for the jacket collar against the skin.

In general - although not as casual - a rollneck or polo-collar buttoned up to the neck will be more effective. 

If you do want to try it, go for a lightweight crewneck sweater underneath the jacket, rather than a T-shirt.

If it’s in cotton, it won’t be much warmer than a T-shirt, and it will make the neckline much smarter. John Smedley even does short-sleeved cotton knits in the summer.

Wearing a slim scarf underneath (as shown above) the jacket can help, as it will create a substitute collar at the neck, and follow the lapels of the jacket nicely.


If you want to try something along these lines, I recommend starting with outerwear.

Wear a sports jacket and flannels into a vintage store, and try various things over the top of your jacket, to see how you like the look.

And don’t be fooled by magazine shots. If you think someone looks good in a T-shirt and jacket, cover up their good-looking face and athletic body, then reconsider.

Photography: All Jamie Ferguson except silk scarf/D-43 and indigo scarf (both Drake's), white trainers (James Munro) and T-shirt (Gieves & Hawkes)

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Hi Simon,

thanks a lot, this article is clearly a staple. Being overdressed is often a nonsense, and may make you look like a cosplayer. For a classic menswear enthusiast, you have to be able to mix tailored pieces with more casual things, and you succeded in giving real pieces of advices in this perillous exercice. I had a very good time reading your article about going formal from a casual outift, and this one is on par. Needless to say it’s inspiring for my works. I look forward to read more article on this subject. Thanks again for your work!

Nick Inkster


I have a blazer in a dark royal blue which I originally commissioned to pair with flannels in various shades of grey, but regularly wear it with beaten up jeans, and they sit together very happily.


Well on the subject of cosplay then buying in to the Street style of baseball cap, athletic shoes, Grey jogging bottoms and some type of hoody will also often look like cosplay if a man is not from a certain demographic or part of a Los Angeles Street gang. Possibly even worse is not really having any style at all! just looking in between styles.


I wholeheartedly agree. Posts like this one and the one of different scales of formality are the ones that are most applicable and useful for most of us. While the product and tailoring commisions/reviews are lovely, I’d argue that most guys today will find more relevance linked to their day to day life from these kind of articles.


Great idea. That scale will always be different depending on setting, country, culture etc. but I’m sure it would be appreciated.


I think the key thing is looking and feeling comfortable in your own skin. Its why some hoorays can wear red trousers and tweed jackets and look absolutely fine, but some people try and emulate it or “live up to” that look and look extremely stiff, buttoned up and out dated. I think it very much comes across when people seem to dress “aspiration-ally”, rather than concentrating on what looks good / what they feel happy in. Thoughts?


I thought sprez was *supposed* to be accidental


Great article! I’ve observed lately that perhaps the most extreme version of high/low dressing outside the classic menswear community is found at trendy bars, nightclubs or restaurants.

On the one hand you notice the occasional dinner jacket – but they are worn with jeans and you certainly wouldn’t see a bow-tie. There are suits, especially with Mohair, but an English military cut would look totally out of place. Tweed or Linen feels too “day-time”, as do tan shoes, even though this would seem the appropriate level of formality.

I think the sort of thing I’m talking about probably comes from the mismatched combination of dark night time colours (which are traditionally more formal), smart-casual dress codes (generally collared shirt, jacket, no trainers), and a preference amongst modern men for appearing as casual as possible.

Still, given that part of being well-dressed is about not standing out too much, I’d be interested to hear how you navigate this sort of dress code.


H, if I may, have a look at Saman Amels latest knitwear lookbook, or by all means Stòffa’s instagram for slightly smarter inspiration. While the cut of trousers might be a bit fashionable or bold in the SA lookbook, I think it it’s a very good proof of concept of how far you can go with tailored trousers and knitwear.


With regards keeping your head warm whilst wearing a suit / jacket what would you suggest ?
A hat seems too strong a statement piece whilst a beanie feels too casual .


Keeping with the high/low theme, perhaps an “informal” hat rather than the dressier options that would be more “correct” with a suit. I rather like a Tyrolean hat. But yes, anything other than a beanie to keep your head warm seems like a statement.


Extremely helpful article, thank you! The length of casual outerwear is definitely something to watch out for; I have a Barbour and a Gloverall and neither comes close to covering a jacket underneath (I have a relatively long torso) which is real shame as I love the look.


It’s a slightly reworked version of the Monty I got from Epaulet, with narrower body and, yes, probably shorter length, thinking about it…


“And a third is deliberately having some aspects of your dress imperfect (sprezzatura).”

Surely the very definition of affectation and by extension ‘fussyness’?


