Thinking about updating your footwear wardrobe and don’t know where to start? It’s easier than you think to build a trend-right shoe wardrobe that won’t break the bank — and you won’t even have to leave the comfort of your couch to shop for men’s shoes under $150 from Zappos.
Start with a pair of Chelsea boots, a fashion essential that goes from dress with a slim suit to casual with a pair of distressed jeans. They never go out of style, which makes them the ultimate investment piece.
Or consider a classic dress shoe, even if your office is casual Monday through Friday. You never know when that business meeting might come up unexpectedly or a wedding invitation might arrive from that cousin you never knew you had. A classic cap-toe or double monk strap are must-haves for suit dressing.
Since casualwear is now everyday wear, pick up a pair of Dr. Martens boots and Birkenstock clogs, iconic looks that you can wear year-round. And don’t forget a cozy pair of slippers with indoor-outdoor soles.
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Carlos by Carlos Santana Mantra Chelsea Boot
Classic Chelsea boots are anything but, especially when they’re given a mod spin with novelty red side gores, outsole and heel trim.
Rockport Classic Loafer Lite Penny
The penny moc is revisited in a comfort-driven version that incorporates a cushioned footbed, then picks up a flexible unit bottom.
Johnston & Murphy Tabor Dress Cap Toe Oxford
Every wardrobe needs a cap-toe oxford to finish off a tailored look, whether heading to the office or an after-hours event.
Florsheim Montinaro Double Monk Strap
The monk strap is revisited here in a double-buckle version, a trend-driven way to update a dress shoe staple.
Mark Nason Neo Casual
This chukka boot marries comfort with tradition in a classic silhouette that incorporates a bold wedge sole for some underfoot bounce.
Dr. Martens Tipton Robson II
This iconic British brand continues to be a go-to for comfort and style, with its cushioned SoftWair memory foam footbed and GripWair sole for traction on slippery surfaces.
Caterpillar Stiction Hiker Waterproof Ice+
The Vibram Arctic Grip outsole offers enhanced grip on slippery surfaces, while a removable footbed with microfiber lining provides supportive underfoot comfort. An added feature is a Thermochromatic lug bottom design that senses when temperatures drop to under freezing; it turns blue when it senses ice nearby.
Birkenstock Boston Oiled Leather Clog
A festival must-have, this comfort-driven style looks even better with a pair of chunky socks, taking the look year-round.
Old Friend Camouflage Moccasin
The camo trend continues, this time in an easy-to-wear indoor-outdoor version lined in cozy shearling.
Ugg Chester Driving Moc
This suede driving moc features interchangeable insoles — a cozy wool or leather-lined version — making them good to go from spring to winter.
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All products featured have been independently selected and curated by our editorial team. If you buy something through the links included on our site, FN may earn a commission.
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