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Don’t sacrifice style with winter boots: The key to functional fashion this season

Stay stylish even in mens winter dress boots

Closeup of man's feet wearing insulated winter boots in the snow.
Unsplash

The weather is beginning to make your trip to the office or the grocery store much more precarious. The snow is falling, and the roads are getting wet and slippery. That is when it becomes imperative that you get the right garments and shoes to protect yourself against the elements. The only problem? They are rarely as stylish as the rest of your wardrobe. Winter boots specifically have a hard time retaining the style of other seasons, and men’s winter dress boots are the closest you will get to style while staying elevated. That is why you need to find the perfect outfit to stay warm and dry while not sacrificing your style. How do you do that? By mastering functional fashion. Here is the way to nail this look.

Why winter boots feel less stylish

Man in chinos with boots
Maksim Goncharenok / Pexels

Really, what this comes down to is the argument of function over fashion. When you have something that looks great, it is often constructed without focusing on making your life easier. When you have something made for a specific purpose, you often sacrifice the look of the boot because it is meant to keep your feet warm, dry, or both. Keeping your style elevated during the winter months will come down to finding a pair of boots that find the balance between the two. Functional fashion is the hallmark of a great winter boot look.

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What boots to grab for the stylish function: Nicks Boots Insulated Waterwork

Nicks Boots Insulated Waterwork
Nick's Boots

When looking for a great combination of style and function, investing in something that has a healthy mix of both is important. Sometimes, that comes at a higher price than other boots with one or the other. One of the best investments you will ever make will be with a pair of Nicks Boots Insulated Waterwork. Not only are they strong enough and functional enough to be worn by wildfire firefighters, park rangers, and other professionals, but they are stylish enough not to put a damper on your winter looks.

Specs
360º Stitchdown Welt for added water resistance
Vibram Unit Lug Sole
Water-resistant 7-8oz leather upper
Removeable full leather insole
Best-in-class thermal insulation

How to wear them stylishly

man wearing boots on street
Afif Ramdhasuma/Unsplash / Unsplash

As you might imagine, once you find yourself a pair of great winter boots that perfectly balance function and fashion, you will want to find a handful of products that do the same throughout the rest of your outfit. Keeping every aspect of your look on that line between function and fashion is a great way to stay warm and dry in the winter while not losing that ever-important edge of style. Here are the options to make a great outfit that will look great in the office or on a casual outing all winter.

The pants: Free Fly Anchor Chino Pant

Free Fly Anchor Chino Pant
Free Fly Apparel

When looking for that perfect functionally fashionable piece, the key is finding garments that look amazing and can be worn to get things done. The Free Fly Anchor Chino is one of the best pairs of versatile pants you will find. They look elevated enough for the office but with just enough stretch and a lived-in feel to allow you to brave the winter weather and even climb a snow mound or two.

Specs
Brushed fabric delivers a soft, lived-in feel
2-way stretch for awesome mobility
Casual, everyday style upgraded with performance benefits
Fixed waist with belt loops
Button closure with zipper fly
Back drop-in pockets for stashing phone, wallet, or keys

The shirt: Buck Mason Tavern Shepherd Check Pacific Twill

Buck Mason Tavern Shepherd Check Pacific Twill
Buck Mason

Getting the right shirt comes down to the aesthetic you want to go with. If you are looking for something perfect for a day in town or watching the snowfall on the back porch, a great sweater is the way to go. However, if you need something just as workable for a day at the office, you need a good flannel button-up. Buck Mason is one of the best functional fashion houses on the market, and this check is subtle and versatile, perfect for a casual day on the town or a shift in the office.

Specs
4-oz yarn-dyed cotton
single rounded chest pocket
shell buttons
washed for lived-in feel

The jacket: Taylor Stitch Evans Blazer in Forest Birds

Taylor Stitch Evans Blazer in Forest Birds
Taylor Stitch

We know what you’re thinking: the above is a pretty casual outfit that may not be great for the office. That is where this bad boy comes in. The Evans Blazer is elevated enough to take the above ensemble from good to great and casual enough to stay in line with the rest of the aesthetic. Keep the collar down for an elevated look if you are in the office. If you are outside, flip the collar up to guard against the cold.

Specs
12-oz. 78% wool, 16% polyester, 6% nylon.
Unlined
Notch collar
Single chest pocket
Two lower patch pockets with open tops
Hand wash cold and lay flat to dry

There you have it—a great outfit to wear this winter when you need to bridge the gap between functional protection against the cold and wet and an elevated look to retain style. Use this framework to wear those winter boots, and never sacrifice your style.

Mark D McKee
Mark is a full-time freelance writer and men's coach. He spent time as a style consultant and bespoke suit salesman before…
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