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When it comes to winter footwear, most of us (understandably) default to snow boots and duck boots to protect us from the elements. But we’d argue that for more formal occasions (like heading to the office or date night), you should swap in a pair of handsome dress boots. The best ones have a solid construction, luxe (usually leather) materials, so you can wear them with a suit, and they can get you through sleet and snow with ease.
Plus, nothing beats opening the box containing your brand new soles, smelling the leather, and feeling the workmanship. Seriously, it’s intoxicating.
New to dress shoes? start with a classic chukka or Chelsea boot–in either black or brown. Also, keep weather top of mind; a waterproof style will be more practical for rainier cities than, say, suede. Just be sure to keep this list on hand as you expand as you shop, so you can upgrade your style game and breathe life into your closet to boot.
Read more: Best Winter Boots for Men
Thursday Boot Company Men’s Captain Cap Toe Leather Boots
They say that fine wine gets better with age. The same can be said for a great leather boot. Available in 11 colors and made with 100% leather, you will want to keep the Captain lace-up boot within arms reach for years to come.
Gucci Men’s Lace-up Ankle Boot
Just like their horsebit loafers, Gucci’s ankle boots are gorgeous and made to last a lifetime. They also make for great luxury gifts for men.
Magnanni Pierce Plain Toe Boot
This handsome design from Spanish shoemaker Magnanni will instantly upgrade your daytime outfit with rich, pebbled leather and a streamlined plain toe, while a cushioned, arch-support footbed offers all-day comfort. Consider pairing with your favorite dark wash jeans and a sweater for a foolproof winter look.
Read more: Best Shoes for Men
Taft Clothing “The Livingston” Boot
If you think that wool is just for cozy sweaters, think again. The Livingston Boot by Taft is made with winter-ready printed wool and a sharp Spanish leather wingtip accent. Plus if you wear down the sole (and we wouldn’t be surprised) the Blake-stitched constructions means you can easily replace them.
Coach Metropolitan Chelsea Boot
A pair of well-made black Chelsea dress boots can be a foundational part of your evening wardrobe. Coach’s design features smooth leather, a comfortable rubber sole, and a pull tab for on-and-off ease.
Cole Haan OriginalGrand Chukka Boots
If you are looking to elevate your footwear game but aren’t ready to commit to a full-on dress boot, the newly re-designed OriginalGrand Chukka boot Cole Haan might be a great start. The elegant leather upper is expertly balanced with a sporty, ribbed midsole, offering a casual start to your dress boot journey.
Saint Laurent Men’s Wyatt 40 Harness Biker Boots
Saint Laurent practically invented the Western-meets-luxury boot category and honestly, we aren’t mad about it. If you want to earn some serious style points, and add an inch at the same time, slip into the Wyatt 40 style with soft almond toe, rich calf leather, and ankle harness.
Clarks Men’s Bushacre 2
Known for their durability and versatility, owning a pair of suede Clark Chukka Boots should be a no brainer. Available in a variety of colors, have fun mix-and-matching with your casual office looks or pack a more neutral color (white or taupe) on your next vacation.
Mr. P. Andrew Split-Toe Shearling-Lined Suede Chukka Boots
Suede boots might be considered the more casual alternative to leather, but when styled correctly, they can still elevate your outfit. Opt for a darker brown color to start (for greater versatility) like this design from Mr. P that features a split-toe, Vibram leather soles, and recycled materials.
UGG Kirkson Boot
If you live somewhere that frequently rains or snows, your boot wear might need additional protection. Check out this winter-ready UGG design made with waterproof leather, a wool blend lining for warmth, and a molded rubber Vibram outsole for enhanced traction.
Hugo Boss Side-zip ankle boots
Like a pair of classic jeans, the ankle boot is one of those tried-and-true footwear staples that never go out of style. This sleek and contemporary design by Hugo Boss is available in a rich black or brown hue with an easy-to-wear side zipper.
Beckett Simonon Elliot Balmoral Boots
Characterized by a single line of stitching and broguing along the toe, Balmoral Boots were originally made for England’s royal family. Nowadays, they carry style cred for us commoners like this version from Beckett Simonon made with full-grain calfskin leather that only gets more stunning with age.
Andrew is a freelance writer, fashion columnist, and editorial stylist covering fashion, commerce, skincare, grooming, and health.
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