Overshirts: Two types, ways to wear, where to buy

Wednesday, December 21st 2022
||- Begin Content -||

Continuing our recent discussion of jacket replacements - chores, Tebas, safaris and the like - I've shot two of my favourite overshirts in order to talk about different types, and how they can fit into a wardrobe. 

The buffalo-check shirt above is typical of a first type: a heavy shirt you can layer over a T-shirt or even a sweatshirt, but could just about tuck in as well. 

Most are flannel shirts, like this, in a brushed cotton - the kind beloved by fans of Americana, who perhaps picture themselves in the woods somewhere, with a thermal underneath and a pair of sturdy work boots.

It's a style that's also been co-opted by various other genres over the years though, including bikers and the general nineties grunge vibe I grew up with, which demonstrates its versatility.

The second overshirt, above, is of a thick felted wool and is more akin to a woollen jacket. 

This type is still cut like a shirt - front placket, sleeve cuff, chest pockets - but it’s more likely to have a straight hem, and there's no way you could tuck it in. It's great layered under a coat, but underneath you'd usually want a knit or a long-sleeved shirt. 

Mine is a little unusual, being an old Boy Scout shirt that's at least one size too big for me - I like wearing in a slouchy, oversized style. But similar pieces from the likes of Pendleton are common in vintage stores, and outdoor brands such as Filson offer them today.

Those modern brands will often clearly separate the two types: Filson has its flannel shirts and, separately under outerwear, Jac-Shirts.

But it can be hard to tell vintage models apart online, such as on the ‘shirts’ category of a Broadway & Sons for example. The best thing to do there is try and get a sense of the thickness of the material, by looking at the images of the collar or cuff. Some also have a give away like a partial lining

While these two types of overshirt are similar in style, and are both heavier than a regular shirt (the biggest reason they work untucked), they're different in how they fit into a wardrobe, with the latter more akin to a piece of outerwear. So I think it's useful to consider them as two different categories. 

Both are definitely at the casual end of our spectrum of jacket alternatives, however. They have no structure, little shape, and a straight front with nothing like a lapel to break it up.

As a result they’ll be relaxed, weekend wear for most PS readers, and that's certainly how I wear them - with jeans or chinos, boots or tennis shoes, T-shirt or a sweatshirt. 

They're robust pieces of clothing, which look better the more they're washed and worn. That buffalo check of mine, for example, is incredibly soft after its years of wear, and I love how the black on this kind of cotton fades to grey, while the red tends towards orange. 

They’re a good choice for those readers that ask about clothes to wear with their kids - they can have many things spilled on them, be washed frequently or simply scrubbed, and look nicer for it. 

I largely wear overshirts unbuttoned. I find if a shirt is untucked and completely buttoned up it starts to look like a big, long block that isn't that flattering. 

If I do button them for warmth, I tend to start with the button in the centre of the chest (as above) before adding others around them (below). 

Even if buttoning all the way up to the chin, the bottom couple are normally left undone, which helps break up that block of pattern/colour. Heavy use of trouser pockets helps too.  

(I feel there's a whole series of articles here, on 'how to wear' rather than ‘what to wear’. Rolling sleeves, popping collars, buttoning on a cardigan etc.)

A couple of other points that I anticipate might come up in the discussion below. 

Overshirts work untucked because of their heavier weight, which means they don’t flap around and look like a regular shirt. Someone asked recently whether I’d wear an oxford shirt untucked, and I wouldn’t, personally. I can see it as a style, but it’s not mine. Most of the time you’re going to look better with it tucked in. 

Linen shirts in the summer are a little different because everything is loose and flowy, and probably because being untucked has an obvious functional purpose. 

In terms of how much it’s worth spending on overshirts, the thing to pay for is the material - no fancy handwork, no extra detailing. Vintage versions are often great for this, if you don’t mind heavier ones being a little scratchy. Look out for those Americana styles or military ones like a CPO. 

