The days are getting shorter and temperatures are dropping. Before we know it winter is at our doorstep.

While I would love nothing more than to wear a pair of sockless loafers year round, the truth is winter has other plans for how I cover my feet. It’s the season of handsome looks that can only come from dapper leather boots and sleek rubber dress soles.

If you’re looking for new key winter footwear pieces or to replace some worn out-of-style boots, this guide is going to help you survive the next winter in style.

The Styles

Pictured: Wolverine 1000 Mile Boots & Thursday Boot Co. Captain Boots

Lace-Up Boots

Lace-up boots are a timeless menswear item that should have a place in every man’s closet. A good lace-up boot will end right above the ankle and taper nicely to the foot for a sleek yet masculine look.

These boots pair best with casual denim for a rugged look in the fall and winter. Although casual in nature, lace-up boots can also be dressed up for a smart look with slacks and a button up shirt.

The best lace-up boots are made with high quality leather and feature a welted construction. When shopping for your first pair of lace-up boots always keep it simple with black or brown leathers. If you live in an area that gets some snow and ice than make sure to choose a lace-up boot with lugged soles for traction.

Pictured: Timberland Chillberg Waterproof Boots & Sorel Caribou Snow Boots

Snow Boots

There is a big difference between boots made to look good on a night out and boots meant to tackle snow and slush. Sadly, some guys don’t know the difference.

Every guy should have a pair of boots made especially to tackle harsh winter weather. Unlike some of the other footwear options on this list, your snow boots should be rugged and practical.

Unlike your lace-up boots, snow boots are going to be bigger, chunkier and heavier. The key to pulling off chunky snow boots in the winter is to balance out your silhouette with a chunky coat. This prevents you from looking too “bottom heavy” and prevents the clown shoe look. And to keep your snow boots looking fresh make sure to apply a round of leather boot oil before the beginning of the season.

Pictured: Allen Edmonds Fifth Avenue Cap-Toe Oxford

Oxfords with Dainite soles

Let’s be honest, business doesn’t end at the sight of the first snowfall. Whether it’s suiting up for the office or meeting a client for lunch, we are going to have to look our best regardless of the weather outside. This is where oxfords shoes with Dainite soles come in.

Normally an oxford dress shoe will have slick leather outsoles that are terrible in cold wet weather. Leather soles have absolutely no traction and your outsoles will be ruined after one too many wears in wet weather.

By opting-in for oxford shoes with rubber Dainite soles you can wear a nice pair of oxfords with a suit without worrying about slipping and sliding on icy pavement during your morning commute.

Pictured: Thursday Boot Co. Duke Boots & Loake Chatsworth Boots

Chelsea Boots

The chelsea boot is for the guy who wants to look sleek, polished and masculine. Made popular in 1960’s British mod scene, chelsea boots have managed to remain in-style thanks to it’s smart and versatile design.

Chelsea boots are great for cold weather wear because of their laceless design that can be dressed up or down. And since they are boots, you can wear them even when the weather gets crummy.

The best chelsea boots fit close to the foot and ankle for a sleek look. Since chelsea boots taper around the ankle you are going to want to pair chelsea boots with slim fit denim or pants. You can even pair chelsea boots with your favorite navy suit for an edgier look at the office.

Pictured: Church’s Ledstom Shoes & Allen Edmonds St John’s Double Monk Strap

Monk Strap Shoes

If you are ready to elevate your style to the next level than monk strap shoes are just the ticket.

A monk strap shoe resembles an ordinary oxford except that it replaces the laces with straps and buckles.

This style of shoe can add a touch of class to a casual weekend outfit or add some edginess to an otherwise boring suit. The possibilities are endless.

Monk strap shoes can be worn year round but they look especially good when paired with socks and trousers in the fall and winter. The key to making monk strap shoes work in colder weather includes making sure that the outsoles are winter appropriate. You are going to want to have rubber outsoles with a bit of traction. And to make sure your monk strap shoes match your winter palette, stick to black, dark brown or oxblood leather.

Pictured: Yeezy Season 6 Rat Boots & Nike Air Force 1 Duckboot

Sneaker Boots

Sneaker boots take the trendiest elements of a sneaker and combine them with the ruggedness of a boot. Perfect for winter weather, sneakers boots allow you to look great in casual outfits without worrying about rain, sleet or snow.

What constitutes as a sneaker boot exactly? Look out for the silhouette of a high top sneaker but with a chunkier sole and some insulation and padding for warmth. Sneaker boots are also usually made with waterproof materials which makes them perfect for walks in the city slush.

Out of all the winter footwear on this list, sneaker boots are definitely the most casual. These shoes follow trends a lot closer than other winter shoes. So if your style leans more towards trendy streetwear than this is the winter shoe to have.

Quick Tips: How to Choose the Best Winter Footwear

Now that you know the styles it’s time to cover what you need to keep in mind when choosing your winter footwear.

Accommodate Your Socks

One of the easiest ways to combat cold feet is to put on a thick pair of wool socks.

Unfortunately, not a lot of guys take this into consideration when purchasing a new pair of winter boots.

When trying on a new pair of shoes or boots make sure to leave enough room for the thickness of the socks you will be wearing when it’s freezing out. You’ll often find that you will need to size up to accommodate your socks.

Pick Shoes With Winter Soles

If you live in an area where there is a lot of snow and ice during the winter months then minding your soles is a must. Dress shoes with leather soles will get destroyed in wet weather.

Instead, make sure your outsoles are made out of rubber or have rubber attached to the leather sole as an extra protective layer.

For winter boots and casual shoes, going with thicker soles that are lugged will be a godsend when it’s miserable outside. This is especially true for those of you who do a lot of walking.

Be Mindful of the Materials

Not all shoe materials are great for winter weather. For example, if you love your pocketbook you should really avoid wearing fine suede when it’s wet outside. This means no suede chelsea boots after it has snowed three feet. Suede gets absolutely ruined when repeatedly wet.

Instead, you are going to want to choose boots and shoes that are made of leather, rubber or even a water resistant nubuck. These materials won’t get ruined if it snows and will still look great on your feet.


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