Sprezzatura seems to have reached a point where hardly any of it looks accidental or natural. The narrow blade of the tie being longer, the undone monk straps, the unbuttoned button-down collars, rolled up pant cuffs, are all so overdone there is no elan to it. The only example that seems to have survived is the unbuttoned shirt cuff while wearing a jacket.



Do you know any shops that carry Gloverall Monty in London?



Thanks Simon. Is the Monty really the most classic Gloverall duffle coat or is it this one: https://www.gloverall.com/mens/men-s-mid-length-duffle-coat.html

Which do you prefer?



hey Simon what do you wear under one of those roll necks. Always been too embarrassed to ask anyone! Do you put a T shirt under there? Does the actual roll neck not become dirty being in contact with your neck?


The fundamental issue for men’s clothes is are they fashion, like women’s clothes. At their core, the answer is a simple “no”. We like ‘tailoring’, which INHERENTLY means we are no fashionable. Simon is the best guide to most beautiful tailored clothes, but they are not fashion. Fashion = sexy. One could not possibly mount a great show at the Met Museum using (contemporary) men’s clothes.


Somewhat unrelated question, but what colours/items do you often find yourself wearing natural/biscuit/light brown ties with? Aside from navy blazer/hour shirt/grey trousers etc. I’ve liked mine with a mid brown blazer and Chinos.


Simon, lovely western denim shirt you have there! Who is it made by?

David Wenlock

Hi Simon, I’m not sure if you’d call this a high/low outfit, but I recently saw a guy in a dark, tailored velvet jacket, tapered stone-coloured chinos and a white shirt. A combination which I thought looked great for an evening on the town


Context matters when it comes to what looks “fussy.” Here in the US, for example, a jacket, shirt and tie, except in urban centers and a few towns—primarily in the E Coast and near Universities—signals formalness undisguised by a duffle coat or unbuttoned button-down collar. Unless you’ve come from an IPO, bar mitzvah or some other formal affair, locals will likely deem you fussy (read: strenuously overdressed).

Also, a bit of contention with your suit & t-shirt preference. A slim-cut suit with rolled sleeves, a v-neck T (in stretch fabric that lays flat and sharply) and loafers/trainers is a magazine look that I’ve shamelessly adopted for evening and weekend urban outings. It’s not just the length of the neck that matters but also its thickness and proportionality to one’s head and torso: not for everyone.


A superb article, Simon – thank you!

What is you opinion regarding camel hair sports jackets (camel or black color) with jeans and brown suede shoes?

What do you think of casual suits (not pinstripe, etc), and open shirts?


Even “knock-abouts”?


Interesting article and some good examples of what works.
The eighth visual with the polo is a masterful look (Simon – do you know who made the suit?) as is the thirteenth with the roll-neck /suit combo.
A masterclass on how not to do it is visual twelve (round neck T shirt with or without scarf looks good on nobody and is the domain of the boy band) and the final visual is for the view and laugh file.
Also Simon, I could only support this trainer/trouser look if you had a tennis racket in your hand !
Overall so good stuff and it’s interesting how strong the inspiration of the early ‘70s is with some of these looks. History repeats itself but not in exactly the same way. This time around we have better fabrics, better tailoring and thankfully, were appropriate, better haircuts! Tommy Nutter would have loved it.


Hi Simon,

I really like the boots in the third photo while seated on the bench. May I have the colour scheme or brand?


Sid Pharasi

Simon – Grey flannel trousers – to cuff or not to cuff? I got a versatile mid grey pair from a men’s MTM shop in Toronto (Spier and Mackay). Slim fitting, mid rise. I plan to wear them with Navy blazers and OCBDs for business, mostly derbies, dressy chukkas, or sleek captoe boots and hopefully dress down with white sneakers and shawl collar cardigans, hoodies. I definitely want to go with no break, and a taper below the knee. How wide should the cuff be? 1″? 2″? Thanks for your advice…


Funnily enough I’ve been having the same debate with a pair of pair grey flannel Rota MTOs I just received today. So you’d say cuffs are more casual? Somehow I’d have thought the opposite. Also, would you still do cuffs with no break and a tapered leg? I feel like they might look a bit schoolboy like with the cuff flapping about above the shoe…


PTUs are a standard feature on a formal suit. Odd trousers in flannel and the like should be finished with a military hem.


Can I wear blue socks with gray trousers or is black better? My shoes are brown mostly but sometimes black too and I am often wearing my tan sport coat with a green short to go with it. Just asking.