Among new brands, outdoor ones like Filson or RRL are good sources. Every fashion brand will do an overshirt, but usually the material is overfinished and not that dense, meaning they won’t wash and wear in as well. 

The Japanese repro brands all do good models, particularly when there’s more of a biker aesthetic - see shirts at Rivet & Hide from the likes of Iron Heart and The Flat Head. American Classics carries new Pendletons, and The Merchant Fox some nice wools and moleskins.

All clothing shown:

  • Vintage buffalo-check FiveBrother flannel shirt, from The Vintage Showroom
  • Vintage red-felt Scout shirt, from John Simons
  • Heavyweight grey sweatshirt from The Real McCoy’s, Ball Park model, medium
  • White T-shirt from PS, the Tapered Tee, large
  • Vintage jeans, Levi’s
  • Suede boots from Edward Green, Cranleigh model, 8.5E
  • Steel chronograph watch, Omega Speedmaster MkIV, tonneau case

Photography: Alex Natt @adnatt

Notify of

Inline Feedbacks
View all comments

You can actually tuck in square shirts. It just depends on the length – the ones I get are usually a bit long, so that’s not an issue. But obviously, the Rivet&Hide ones are just too short for that.
I’m surprised that you didn’t mention Wythe. Their styling is great, but more importantly, their shirting fabrics are the best I’ve ever seen. Have you tried them? Wythe is way over my budget, but the flannels are certainly something I’d want at some point.


Ha…great minds…..I got a Boy Scouts of America shirt last year. Amazingly warm..I felt the fit was a little large but actually similar to yours.

Mind has badges on though…remove them?


You might have to check that the material hasn’t faded


Yes that was a concern…just 2 badges so might keep. Great shirts!

Peter Hall

A flannel shirt I like is the hooded variety. I recently gifted a champion sweatshirt and they fit really well together. Slightly less versatile as they really do look better fastened.

I agree that thicker flannel is much better. Vintage stores are absolutely the best place to look. They fit well into your ‘what should you buy and save for the future” question.


There is a very odd trend I’ve noticed of me thinking about a topic and then seeing it as a PS article a week or two later… it amuses me muchly.
That red felt overshirt looks lovely. Red seems to be a good colour for overshirts. Perhaps more on the grungier side, but I do also appreciate the ability to tie it around the waist when it warms up instead of carrying it around.


Any chance you’re going to steer permanentstyle content wise a little back to its roots of more classic style rather getting deeper and deeper into the casual and street wear realm?


With 3 articles a week, I appreciate the mix of content.


I second that. Casual wear, be it casual-chic or simply “very” casual as above, has gotten much more relevant over the last years accelerated by Covid. Further, suits and jackets/blazers are quite simple as most people are familiar on what to buy and how to wear them. I always appreciate guidance on overshirts, chore-jackets, etc, not only the product but when and how to wear them, including combinations, as I am more unsure in these categories. I think Simon does a great job in breaking this down to the essentials.

Bradley Tompkins

I would say that Manish’s article on chore coats was a good mix compared to this, tbh. Also, the reader feature had a nice mix as well. Cheers.


Nice article Simon. I think you highlight and define this overshirt category well and both examples you have here are lovely, particularly the fading and wearing on that buffalo-check. Looks more like a charcoal x faded red now.

I’ve always had a bit of a thing with wearing anything under a collared shirt, don’t ask me where it came from. I broke that slight ‘phobia’ when I purchased the PS linen overshirt a couple years back now and wore that most days of the week during the warm months.

Now I’m looking for a cool weather alternative, something to stretch my style a bit, as all I wear these days are knits or sweatshirts. I have my eye on a buffalo-check number from the above mentioned Rivet and Hide, by The Flat Head. I hold my hands up, I’m a sucker for that biker aesthetic.


As you are an owner of a RRL western cardigan, have you been tempted by their western overshirts?


