Cooler temps call for warmer footwear. However, you don’t have to sacrifice comfort and style. If you’re looking to up your shoe game this season, here are seven men’s shoes for fall and winter.
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Our profession and hobbies typically determine the style of footwear we purchase. For the first 25 years of my professional life, leather dress shoes, followed by Crocs and athletic shoes, dominated my foot-wearing life. Today, my footwear of choice centers around Hey Dude’s, court shoes for tennis and Pickleball, with Cole Haan drivers and Chelsea Boots bringing up the rear.
Most fashion-forward men, including myself, pay close attention to our shirts, pants, and outerwear, yet often need to improve when buying shoes. Several years ago, a professional maitre d’ told me that he always evaluates a man’s shoes before deciding if he’s allowed access to famous clubs and restaurants. That’s when I turned my attention to upping my “shoe-game.”
Here are my shoe recommendations for this Fall and Winter.
Cole Haan Broadway Cap Toe Oxford – $220
More formal business dress mandates a stylish shoe. These Cole Haan Oxford cap toe lace-ups are ideal.
Peter Millar Excursionist Venetian Loafer – $245
The Excursionist Venetian Loafer from Peter Millar easily dresses up or down.
Cole Haan ZEROGRAND Oxfords – $180
ZEROGRAND Oxford’s from Cole Haan combine comfort and fashion for work and play.
Allen Edmonds Denali Chelsea Boot – $299
Allen Edmond’s Denali Chelsea boot is a must-have for fall and winter.
What’s the difference between Chelsea and Chukka Boots?
Both Chelsea and Chukka boots appear similar. However, there are slight differences in design and style. For starters, Chelsea boots don’t have laces, are typically made from high-quality leathers, and are dressier. Chelsea boots gained popularity when the Beatles and The Rolling Stones wore them in the 1960s.
Also made famous by our English friends, Chukka boots gained noterity after World War II as British soldiers donned the style. Chukka boots have laces and a slightly lower ankle cut than Chelsea boots. Chelsea boots are dressier and more formal than Chukka boots. Owning a pair of each provides flexibly and style, which is important to me in all fashion purchases.
Johnston & Murphy Upton Chukka Boot – $165
The Upton Chukka Boot by Johnston & Murphy adds a new dimension to fall footwear.
On Cloud 5 Combo – $150
The On Cloud 5 Combo casual sneaker makes running weekend errands a breeze.
Adidas Stan Smith Originals – $100
Available in 25 color options, Stan Smith Originals stand fashion’s test of time.
The Stan Smith Original by Adidas remains a timeless classic tennis shoe.
Remember, you don’t have to sacrifice style or comfort while these seven men’s shoes for fall and winter. There are many others I like, so grab a few pair that make you look and feel your best.