5 Men’s Dress Shoes So Comfortable, They Actually Feel Like Sneakers

Dress shoes are a staple in any guy’s closet — and when it comes to quality, they should be just as comfortable as they are stylish. Whether you’re heading into countless meetings or back to back weddings this year, we’ve rounded up the best comfort-driven styles on the market. In fact, we’re even going so far as to say they’re comparable to your favorite pair of sneakers.

Below, shop styles from Clarks, Rockport and more.


Essential Details II Waterproof Wingtip

This stylish wingtip features a plush footbed that molds to your feet and truTECH technology to absorb shock in the heel. Bonus: it even features a waterproof leather upper and special seam sealant to keep your feet dry all season long.

Rockport Essential Details II Waterproof Wingtip
Rockport essential details II waterproof wingtip.
CREDIT: Zappos

Shepsky PT Oxford

Coming in at just under $90, this wallet-friendly pick won’t disappoint. An EVA insole offers all-day wearability, while a breathable cotton lining makes this pair anything but stuffy. On top of all that, it’s also slip-resistant.

Hush Puppies Shepsky PT Oxford
Hush Puppies Shepsky PT oxford.
CREDIT: Zappos

2.Zerogrand Laser Wing Oxford

A sneaker-oxford hybrid, the Cole Haan Zero Grand takes comfort to a whole new level in every part of its design. It’s made with the same kind of foam cushioning you’d expect from a running shoe, a perforated leather upper for easy movement, and Comfort Fitsock technology that instantly cradles to the shape of your foot without having to be broken in.

Cole Haan 2.Zerogrand Laser Wing Oxford
Cole Haan 2.Zerogrand laser wing oxford.
CREDIT: Zappos

ECCO Holton Apron Toe Slip-On

If you prefer a slip-on style, this option from ECCO is just for you. It features a breathable leather lining so your feet will never get too sweaty, as well as a removable insole and dual goring for an ultra-flexible fit.

ECCO Holton Apron Toe Slip-On
ECCO Holton apron toe slip-Oon.
CREDIT: Zappos

Clarks Gilman Mode

Perfect for more formal occasions, the Clarks Gilman Mode combines classic style with a luxurious feel underfoot via an Ortholite footbed. The shoe brand has been a leader in comfort since its finding in 1825, so you know this pair is destined to be a great investment.

Clarks Gilman Mode
Clarks Gilman Mode.
CREDIT: Zappos

Want More?

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