Written by

Chris Gonzales


Martin Miranda

Cold weather may already be upon us, it’s not too late to spruce up your winter wardrobe a bit. Here are a few basic items to help you out.

Note: Nothing in this guide will surprise anyone who follows fashion trends and has already developed their own distinct personal style. We’re not being that fancy today. This guide is for those whose fashion sense typically ends at sneakers, jeans, and a hoodie. The idea here is that a few simple items, combined in the right ways, can make all the difference.

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Old Navy's slim-fit chambray shirt. ($35)

Old Navy’s slim-fit chambray shirt. ($35)

Old Navy Chambray Shirt »

A chambray shirt (or two) is a great place to start when upgrading one’s wardrobe. It’s a lighter and softer fabric than denim, so it’s perfect for layering under a sweater or coat in the winter, and then works nicely on its own when warmer weather rolls around.

If you’re going to get two of these shirts, we recommend getting a red and a mid-tone (blue/gray) one. From there, you can easily mix-and-match with most other wardrobe pieces.

J.Crew's forest fair isle sweater ($80)

J.Crew’s forest fair isle sweater ($80)

J.Crew Fair Isle Sweater »

While fair isle sweaters are often confused with ugly Christmas sweaters (and there can indeed be some overlap), the right one can make a great, classy addition to your wardrobe. J.Crew’s forest fair isle sweater is the sort of thing I’m talking about, with its calm earth tones and a pattern that won’t make everyone’s eyes bleed.

If you’re too timid to spring for a fair isle, you can always shop for sweaters or cardigans in these colors during the winter and be just fine:

  • Camel/brown
  • Navy
  • Gray/mid-tone
  • Dark green (wear a red plaid shirt underneath, or maybe a light button-up oxford + jeans + brown shoes + brown belt)
  • Cream
  • Red (pairs well with olive chinos)

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Alpha Industries' N-3B slim-fit parka. ($121–$200)

Alpha Industries’ N-3B slim-fit parka. ($121–$200)

Alpha Industries N-3B Slim-Fit Parka »

If winters where you live tend toward the extremely cold, Alpha Industries’ N-3B slim-fit parka is a fantastic choice. It will keep you warm and dry in freezing weather, in some cases even if you’re only wearing a t-shirt underneath.

Schott's classic 32oz. wool pea coat. ($280–$350)

Schott’s classic 32oz. wool pea coat. ($280–$350)

Schott Classic 32oz. Melton Wool Pea Coat »

A quality pea coat is one of the finer investments you will ever make. This one by Schott will keep you very warm and dry even in harsh conditions, and you’ll look awesome all the while. Comes in a handful of colors but navy is usually the best choice.

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UNIQLO's flat-front chinos. ($40)

UNIQLO’s flat-front chinos. ($40)

UNIQLO Flat-Front Chinos »

While there’s nothing wrong with a good pair of jeans, they can get boring after a while. Get yourself some chinos like these flat-front ones from UNIQLO and instantly add a touch of class to your outfit. The best part is that you don’t have to stick with boring colors like tan and dark brown (although those can be fine too) — you can rock chinos in olive, red, navy, forest green, etc and not look weird if you do it right.

For extra winter comfort, you might consider a pair or two of corduroy pants. Same color principles apply.

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Wolverine's 1000-mile cap-toe Rockford boots. ($299–$399)

Wolverine’s 1000-mile cap-toe Rockford boots. ($299–$399)

Wolverine 1000 Mile Men’s Rockford Cap Toe Boots »

If you’re used to buying cheap sneakers, the price tag on these boots may stun you a little (even though they’re on the lower end of the leather boot spectrum). But, you get what you pay for — not only do they look awesome, they’re also comfy without too much break-in needed. They fit quite large though, so order a size down.

Wigwam's merino wool hiker socks. (Prices vary with color and size, but most pairs run about $10–$12 a pop)

Wigwam’s merino wool hiker socks. (Prices vary with color and size, but most pairs run about $10–$12 a pop)

Wigwam Merino Wool Hiker Socks »

Don’t neglect to keep your feet warm when cold weather hits. Get some of these crew-length merino wool socks and your feet will thank you. They’re warmer than basic cotton socks without adding much bulk, and they breathe nicely enough that you can keep wearing them in spring.

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Stheart's “fire” variable beanie. ($20)

Stheart’s “fire” variable beanie. ($20)

Stheart “Fire” Variable Beanie »

If you’re looking for something to keep your head warm, Stheart makes some great beanies. A favorite of ours is the “Fire” variable beanie, which can be worn either slouched or cuffed. Either way you wear it, that bright red color looks great and adds some flare (get it?) to your winter outfit.

La Matera's Diplomático wallet. ($150)

La Matera’s Diplomático wallet. ($150)

La Matera Diplomático Wallet »

The Diplomático wallet by La Matera manages to be both casual and sophisticated. It’s handcrafted from Italian calfskin leather and geometric-patterned Argentine woven fabric, with six card slots and a larger cash slot within.

It pairs nicely with the company’s own navy San Martín watch.