I’m glad you brought up the duffle coat which gives me a chance to ask a question regarding it’s formality. I’m debating wether or not to get one as a winter coat for quite some time.
I’m on my last part of lawschool and will continue to work in a mix of university and court environment for at least another two years after that, so a relatively casual enviroment.
My “uniform” is generaly OCBD and chinos/grey flannels, depending on the weather or event with a shetland or blazer on top. I would love to get a camel hair polo coat but fear that it’s too formal for this environment.
Do you think I could “bridge the gap” with a duffle coat (I consider the classic Gloverall in navy in the tall version for the overall longer legth with arms shortend) or would this seem too youthfull/unprofessional and I should consider a more formal alternative?


Very helpful write-up and some fab photos – esp. the one with the biscuit tie. I am not that keen an your colourful silk scarfs as they seem a bit fussy to me – but as many things, fussiness is in the eye of the beholder.


Enjoyed the article which so nicely demonstrates the paradoxical nature of style. It’s an effort but the effort shouldn’t show. Surely your second method (wearing the same things over and over again) is the most cost-effective and probably most natural of them all.
Plus, even discounting the routinization effect they have on the individual, clothes that are a little worn look inherently better.
Note also that the high/low effect is an added incentive to wear more things one already has, which in turn adds to the “routine” component of style.


Really good work! Enjoyed reading it…the article is the perfect match to your previous one called „sliding scale of formality“
Have a nice sunday and reflective second Advent!


Excellent article Simon on a very important topic for us who love nice clothes but do not work in the banking industry

Rafael Ebron

I liked Barbour. But then someone here in the US turned their wax jacket into their signature piece and kind of ruined the brand for me. I’m sure you can guess who I’m talking about.



It seems some of your readers disagree with you on how much *deliberate* nonchalance is permitted under the definition of sprezzatura. I believe what is acceptable has changed over time… from “A man should look as if he has bought his clothes with intelligence, put them on with care and then forgotten all about them.” (Hardy Amies) to “To achieve the nonchalance which is absolutely necessary for a man, one article at least must not match.” (Hardy Amies again).

I had expected that you would err on the side of tradition, i.e. that sprezzatura should not BE deliberate. It appears, however, that you merely think it should not “look” deliberate: how modern!!

Perhaps a longer form opinion piece should be called for.

Happy Christmas,



Good topic! This is my way of fitting in or feeling contemporary if you like. I like to wear traditionsl clothing, but in Sweden you look apart if you are not very casually dressed. Jeans and t-shirt. On a more positive note this is also how you can develop your own style. Blogs on style easily feels very suffocating. Full of rules and anxiety. Bring back the fun and playfulness.


Thank you and I hope very much you may want to develop this topic with more ideas. I have myself turned to American worker boots in oiled leather and now lately oversized sweaters ( for example in the style of the brand The elder statesman) combined with smarter garments. Suggestions there would be nice.

Ulv D.

Maybe a small item – but that ribbed beanie looks quite lovely. I believe I have seen you wearing a similar one in grey, too? Can you share the model?

Gordon Ang

Hello Simon,

Any particular brand you would recommend for the Duffle coat/ Raglan coat ?

Thank you


I was wondering if you could recommend any tailors that work in a 90s Armani style: unlined, drapey, no waist suppression, big lapels, etc. Thanks!


Hi Simon,

I’ve always wondered if double-breasted suits lend themselves as easily to more informal accessories as single-breasted suits. I have on my mind particularly patterned shirts, especially subtle blue ginghams and glen checks. I’d say that if paired with a navy or charcoal DB suit and rather conservative tie and handkerchief (to keep the outfit otherwise simple), particularly if the shirt has a slightly higher collar, it could look very stylish.
Or is a double-breasted suit inherently more formal so it is not good thing to play with shirts (and stay with solid white/blue) but rarther with subtle ties etc.? What is your experience?

Thank you!


Martin F

Stumbled across this article and it provoked a thought: How does the concept of not looking fussy, not looking to studied, looking effortless and that of sprezzatura relate to a mirror shine on shoes? I mean, a mirror shine cannot by its nature be “effortless”. On the contrary it requires quite an effort to achieve. Something that I am quite certain that everybody, not just those into menswear, certainly grasps. Does this mean that a real nice mirror shine on your shoes per se projects that the wearer is indeed a bit fussy (and studied) when it comes to his clothing? (And perhaps makes it impossible to project true sprezz?)


Aside from trainers, what other shoes would you recommend?


Hey Simon-

Found this archived essay linked from your post on “Hats with Coats”. Providing links to your archived essays is really helpful.

