The 5 Best Men’s Shoes Millennials Will Actually Want to Wear This Fall/Winter

By Riley Jones
Riley Jones

Riley Jones

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Gucci Strand Chelsea Boot
Gucci Strand Chelsea Boot
CREDIT: Gucci

Let’s face it: Millennials can be pretty finicky when it comes to fashion. For younger demographics, traditional men’s footwear isn’t always the most enticing category, but there are certain staples and styles that are sure to appeal to the 20-something-and-under guys in your life.

Whether it’s an updated take on a classic like the Chelsea boot or an iconic workwear look, you’ll find something for everyone’s taste below.

Wolverine Cordovan 1000 Mile Boot
A tried and tested staple, the https://footwearnews.com/t/wolverine/"; id="auto-tag_wolverine" data-tag="wolverine" >Wolverine 1000 Mile Boot isn’t just a shoe, it’s a wardrobe investment. The American-made leather https://footwearnews.com/t/boots/"; id="auto-tag_boots" data-tag="boots" >boots can be worn year-round with just about anything in your closet.
CREDIT: Neiman Marcus

Wolverine Cordovan 1000 Mile Boot, $360; neimanmarcus.com

Amiri Suede Ankle Boots
On-trend designer Mike Amiri’s Suede Ankle Boots are designed intentionally wrinkled for a disheveled high-end look.
CREDIT: Barneys

Amiri Suede Ankle Boots, $995; barneys.com

Red Wing Roughneck Boot
For those seeking something a bit more rugged, https://footwearnews.com/t/red-wing/"; id="auto-tag_red-wing" data-tag="red-wing" >Red Wing‘s Roughneck Boot is ready for everything from heavy-duty work to hiking.
CREDIT: Nordstrom

Red Wing Roughneck Boot, $270; nordstrom.com

Gucci Strand Chelsea Boot
If you’re looking for a Chelsea boot that will stand out from the rest, https://footwearnews.com/t/gucci/"; id="auto-tag_gucci" data-tag="gucci" >Gucci has you covered with this model, which features the brand’s iconic red and green colors and an embroidered golden bee.
CREDIT: Nordstrom

Gucci Strand Chelsea Boot, $895; nordstrom.com

Givenchy Leather Combat Boot
For an even edgier take on the traditional combat boot, consider https://footwearnews.com/t/givenchy-2/"; id="auto-tag_givenchy-2" data-tag="givenchy-2" >Givenchy‘s Italian-made black leather interpretation.
CREDIT: Barneys

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Givenchy Leather Combat Boots, $995; barneys.com

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