7 Pairs of Shoes That Are Both Comfortable and Stylish

Beauty is pain? Not when it comes to a new generation of gorgeous, comfortable shoes that look just as good as they feel. Your footsies won’t be suffering the brunt of a shoe that does your sole no favors with these comfy pairs that don’t sacrifice good style and still pack plenty of panache.

1. Naturalizer Kaneli Heels

gorgeous comfortable shoes

Naturalizer Kaneli Heels | Naturalizer

We know what you’re thinking — Naturalizer, no thanks. But, this comfort label brand that may have been stigmatized in some circles has stepped up its fashion game yielding such soles as the Naturalizer Kaneli heels. Yes, it has that signature N5 Comfort technology, featuring a flexible sole, lightweight materials, extra cushioning, heel-to-toe balance, and a breathable lining. But, what we really love is the feminine look that gets a hint of tailored sophistication — not to mention this rich cordovan color.

2. Aerosoles Fortunate Shootie

gorgeous comfortable shoes

Aerosoles Fortunate Shootie | Aerosoles

Another “comfort” brand with a questionable fashion reputation, Aerosoles has likewise risen to the occasion. They are proffering one of the season’s most coveted shoe silhouettes: the shootie. It’s a hybrid heel and bootie, and it’s plenty chic. Try the Fortunate on for size. The femininely ruched shootie features a trendy front zipper and covered tassel. And, of course, comfort abounds thanks to the brand’s Heel Rest technology that also includes a memory foam foot bed, 3-inch covered heel, and an almond-shaped toe.

3.Yosi Samra Vienna Capri Leather

gorgeous comfortable shoes, flats

Yosi Samra Vienna flats | Yosi Samra

Purveyor of the original foldable ballet flat, Yosi Samra knows all about both comfort and beauty. While there’s a footwear wonderland of styles from which to select, one of fall’s favorites is the new pointed toe Vienna that goes from day into night in a flash. The refined pointed toe adds a sense of sleek sophistication while the tumbled leather and soft elastic topline make for a comfortable and secure fit. These flats even feature the brand’s new memory foam foot bed and rubber sole for additional comfort and support.

4. Stuart Weitzman Highstreet Over-the-Knee Boot

gorgeous comfortable shoes, boots

Stuart Weitzman boots | Nordstrom

These Stuart Weitzman Highstreet over the knee boots look like leggings as they’re constructed of swanky stretch suede, which is to say they’re quite warm and comfy — especially with an angled block heel for extra support. A slightly sharper toe adds a beautiful mod-yet-minimalist feel. Plus, the rich grey hue is this season’s version of black, meaning it’s on-trend and suitable for every occasion.

5. Kork-Ease Bette 2.0 Sandals

gorgeous comfortable shoes, sandals

Kork-Ease Bette 2.0 Sandals | Kork-Ease

A timeless ankle strap updated with a double textured wedge is the order of the day with the Kork-Ease Bette 2.0 sandals, which are offered in a patent variation or a full-grain leather with cork-look wedge. The Kork-Ease 2.0 Comfort Technology is a dual-density foam insole innovation that delivers support and comfort through outer foam that provides shape and support and inner foam that cradles the foot for cushioning in the strike zones.

6. Marni One Band Sandal in Techno Fabric

gorgeous comfortable shoes

Marni One Band Sandal in Techno Fabric | Marni

You might not normally equate high-fashion label Marni with the epitome of comfortable shoes. Yet the One Band Sandal goes against the fashion-is-pain mantra with a chunky, supportive heel, a rubber heel layer, and technical fabric with Velcro straps that is surprisingly flexible and forgiving for long days. And, who can deny their quirky, color-blocked edge? Not us.

7. Everlane The Modern Loafer

gorgeous comfortable shoes, loafers

Everlane The Modern Loafer | Everlane

High-gloss and high on style, Everlane’s The Modern Loafer is elegance defined with stitching details over the toe and a stacked leather heel with contrast rubber accent for durability. Made in Italy, these shoes are also high on quality. And even if the shoes are a bit rigid for the first few wears, they gradually mold to your foot for the peak of comfort.