The Essential Fall/Winter Menswear Wardrobe

January 19th, 2015

Our “20 Menswear Essentials for Spring” article was a big hit. So here is the equivalent for the Winter season.

In a perfectly curated wardrobe, all of the pieces (well, almost all) should make sense together and be interchangeable. For example, each of the ties should work with each of the shirts, and each of the shirts should work with each of the trousers. In theory, you could get dressed in the dark. Using only the 20 core pieces below you should be able to create dozens of different outfit combinations and be appropriately (and stylishly) dressed for just about any occasion.

Before you start stocking up, though, keep in mind that (as always) we recommend buying quality. Well-made clothing lasts longer and looks better every time you wear it, so it works harder for you and saves you money in the long run. These are all classic foundational items that you can wear for the next 10+ years, in my opinion. Think of them as investments. Investments in your appearance, your first impressions, your confidence, your sexlife, your career, etc.. It might take you a couple years to build a high-quality, well-edited wardrobe. That’s okay. Menswear is a marathon, not a sprint.

1. Medium Grey Flannel Suit

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A grey flannel suit is the foundation of your F/W tailored wardrobe; it can be worn as a suit, a sport coat, or a separate trouser.  Look for one that is medium grey in color with a nice beefy texture and have it sharply tailored.

2. Brown Patterned Sport Coat

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This can be any number of winter-ready fabrics, like donegal tweed, herringbone, or a houndstooth/windowpane like this unstructured flannel piece.

3. Navy Tailored Overcoat

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A classy gentleman’s coat is a must, like this midnight navy, double-breasted, peak lapel number. Make it 3/4 length and have it tailored with just enough room to fit over the flannel suit or textured sportcoat.

4. Brown Leather Bomber

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You’ll need a more casual coat as well; this is it. Medium brown, waist length, padded for warmth, with a jet-pilot-inspired mouton collar (this one is removable).

5. Navy Peacoat

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Outerwear doesn’t get much more classic or versatile than this. Look for one that is trim cut, double breasted, hits just below the seat (preferably a couple inches longer than the suit jacket/sport coat) and has a collar that stands at attention.

6. Tweed Waistcoat

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The separate waistcoat may be the most underrated piece in menswear. In a thick cloth like this brown donegal tweed it offers the body warmth of a sweater without the bulkiness in the arms, and with more of that old-school gentlemanly charm.

7. White Oxford Shirt

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The most basic shirt a man can own. It’s a healthy cross between “dressy” and “casual” and a blank slate to create any kind of outfit around. Look for one in a beefy cloth with a trim fit, high armholes, and a button-down collar – like this one.

8. Blue Striped Business Shirt

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A man cannot have too many blue, white, and blue & white stripe shirts. Start with one that is white-based with light blue stripes, like this. French cuffs are optional depending on how formally you dress for business. Remember to have it tailored to fit properly, which may include adding darts.

9. Rugged Denim Shirt

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The blue stripe is your formal business shirt, the white oxford is your middle ground, and the rugged denim shirt is your casual go-to. This should be the only shirt short enough to wear untucked. I like a western style in a thick rugged denim with patch pockets, like this one.

10. Shawl Collar Cardigan

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Don’t be fooled, the grandpa sweater can be a sexy layering piece in menswear, especially in a soft wool or cashmere. Look for one with a marled multi-tone texture in a neutral color, like this black/white/grey.

11. Basic V-Neck Sweater

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This is an easy one. Solid neutral color, thin, fitted, and preferably with a deeper neckline. It should be snug enough that it fits under your suit jacket and sport coat with no difference in fit.

12. Thin Turtleneck

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Another underrated classic. Look for one in a neutral color that works with grey, brown, and navy blue. I recommend a light brown, camel, or a forest green like this one.

13. Selvedge Indigo Jeans

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A slim straight-leg (or slightly tapered) jean is a must have. Look for one in a rigid indigo denim that has a similar shape and silhouette to the suit trousers, so they will look consistent with your tailored jackets. Remember to break them in properly.

14. Slim Neutral Corduroys

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Cords, preferable in a 5-pocket jean cut, are your casual alternative to the trousers for times when raw denim is a little too rugged. Look for a pair in a neutral earth tone like a dark British khaki or chocolate brown, like these.

15. Leather Dress Boots

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We’ve been talking about the value of these for a while now. If you don’t already have a solid leather dress boot, start with an oxblood wingtip style – like these – and your F/W wardrobe will be changed forever.

16. Rugged Casual Boots

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Sometimes the winter weather calls for something a little tougher than the leather dress boot. That’s when you break out the hardnose alpine boot. If you’re not into the alpine style, the classic bean boot is a reliable casual alternative, as is a rugged Red Wing.