Thanks Simon, great piece as ever, but not one for me. I’m shorter than you (by more than I’d like to be) and this type of outfit looks messy and unstructured on me. It’s not flattering and makes me feel like I’m trying to be 14 again (just a smiths t-shirt underneath and the transformation would be complete). So, it’s a mixed one: yes on you, no on me.

Eric Twardzik

Non-overshirt related, but what’s the context of the “Illustrated Ivy” window display you are pictured in front of?

Oliver Price

Private White VC do some nice ones, including the wool one they do with Johnstons of Elgin – https://www.privatewhitevc.com/products/the-luxury-lumber-1?variant=40153735266365


I left my career a few years ago to take over a family business and found myself wearing overshirts/workshirts during the cooler months (I live in Atlanta) even though I had never owned one before. Gustin makes true workshirts as well as regular shirts with thicker fabrics that can be worn as an overshirt and CPOs that double as workshirts as well. Imogene + Willie makes a brown herringbone CPO that I use as an overshirt that I really like.


What are your thoughts of Epaulettes on overshirts ?

I recently saw one with Epaulettes but not all the way to the collar (kind of half way up the shoulder) .
Not sure what the ‘protocol’ is in that .


Hi Simon, unrelated question:

Do you ever find that wearing a jacket + trousers combo actually sticks out more than just wearing a simple suit and tie or suit and patterned shirt?
Especially as a younger guy, I think operating in that middle area actually attracts more attention as most people who want to look smart just go to the more extremes of formality and those who don’t care – well we know what they do.
How do you find a way to strike a balance in this ‘conflict’, i.e. what would you recommend?

Merry Christmas and all the best

Peter Hall

A very good question for a longer article Simon.
Funnily enough,we were watching All Creatures Great and Small ,last night, and whilst liking the wool and tweed combinations up top. my wife was very critical of the trouser colours. Now,whilst not suggesting we dress as a 1940s Yorkshire vets,the contrast was too much.


I think that may be the way to go, I find mostly wearing darker and muted colours helps a lot.

Also worth noting is that if you have clothing that fits well and has a classic cut, you will stand out anyway nowadays.

I think this is because people can immediately tell that you are making an active choice to wear these clothes, rather than adopting a uniform.

This is already unconventional, as the modern uniform are tight blue jeans, sneakers and either a t shirt or inconspicuous jumper on top.

Also highly dependent on what environment you are in, if I were to meet my family for dinner in a tracksuit that would be quite odd.

For others, not so much.


I personally am that guy almost everyday in the office. Most people either wear shirts & chinos, or they wear actual suits (some of those take off their jacket all of the time so they basically wear orphaned suit trousers), or sometimes shirts, jackets and chinos or jeans.
I’m close to the only person wearing separate dress trousers and jackets.

In fact, I’m pretty sure most people don’t even *consider* odd tailored trousers as an option when they dress or even buy a wardrobe, which is a pity if you ask me. Doubly so since most people still keep wearing those terrible elastic chinos with low-ish rise and skinny-hems, but that’s another matter.


I bought my first overshirt this season from Private White and have really enjoyed wearing it. The design is excellent and the quality superb.


Simon, what do you think of this “Ball Park” heavyweight sweatshirt? And how does it compare, in terms of material, fit and style, to the McCoys’ loopwheeled sweat you’ve featured before? Thanks in advance.
Unrelatedly, have you heard of/seen the Japanese knitwear from Wonder Looper (https://wonderlooper.com/)? I’ve got a couple of their heavy weight t-shirts and can wholeheartedly recommend them. Thought you might be interested given the unusual fabric choice.


After recently handling mccoys sweatshirt in clutch cafe, what do you think about durability? Is it safe to chuck them in a washing machine on 40 without a care (No tumble dryer) or i need to pay attention how do i wash them? It felt so soft, almost fragile! Is softness a whole point of loopwhwel?


Hi Simon, you mentioned the Iron Heart CPO shirts: I have one of theirs, it’s western style, 100% heavy wool, black, wonderful with a sweatshirt underneath, v versatile. Style is quite modern not excessively roomy but not slim either. I really recommend them.


