11 Best Men’s Shoes to Shop Now on Amazon for Under $150

It’s easier than you think to build a trend-driven shoe wardrobe today for under $150. A range of well-known men’s brands are doing their take on classic wingtip oxfords to Chelsea boots and penny mocs that won’t put you in the red.

What makes these looks wardrobe essentials is their style versatility as well as comfort features. Consider wearing an ankle boot with an office-appropriate suit, then team it with a pair of jeans for a casual night out. Comfort-wise, these styles feature flexible outsoles and cushioned footbeds for enhanced support, with many offering the same fit and feel as a pair of sneakers.

If you’re just launching your career and building an appropriate shoe wardrobe, or updating your current shoe closet, these looks are both affordable and fashionable.

Here, FN has put together a string of options that will take you year-round.

Rockport We Are Rockin Chranson Walking Shoe

This comfort-driven style features a natural rubber outsole for enhanced underfoot, while a mesh lining wicks moisture away from the foot for comfort. A proprietary TruFlex comfort system provides shock absorbing heel cushioning.

Rockport, we are rocking, walking shoes, mens
Rockport men's We Are Rocking shoes.
CREDIT: Amazon

Skechers Relaxed Fit Segment-Dorton Boot

A casual Chelsea ankle boot with comfortable side gores allows for easy access. The oiled leather upper offers a worn-in look and feel.

Skechers, segment-dorton boots
Skechers men's relaxed fit Segment-Dorton boots.
CREDIT: Amazon

Unlisted by Kenneth Cole Oxford

Keep it casual with a classic oxford set on a preppy-inspired red brick sole that works as the perfect complement to a casual suit or jeans.

Unlisted by Kenneth Cole , mens shoes
Unlisted by Kenneth Cole men's oxfords.
CREDIT: Amazon

Ferro Aldo Blaine Boot

This eco-friendly boot is made entirely of vegan materials. A hidden inside zipper is designed for easy access, while waxed add to the boot’s rugged causal styling.

Ferro Aldo Blaine , boots
Ferro Aldo Blaine boots.
CREDIT: Amazon

Steve Madden Fenta Sneaker

A lightweight fabric sneaker-inspired style is done in casual chambray and sports a white rubber sole.

Steve Madden, fenta, sneakers
Steve Madden men's Fenta sneakers.
CREDIT: Amazon

Clarks Tilden Way Penny Loafer

A classic penny moc takes inspiration from the ’50s, then modernizes the look with a flexible rubber outsole for comfort and Ortholite cushioned insole.

Clarks penny loafers
Clarks penny loafers.
CREDIT: Amazon

Timberland Logan Bay Chelsea Boot

A classic Chelsea boot features an anti-fatigue removable footbed for out-of-the-box comfort, while a rubber outsole offers traction on slippery surfaces.

Timberland Logan Bay Chelsea boots
Timberland Logan Bay Chelsea boots.
CREDIT: Amazon

Skechers Sport Rig Mountain Top Sneaker

This easy to wear style is hands-free leaving laces behind. Its rugged outsole makes it an ideal travel shoe, transitioning from a walk in the city to a day of light hiking.

Skechers Sport Rig Mountain Top Sneaker
Skechers Sport Rig Mountain Top Sneaker
CREDIT: Amazon

Crocs Santa Cruz Loafer

A casual slip-on style does double duty as a slipper or shoe, made of lightweight canvas with a durable sole.

Crocs, mens loafers, santa cruz
Crocs men's Santa Cruz loafers.
CREDIT: Amazon

Clarks Stinson Hi Chukka Boot

This soft suede chukka is set on a sneaker-like rubber platform for a laidback touch.

Clarks, chukkas
Clarks chukka boots.
CREDIT: Amazon

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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