17. Sleek Chukka Boots

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The dress boot is your formal option, the alpine is your casual go-to, and these are for everything in between. Look for a neutral brown or tan pair in a suave suede or a sleek leather if you live in a rainy/snowy climate. The popular Clarks desert boots are cool, but I like something with a sharper toe box and more structure to keep up with the lines of the suit and sport coat, like these.

18. Chunky Neutral Scarf

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When it comes to scarves, you only need one really nice piece of cashmere in a neutral color. Think thick, chunky, and soft. A beige or camel version will work with just about everything. If you’re pale skinned, consider going a little darker khaki, more toward chestnut.

19. Navy Patterned Tie

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Similar to a good scarf, a good tie will work with a number of shirts, sport coats, and suits. Look for one with a navy blue base and light blue/cream repeat pattern in a medium scale, like this one. It’s the most versatile, in my opinion. I have probably a hundred ties, but wear the one above weekly.

20. Brown Felt Fedora

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The hats that our grandfathers wore every day are now back, and with good reason. A brown or grey fedora with a medium sized brim, like this, is the perfect topper to a suited or smart casual look.

20 Pieces / 10 Outfits

To prove the versatility of a smartly curated wardrobe, here are 10 outfits, for 10 different occasions, using nothing but the 20 essential pieces listed above. Since all of the items are virtually interchangeable, you can make several more outfit variations as well.

1. Boardroom Ready

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2. Business Casual

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3. Weekend Tailoring

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4. Date Night

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5. Local Pub

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6. Fine Dining

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7. Casual Afternoon

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8. Cocktail Party

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9. Smart Casual


10. City Stroll

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Thanks, as always, for reading.

Yours in style,

Dan Trepanier


Photography by Alex Crawford. Styling by Dan Trepanier.

  • Tadyrall Jarrett

    Anyone know where to find Navy Tailored Overcoat?

  • Tadyrall Jarrett

    The Medium Grey Flannel Suit is hard to find.

  • bigdave323

    Some very good ideas, especially for casual wear. But, i must say, your approach to dressing is much more relaxed than mine. Brown boots with a grey suit in a business setting? Seriously? If I were your CEO, i would note in your file that you can’t be trusted to dress appropriately. Sorry. And jeans for upscale dining? Again, sorry, wwwwwaaaaayyyyy too casual. Upscale means upscale. Put on a suit, or at least a nice sportcoat and tie with tailored pants.
    I have noticed a trend, which seems to get worse over time, about how couples dress when out in an upscale or even casual date; the women dress up – nice dress, great makeup, good shoes, beautiful hair, nice jewelry, etc. The guy? Jeans, an open sportshirt, sneakers, messy hair, five-o’clock shadow, etc. I have even seen gorgeous women all decked out, with a guy who is dressed in a t-shirt and ragged shorts with boat shoes. What is wrong with men that they would disrespect a woman that way? And, what’s wrong with women who let them get away with it?

    • Ilya

      May I ask what industry and city do you work in? I’m asking because I can hardly imagine a corporation where wearing brown shoes with mid-gray (non charcoal) suit would put a stigma on you, unless it’s a very conservative menswear manufacturer. But maybe I’m doing it all wrong without even knowing that.

  • Sam Wilson

    What are those boots in #5, 7, 10? The imprint looks like Ugg but I can’t find anything similar online.

    I’m a newbie here (the clothes world) and really appreciate your site. One of the best I’ve found.

  • Ian

    Great post Dan, thank you!

    Anyone know of any current online options for the thick scarf mentioned above in a khaki/camel color? (I’m pale as hell!)

  • Branas

    Dan (or anyone else who can attest), do you find that well-made garments and footwear tend to be more comfortable on the body as you go about your day? Because looking at the textures and the way it drapes so smoothly and naturally, I would seriously imagine it does. Anyway, lots of inspiration to add to my list from here, thanks for the post as always!

    • TO

      Branas- certainly this is the case. Well-made garments, usually purely made of natural fabrics, breath well, usually are soft to the touch and tend to have a natural effect of conforming to the body over time better than more cheaply (less well) made items. Same goes with beautifully (well) made leather shoes. The latter I rarely see in the streets of Toronto (and it really stands out when I do!)– I think guys here are really missing out in that regard, even when they where a nice suit to work or casual outfit, they are missing a lot of style and comfort on their feet.

      • Oppi V

        Totally agree on the TO comment. And the availability of fine footwear reflects the market demand. I probably ranted about this at styleforum.

  • Tom

    Such a great post. Next level stuff!
    Might want to give that white oxford shirt a nice wash though. ;)

  • PeterBCunha

    Great post! Handy!

  • Harrison Krupnick

    I really like these essential pieces articles. They’re a great feature of AOS which I for one look forward to. I would suggest adding details about each piece (manufacture, etc.) like you do on the other posts.