Can you offer an opinion on a jeans jacket? I’m trying to find uses for vests from my 3 piece suits. Was considering OCBD with vest, stone chinos and jeans jacket? Seems to fit high-low.


Thanks. My vests are destined to accumulate dust in the closet. Ha Ha. Great stuff as always.


Hi Simon,
Could a navy Private White Harrington work with a pair of tailored cotton trousers along with shirt,perhaps a polo shirt?
As for tailored cotton trousers colors for a more casual wardrobe ( weekend wardrobe) what color do you recommend after a light beige? Something that could be versatile especially with navy?

What about the weight of a cotton trouser?
Rota is offering two cotton fabrics in different weights ,430 gr (winter) and 320 gr (summer). I do want to wear the trousers during fall but also in summer. I am thinking that the lighter fabric won’t pair well with heavier garments, peacoat for eg. What do you think?

Thank you!


Hi Simon,
Do you think that this denim chore jacket from BHL could be worn with tailored cotton trousers? More as a high/low dressing.


This comment is really late, but for me this is one of the greatest articles here and I just discovered it now. 
You mention the two options military field jacket M-65 and (Barbour) wax jacket. I like both options (Barbour Beaufort/ e. g. Drakes stocks a waxed field jacket). I see field jackets much less often over tailoring though. Barbour Beaufort also often look a bit boring/loveless without accessories like hats and scarves.
Are there any fundamentals to consider between the two options? 


Hi Simon!
Most of the people around me can be seen wearing t-shirt or polo, jeans and sneaker as regular outfit.
Now if wear Henley t shirt with chinos and suede loafers. Would you consider it a high low dressing because of the casual element of t shirt and formal elements like chinos and suede loafers?


Yes my only aim should be to be dressed stylishly.
Thank you for the advice Simon!
Do you consider Henley with chinos and suede loafers a good look?


Hi Simon!
Your opinion on Polo t shirts worn tropical wool trousers?
I tend to do it sometimes and I feel I do pull it off well.


Just read an article which referred to an all fitted outfit as very fussy and adviced on having atleast one garment oversized.
Personally I do not find oversized garment that appealing.
What is your opinion on it. Is it required?

Kailash Chamaria

White trainers have become so ubiquitous that I have started to move away from it.
Suede chukkas can be a nice alternative in spring and autumn but unable to find something which can be elegant and refined to wear outside in summer.
Could you suggest some nice alternatives to white trainers in Summer?
EG suede Loafers?


Simon, a wonderful article to which I keep coming back. Thank you for sharing this info. A vintage peacoat might also do the trick for a casual coat in my opinion.
I would also add what I learnt from Brian of ‘He Spoke Style’, that blending tailored pieces with casual clothing is also another way to approach high/low dressing. For example, a tailored shirt and dark denim paired with smart shoes but a causal jacket can be classified as high/low as well. This is my interpretation though.


Thank you Simon. I appreciate the take on High/low vs medium. If you wouldn’t mind, can you please give me a few examples of medium clothing articles? I ask because while I appreciate the effortless elegance of high/low dressing, I’m looking to try more of medium style in my wardrobe. I would appreciate your inputs. And, Hope you have been a great new year! Wish you my best!


Is Alden LHS suede loafers with workwear chinos an example of high low dressing?

Tim Lynch

Interesting article. Quite a helpful lesson in high/low dressing, Simon.
The principle used in this post to keep the core pieces and only change up other items is imperative here, I reckon. I have a question. How do you define core?
And, thank you for this post. Fantastic stuff. In fact, the entire website. Cheers!


Thank you for your incredibly helpful posts Simon, and for the discussion in the comments. I am very new to dressing intentionally, and finding joy and expression in the process. PS has been a huge help.
I read your article as saying that jeans with a sport coat is hard, maybe too far apart. I really like pants on the very casual side (worn jeans in a lighter blue or cream, less smart chinos, corduroy trousers). But also really enjoying wearing a sport jacket for the first time as I love how flattering the shape is and feels like a statement that I care how I dress, even while wanting to keep a casual look. Do you think there’s any way to reconcile these things? I’ve got my eye on a warm brown houndstooth jacket that I think is beautiful but worried it will just look off with the pants I like to wear. Thanks!


If I wear a smarter poplin shirt with tailored trousers and instead of a wearing a smarter jacket I wear a casual bomber jacket in its place then would it be a good high/low dressing or is too far apart in terms of formality?


In terms of shirts would a chambray shirt also have the same effect as a denim shirt?


Would changing the trousers to dark wash denim also help it in being unfussy?


As a discussion, if someone is to wear a jacket with shirt but with jeans rather then trousers then could that be termed as high low or in a way unfussy?