Simon, which color do you find more versatile ?


Of overshirts in general. I like your red a lot but with my minimal wardrobe it will not be worn frequently.


I’d really like to see a “how to wear” series. Most men get just as lost in how to wear their clothes versus what to wear, so as far as a rich mine for future material this topic would be highly productive in my opinion. For example, I powerlift and have a much larger hip measurement than most men, so most of my shirts don’t fit properly there. I never button the bottom one or two buttons because of this, and found by happy accident that just as you said, it helps break up the top block and allow for a nice visual transition, as well as allowing ease of access into my trouser pockets without leading to weird bunching of my shirt while I have my hands in my pockets.


Historically I’ve never been big on overshirts, but during Covid I had my tailor make me a bunch in a variety of smarter fabrics (linens for summer, cashmeres for winter, etc) with the intent of wearing them as a “smart casual” option for work since formal tailoring didn’t seem quite as right anymore. While there are a few of these overshirts I could easily wear more casually, like Simon shows here, the fabrics I chose are smarter than what historically has been used for this category, and thus they seem to work better with other “smart” items, like tailored trousers, collared shirts, and high-gauge knitwear and dressier shoes. It feels like a good way to dress up when formal tailoring doesn’t feel right, and (like Simon said) there’s a lot of flexibility to dress this look up or down depending on how you wear it.


My nephew, now studying for his Masters, has just ordered a Tentsmuir flannel shirt by Hoggs of Fife. It is also in a large red and black check, in a weighty 220 gsm fabric – https://www.ardmoor.co.uk/collections/hoggs-of-fife/products/hoggsoffife-tentsmuir-heavyweight-flannel-shirt-hogtent. The snap antique brass buttons and zip breast pockets are very practical features for an overshirt. At only £44, it’s real bargain for those who can’t afford to pay over £200 for brands like Iron Heart or Flat Head.


Iron Heart heavy cotton flannel shirts might be my favorite shirts in the world. I crave cold days in Texas when I can wear them. The unaltered fit for me equals bespoke, and I can’t say that about any other off-the-rack shirt. (My sizing makes bespoke a necessity most of the time.) They come in some pretty amazing color patterns, too. I couldn’t recommend them more highly. And I’m equally passionate about Iron Heart denim, having tried most of the top Japanese options. Rivet and Hide is the best place to buy Iron Heart, whether you’re in Europe or the US.

Bradley Tompkins

Great coverage….I can say this is hugely helpful as when I started my menswear journey I felt that being dressed meant dressed up. At some level that has been a struggle for me. Just recently I have started to intentionally dress down sometimes, but paying great attention to material, fit, and HOW to wear things. To me it is just as satisfying a process as styling and wearing tailoring.

Ned Brown

I was the lucky guy who dated the woman who launched RRL for Ralph back in the early 1990’s. Still have a bunch of the samples after 30 years. Stuff lasts forever. Buttonfly means are the best. Will email you a pic of the red and black shirt. Cheers.


Hebtroco does some great woollen over shirts which are fantastic value. Lots of pockets and cut really cleverly so they work over layers or just a t-shirt. I’ve been really pleased with mine and considering a second at only £150.


Jasper Smit

This looks great, not just the over shirs but pretty much everything they design Thanks for the tip.

Initials CG

Simon, I’m all for articles on “how to wear.” I’ve picked up tips that I would’ve never thought of (buttoning just the top button of the raglan coats or wax walker is something I never would’ve thought of… found it incredibly practical as well as stylish!)
I got way more out of the motor trench trying out some of the ways you buttoned it.
It might feel amateurish stating this but I think lots of guys just don’t take advantage of (or realize) how to wear traditional items in different ways. Popping the collar of your tweed jacket seems obvious, but I forgot I used to do that at school when we were allowed to take our ties off. Looking at old pictures we used to look a little like Ralph Lauren, just more natural and without the stunning girls around us ( all boys school ). Perhaps we forget that even classic clothes can be worn “cool” without too much affectation. Just a thought …
Btw, is the nineties grunge look retro now? I mean, you think early eighties ‘Wham’ style has a shot for a comeback as well?


