7 Comfortable Fall Shoe Trends to Carry You Through the Season

Penny Loafers

The penny loafer is a huge fall footwear trend, and it just so happens to be extremely wearable. “The penny loafer is a true classic making a comeback. With their sleek, timeless. The preppy and collegiate aesthetic is still going strong and celebrities like Hailey Bieber and Kendall Jenner have been seen incorporating them into their everyday looks,” says Cynthia Kennedy, a personal fashion stylist in San Diego. “They’re the kind of shoe that instantly makes jeans or trousers look more polished without sacrificing comfort.” 

Derby Flats

With their flat sole, soft construction, and lace up detailing, derby flats are the ultimate comfy fall footwear trend you’ll be seeing a ton of this season. “Michael Rider, creative director of Celine, brought these shoes into the limelight for his spring 2026 show, and they are already being spotted on It-girls around the world,” says Janette Ewen, designer and creative director at Parker Barrow Design. 

She says to layer ankle socks or a thin, ribbed wool sock under your derbies. You can pair this footwear with casual styles or with more buttoned-up daytime work attire.

Jeweled Flats

Love the idea of a heel-free life but need a bit more spice? Bejeweled flats are for you. “These are a ballet-style flat with Mary Jane influence, and jeweled for an elevated feel,” explains fashion expert Dawn Del Russo. “Starlets like Dua Lipa have been seen wearing these styles, which gives it a boost of interest. Plus, women are looking for comfort, but not a frumpy shoe.” Style them with a shorter length skirt and blazer for a sophisticated, playful look or try an all black pants and top look. 

Earth-Toned Sneakers

Sneakers remain a go-to shoe trend that won’t be going anywhere, but this fall it’s all about simple, luxe neutrals. “Shades like beige, brown, or off-whites in leather or suede are clean, versatile, minimal, and rich-looking,” Kennedy tells us. “These sneakers give that ‘quiet luxury’ vibe while still offering the street style that celebs like Selena Gomez and Gigi Hadid can’t get enough of.” 

Try dressing them up with a slip dress and blazer, or you can keep it more casual with jeans, ball cap, and a trench. Neutrals literally go with everything, so you’ll want to wear them Sunday through Monday.

Boat Shoes

Boat shoes are a casual, moccasin-like shoe made with a non-slip rubber sole and laces around the shoe with grommets. Right now, they’re especially trending in brown tones. “This is a timeless, comfortable shoe with a preppy style. We’ve seen it on the Miu Miu runways and it’s also a classic from the ‘90s,” Del Russo tells us. “The cool girls are pairing them with oversized baggy denim. I would also suggest styling with an off white pair of denim cashmere sweater, and a matching trench.” 

Flat Riding Boots

Drop the heel and pop on a pair of flat riding boots. This trend nods to the Western aesthetic dominating right now, as well as the “frontier” boho look. 

“Classic flat knee-high riding boots are sleek, timeless, chic, and way more comfortable and practical than heeled boots,” Kennedy says. “Designers like Hermès and Tory Burch brought back the classic silhouette, and it fits right in with the polished-but-comfy mood of this fall.” Tuck in leggings or skinny jeans, or wear them with a midi skirt and a simple sweater. 

Shearling Lined Clogs

Who knew there’d be a day when clogs came back, but that day has come and these kicks are surprisingly comfy. Add a soft cushy layer of shearling and you’ll be living in them all season. 

“They feel like comfy slippers, but with enough style to wear out,” Kennedy says. “They also have a Scandi-chic look, which pairs great with the whole ‘comfort is the new luxury’ movement. Influencers and fashion girls are already pairing them with chunky socks for that cozy-but-intentional look.”