Chunky Loafers Are Back In For Fall, And We Love These 8 Pairs

Every autumn, as the weather turns chilly and Starbucks starts vending pumpkin spice lattes, I swap my summer sandals for a perfectly broken-in pair of brown leather loafers — and inevitably catch some good-natured digs about my “grandpa shoes.”

Even I have to admit my trusty flats are a little bit librarian chic. But back in the 1990s, when Steve Madden shoes topped every cool teen’s holiday wishlist, chunky loafers were anything but staid. With their square toes and sturdy heels, the leather stompers lent even school uniforms a punk-rock lilt. 

View this post on Instagram

A post shared by Russell & Bromley (@russellandbromley)

And now thick-soled loafers are making a comeback. Joining other ’90s trends in the 21st century, the shoes are all over Instagram feeds and street style shots. Influencers and celebs like Selena Gomez wear them with denim (try kick flares or mom jeans) or a skirt and ankle socks.

If you want to kick off fall in this nostalgic style, read on — we scoured the Internet for the best chunky loafers.


Hefty loafers, meet high fashion. I love the scalloped edge on the sole of these Prada shoes.

chunky loafers

SHOP – $975

Want to try the trend without handing over too much cheddar? Nab these chunky, already-affordable loafers while they’re on sale.

chunky loafers

SHOP – $53.98

The Steve Madden originals — with a candy-colored twist. I’d pair these alongside a white smock dress and let the baby pink leather steal the show.

pink leather loafers

SHOP – $99.95

Ch-ch-ch-chainlinks. The silver metal adornments freshen up these loafers’ super ’90s stitching.

chainlink loafers

SHOP – $160

Who said heavy duty loafers can’t be ladylike? Designed with a slingback and embellished with little crystal flowers, these chunky loafers beg to be worn with cigarette pants and a puff-sleeved blouse.


SHOP – $375

I’m delighted by the way these transform traditionally buttoned-up trends (penny loafers and pearls) into something so rock and roll.

chunk loafers

SHOP – $495

I love these loafers as a perfect middle ground between the chunky trend and my usual preppier flats: the horsebit detail keeps it classic, while the lug sole adds an edge.

laurs platform loafers

SHOP – $150

Height seekers, these chunky loafers are for you. The best thing about those big platform soles? Even four inch heels stay pretty darn comfy.

platform loafers

SHOP – $59


How do you plan on styling your chunky loafers? What footwear trend should we cover next? Share with us in the comments!

For More Shoe Trends, Read These Articles:

Dad Style Is In And We’re Loving These Dad Sandals Right Now!

Need A Transitional Piece? Try These Ankle Boots You’ll Want To Wear All Autumn Long

Join the Conversation