Hero image

2021 Fall + Winter Men’s Footwear Guide


There’s no stopping it; we’re heading right into the cold heart of the year. As the days get shorter and cooler, with more reasons to wear long sleeve henleys, hoodies, and pullovers, it could be tempting to let your footwear game slip a notch or three. Don’t forgo fashion just because conditions outside are a bit tricker than usual. With a little prep work, some smart buys, and proper footwear care, you can stay stylish until spring!

Trends To Watch Out For In 2021

These trends are easy to incorporate into your wardrobe (assuming it's filled with Fresh Clean Tees, of course). They’re timeless and thus easily able to carry you from late fall to early spring. A few high-quality footwear items can keep you looking sharp, whether you’re on your way to the office or out at the local pub for a few pints.

Chelsea Boots

Chelsea boots can keep your feet warm, even in supremely bad weather, and they look much more stylish than those clunky winter boots you probably have lying around your closet (or garage). Chelsea boots don’t offer you as much coverage above the ankle, so they’re not great for trekking through feet of snow, but they’ll do just fine on slushy, snowy city streets.

Chelsea boots are a slightly edgier and fashion-forward form of ankle boots. These low-heeled, round-toed boots come with a characteristic strip of fabric or elastic on the side. You pull them on rather than lace them up. Although more traditional variations of the Chelsea boot have matching elastic or fabric strips, you can get them in more vibrant colors.

There are plenty of high-quality brands like New Republic that sell sophisticated, serviceable Chelsea boots for under $100.

Retro Sneakers

Just because the mercury’s dropping doesn’t mean you have to put away your sneakers. Retro sneakers add a punch of personality and style to your outfits, and, when done right, they can be downright iconic, even in colder weather. You’ll see a lot of retro-inspired sneakers in bright colors this winter. However, if deeply hued oranges or greens aren’t for you, you can always opt for more neutral tones. Just remember that comfort beats out everything else when it comes to sneakers. The golden rule is that you won't look cool or chic if you’re not comfortable wearing them.

Find old-school kicks that work with your existing pieces. Classic Reeboks go well with a preppy, buttoned-up wardrobe, whereas Chuck Taylors from Converse can work well with edgier business casual looks. Don’t try to fit a round peg into a square hole; there’s a retro look that will work with what you have already, guaranteed.

Don’t make the mistake of thinking that because sneakers are casual, you don’t have to take care of them like you would dress shoes. Keep your kicks clean, especially if they’re in a lighter color.

Oxford Shoes

Oxford shoes are one of the most versatile dress shoes you can invest in. Leather oxfords offer full coverage on the tops and sides of your feet, and they can elevate even the humblest pair of jeans. They look spectacular with suits too. Invest in a good pair of oxfords and you’ll find that as you break them in, they’ll get just as comfortable as your most beloved sneakers.

Featured: White Crew Neck Tee

Chill-Friendly Materials Built To Last

All things considered, leather can prove the best material for autumn and winter footwear. Properly treated leather can withstand nearly all conditions and come out looking pristine. Stay away from suede, however, as well as other porous materials that can all too easily absorb moisture. Insulation is important too, and rubberized soles will keep you from wiping out on slick sidewalks.

Weatherproofing Like A Pro

Whether you’re an Oxford man, a Chelsea boot guy, or a retro sneaker dude, weatherproofing your footwear is vital. Do some prep work, and you’ll keep your shoes looking incredible for many seasons to come.

Water is the sworn enemy of leather shoes, causing the material to warp and sometimes even crack. Polish your shoes with a wax-based solution, such as Kiwi. For under ten bucks, you can prolong the lifespan of your footwear and simultaneously get them gleaming.

Always remove your shoelaces before polishing, though, and let your shoes dry thoroughly before wearing them again. Although waxes and polishes can repel water and salt, there’s a good chance that you’ll come home from a particularly wintery day with a salty crust on your shoes. When that happens, it’s essential to get the salt off right away, as it can destroy the leather. Wipe your shoes down with a damp cloth and later remove any lingering stains with a simple DIY water and vinegar solution.

So there you have it, everything you need to know to stay warm and stylish this fall and winter.

— Elizabeth Lavis

Cart 0 Items

Your cart is
currently empty

Not sure where to start?

Shop Best Sellers

Save $7.95 on this order

plus 20% off & FREE shipping on all future orders by joining our membership program for $19/yr