I own a couple of overshirts or ” shackets” as they are sometimes called. I prefer them if they are more on the shirt end of the spectrum as you can wear a layer over them. If they are too heavy they are really then an outer garment that isn’t waterproof or warm enough. A nice one is a rust Ben Sherman one I picked up for £30 in TK Maxx this week. The weight of the corduroy is pretty hefty and it feels made to last.


I have to be honest here Simon. I only did the top button up to hide a red wine stain! I will take into account the bottom button though!


Shame you missed the excellent choice from Hebtroco. You might want to have a look.


Hi Simon,

On the subject of casual wear, would you have any advice or an upcoming article for what to wear for a young man out on the town? Down to the pub/bars.

I find I’m stuck between not wanting to look too smart, but also not under dressed or too casual.
In my mind I feel there is a middle ground, say a dark pair of jeans (navy), maybe a knit black polo and black loafers or chelsea boots (leather) and depending on the weather a dark coat or jacket but i’m never quite sure where said ground is.

I want to look stylish with that “edge” that a leather jacket often gives you, hence the black/dark colours mentioned above. Hopefully this makes sense?



Hiya Simon,
I would and have but largely if I’m going out for dinner or perhaps a date. If I feel overall that the evening is going to be more refined and requires elegance then I’ll wear something accordingly.
I’m looking for something that would be more casual but could be seen as smart because it’s stylish – not necessarily formal. Something that utilises high/low dressing. Definitely more than jeans and a sweatshirt.
Off the top of my head I’m thinking along the lines of a popover shirt or polo and trousers and an “edgy” jacket ie leather or denim but I’m not sure.
Taking inspiration from one of your previous posts “wearing all black” (https://www.permanentstyle.com/2022/08/wearing-all-black.html) perhaps a combination of blacks, greys and dark blues in various fabrics for differentiation in textures?
Ultimately I’d like to look elegant and stylish in said bars without seeming over dressed. I don’t agree with the perception but I could turn up in one of my favourite unlined blazers with a shirt and chinos/jeans and be viewed as a bit “Dad” or old fashioned. Suppose it’s all down to context/situation.


Thanks Simon!

Steve B

My suggestion might be what I wore at the Plaza in NYC; a pin stripe navy overshirt with matching drawstring trousers, it felt not too casual but smart enough & very comfortable


What i found sort of works for me when i want to dress up but avoid “you’re going to wedding?” type remarks is smart trousers (In my case double pleats and cuffs), smart shoes with something knitted on top (shirt collar polo, knitted polo/knitwear) or chinos with a tailored jacket over knitted polo/shirt collar polo/oxford. Somehow i find tailored jackets much easier to wear in a temperature when they can be worn for warmth, not just for style… in summer i really struggle to wear a tailored jacket, but linen overshirt seems just fine.but than again im not too young anymore.


Thanks Martins.

Yes I have some charcoal houndstooth trousers which paired with a dark knit and smart shoes could be a nice combination.

In lieu of a tailored jacket, maybe it could be a dark suede jacket like a valstarino?

In summer I’m a big fan of linen bombers or field jackets, unless I think I’ll need a tailored jacket (linen too).


Blessed Christmas Simon, your family and PS Team!

Hello Simon. I’m buying these as my Second Overshirts from The Real McCoy’s https://therealmccoys.com/collections/tops/products/shirt-cold-weather-field-wool-nylon. I intend to wear it over my Japanese T-Shirts / PS Denim Everyday Shirt / T-Shirt / Chambray Work Shirts Indigo with my Blue / Indigo Jeans and Fatigue Trousers Olive. Please let me know if my styling and thinking makes sense to you?