  • chris

    What brand of peacoat is that?? The collar looks fantastic and I’ve never found one with a great collar.

    • Harrison Krupnick

      Look into Schott NYC’s peacoats. They have great collars and are very reasonably priced for the quality you’re getting.

      • chris


    • Phil

      It’s from Suitsupply

  • TO

    Great list. I like having a cropped peacoat, but I don’t wear tailored jackets on the regular. May I ask what brand is the chunky cashmere scarf, beautiful piece, and also the shawl cardigan? I must say the most annoying thing sometimes with shawl cardigans is when they don’t ‘keep’ their roll around the collar well- it really needs to be hefty to stay in place! For this reason I can’t layer under one that I have that’s pure linen. I am going to look for a more subdued-colour lace for my alpine boots like the ones here, I am getting sick of the red ones they had when I found ’em.

    • JBells

      The tag looks to be uniqlo

      • TO

        Ah yes I see now that you appear to be right. Thx!

  • PG

    Love this type of feature but a tweed vest is hardly an essential and most people shouldn’t be wearing any type of fedora, especially when down vests and toques are actually more functional. Being a stickler here but the forest green turtleneck looks like army green. And that brown leather is kind of hideous but personal taste. I know this seems like a lot of criticism but ‘essential’ is a strong word to use and usually you’re a little more on point. Rebrand is awesome in any case, keep up the great work.

  • AFH

    Yeah I’m not really feeling the mid-grey flannel DB as a separate, it really would need to be beefy to work. I think a single-breasted would work better.

    I also wouldn’t wear oxblood wingtip boots into a boardroom, but whatever.

    A lot of the looks are really ‘solid’ and ‘everyman’, which is by no means a bad thing, but there’s a lack of style & fun. Where’s the fair isle patterns? The groovy flannel shirt? It’s a long, cold winter and I need some colour.

    People who moan about denim being cold need to invest in some decent undergarments. Sartorialists who know get their winter trousers unlined as long-johns are implied.

  • cam

    very nice list AOS…i have to add a cashmere crewneck, down vest, knit cap, wool socks and some gloves to the mix…its cold outside of LA guys!!!

  • tommyjohn_45

    Great list, Dan. Happy to see that there are quite a few items on here that I have purchased throughout this season (you’re knowledge is rubbing off!). A 3/4 length coat is my next investment piece I am hoping for. With coats hitting the clearance racks, it’s the perfect time to buy. At first I was leaning towards a camel or black option, simply because I have a spring/summer navy peacoat…. Would you suggest still sticking with navy for the versatility?

    • cam

      not dan here of course but i have one in navy and one in charcoal and i find myself wearing the charcoal more. i wear a lot of navy (suit, cashmere sweaters etc) and find the charcoal to add more balance to my outfits. plus the charcoal is a great option for more formal events without going black (which i try to avoid wearing personally). just my 2 cents

      • tommyjohn_45

        Thanks Cam, appreciate the point of view. Haven’t thought about charcoal, but I’ll keep it in mind. Cheers

  • AdamE

    Pretty awesome list, and pretty good looks except for #8… Turtleneck over the white button down with the collar popped? I think that look would work if you either went just with the turtle neck under the blazer, or with the v-neck over the button down, under the blazer…?

    Otherwise the list is pretty solid. I can’t say I have all of these pieces, but the ones I do have get a ton of mileage mashed up in different combos. The value of the Cords cannot be overstated either. They are comfy like jeans, but have the big advantage that they don’t get cold the same way that denim does in winter…

  • Miguel

    One of the best features on AOS, 20 uotfit combo never fails.

  • Styles

    Hi dan – nice post. I wondered why you chose a grey mid-weight flannel suit as opposed to a navy, but I saw a lot of blue in the overcoat and pea coat. I suppose a db suit would be multifunctional but wouldn’t a single breasted suit be more so?

    • tommyjohn_45

      Dan also mentions a 4 season Navy suit in his Spring ‘top 20’ list as well.

  • JBells

    I absolutely love these types of posts.
    A knit shawl cardigan is one of my favourite pieces to wear!

    • tommyjohn_45

      Agreed, love throwing one on. My only issue is that they are so warm, I often have to take them off indoors.

      • JBells

        haha! yup i got the back sweats going on as I type

        • tommyjohn_45


    • AdamE

      The chunky knit shawl cardigan is the most underrated garment for football fans. If have a chunky double breasted knit cardigan, that I first bought precisely for tailgaiting at cold Bills games… I use it plenty in all sorts of contests, but it’s great on its own in the fall, or with a vest/coat for those late season games…

      Rather than a gawdy jersey and enough layers to look like the kid in The Christmas Story, often a t-shirt or polo, under the caridgan, and then a jacket over top gives you exactly what you need to stay warm, and to look good…