Cole Haan’s 'Comfortable' Penny Loafers Are Almost 50% Off, and Shoppers Say They’re 'Really Nice' for the Price first ...

but there’s one classic style that deserves a spot in every woman’s wardrobe: a pair of slim penny loafers.

Our top pick, the Allen Edmonds Randolph Penny Loafer, is a classic shoe that can be worn with both suits and jeans. If you want to go all in on comfort, we like Amberjack’s The Loafer ...

Best classic penny: G.H. Bass Whitney Weejuns - See at G.H. Bass A classic penny loafer will always be in style. G.H. Bass makes some of the highest quality leather loafers for women we've tested.

Most of our top picks are classic penny loafers, with accents ranging from lugged soles (thick rubber soles with deep indentations to provide solid footing) to metallic finishes. There’s even a ...

The Cary is another popular silhouette, which is The Row’s take on a classic penny loafer, with an unstructured upper and a throw-on quality, thanks to the supple leather and slip-on design.

Miu Miu’s penny loafers are some of the most-loved ... Sometimes, all you need is a classic brown suede loafer, and when you do, this pair from Rag & Bone should be at the top of your list.

Amazon Already affordable, these classic penny loafers are on sale for even less at Amazon’s Big Spring Sale. They look very similar to the pair Garner wore with her staple-filled early spring ...

In 2025, there are plenty to choose from whether it’s the patent black chunky sole shoe popularised by Prada in 2021 to penny loafers and the more “grandpa” style classic styles we’ve seen in recent ...