Hello Simon. I hope you doing well. I was looking at this https://standardandstrange.com/collections/orslow/products/orslow-fatigue-shirt-olive-reverse-sateen. God willing I intend to buy this as my third overshirt. I’ve really taken a liking for overshirts (most casual in style) as an alternative to jackets . I like styling and wearing overshirts according to my own lifestyle and personal preference. I find overshirts comfortable and easy as opposed to jackets / shackets.


Thank you Simon. No questions about the jacket. As of now I like styling and wearing overshirts according to my own lifestyle and personal preference. I find it comfortable and easy to style overshirts.

robert e gault

Situated in the west coast’s moderate climate I live in my shirt jackets/overshirts. I have a selection of vintage wool Pendleton, Woolrich & Filson and bespoke tweed or linen ones. I throw then on over a henley or an oxford cloth button down to dress it up a bit. In the colder weather (yes it does happen) I have vintage Norwich tweed jackets that withstand the cold/wind/rain. And on the really cold snowy days….I stay home.

Steve B

Hi Simon,
These heavier duty overshirts have been a staple whilst in NYC over a cold Christmas there. Mine thankfully had a thermal lining too which helped against the biting winds & was buttoned up & under a ski jacket & so I was as warm as toast. . I also found the chest pockets were a little more roomier to comfortably take passports etc. Glad to see the links of other American brands, thank you.


Inspired by your post I tried to find an overshirt. The iron heart, which indeed was quite nice, but was (in my eyes) overpriced. I decided for a more uncommon choice and bought Fjällraven’s Canada shirt, which I really can recommend.
I know, that this is normally no brand to cover here. But for the purpose of being on the playground with the kids and making campfire with stick bread and marshmallows it seems to be the right choice.

Best regards


I love my McNair merino shirt. Mine contains a little note that says it was made by Irina at their factory in Yorkshire, which I think is a lovely touch. It’s nice and cosy, can be worn under my wax cotton jacket and is beautifully made. In fact I’m wearing it now.


Hi simon do you ever experience yellowing in your white tee ahirts? Especially when you havent worn them in a while


Simon, you mention that the sweatshirt here is large but in the comments on the article about quality sweatshirts, you mention you were a Ball Park medium. Do you have one of each? I’m asking because it helps in gauging the style. Based on the measurements the Ball Park sweatshirt should be fairly boxy and not at all slim.


This post inspired me to buy a heavy cotton flannel shirt from Filson. It is great but the thickness of the cloth means I can´t wear it comfortably with my slimmer pants. So I am thinking of having it shortened and wearing it untucked as a shirt jacket. Would you go for a straight hem? (There are overshirts clearly not meant to be tucked in with a curved hem from makers like RRL.) And what would be a good length? Yours look quite long (even the checked one which otherwise doesn´t seem oversized), certainly longer than most on Rivet and Hide´s website.

Michael Gargiulo

Hi Simon,
Regarding the lining, are you saying here that the genuine vintage ones are likely to NOT have lining?
I found one line I rather like, but I was concerned that the lack of lining may make it fussy to deal with as a layering piece.
It is a zippered jacket as opposed to an overshirt, but still unlined https://wooden-sleepers.com/collections/products/products/vintage-buffalo-plaid-wool-jacket?variant=40935334314054


Oh I see, thank you!


That vintage wool jacket is still being made by Johnson Woolen Mills. You can buy it brand new for about the same price. I have a couple of them,one lined with cotton and the other unlined. Both work for me. They do run a little small in the chest and shoulders.


hi Simon
my question is about flannel shirts.
what are your favourites?
I see quite a few on the Marrkt site from respected makers like Warehouse and Pherrows and of course the Real Mccoy .
have never worn buffalo check but wonder how to combine such so as not to look too casual and yet essentially casual. Say going to a cafe, restaurant or round the shops.

Advice much appreciated


I get the slouchy look you want and the sizing up, but what length should the overshirt be?
I wonder whether these are often too short. Should they cover the seat? I quite like the idea of inside pockets too.