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.
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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