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 sex-life, 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


Mid Gray Flannel Suit

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


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


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


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


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


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


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


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


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


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


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


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


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


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


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


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


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


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


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


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


2. Business Casual


3. Weekend Tailoring


4. Date Night


5. Local Pub


6. Fine Dining


7. Casual Afternoon


8. Cocktail Party


9. Smart Casual


10. City Stroll


Thanks, as always, for reading. 

Yours in style,

Dan Trepanier

Shop Custom Menswear Made in America


Take me to the Shop