15 Most Comfortable Loafers 2023, Tested & Reviewed

“My loafers resemble a classic men’s penny loafer, but they really fit and feel like a slipper,” Haller says. Each insider-favorite pair is crafted at an Italian atelier using a sachetto construction, the key to a glovelike fit and buttery feel. “They mold to your foot with wear—the shape of the leather becomes your foot which offers comfort and support.” Comfort-first adjustments Haller has made include removing the toe box interlining and heel box, which contributes to the slipperlike vibe, and finishing each shoe with a lightly padded insole.

It’s hard to choose just one style to highlight, but I have to shout out the vintage-feeling colorblock pairs. I can envision them with so many great fall outfits, from neutral sweater sets and denim to printed autumn midi dresses and tights.

Sizes: 36–41

Colors: Brown/bone, black/bone

G.H. Bass’s Weejun loafer has been a staple for decades. Fashion insiders and everyday shoppers come back to it time and time again for its classic, flat-strap design and easy-to-break-in construction.

Sizes: 5–11

Colors: Black, burgundy, cognac

Heel height: 0.87″

What reviewers are saying:…