Chunky Loafers Can Be Hard to Style—These 8 Pieces Always Work With Them

Loafers, chunky ones in particular, have become a key staple in our shoe collections in recent years. It’s unsurprising, really, since they’re an easy, comfortable flat-shoe option that also makes anything you pair them with look polished. Whether you decide on the ubiquitous Prada ones or a more affordable alternative, it’s clear they make a smart investment—especially for the upcoming autumn and winter months. 


(Image credit: @threadsstyling)

The trouble is chunky loafers, with their masculine vibe and heavy appearance, can actually be quite hard to style. Jeans are one of our most-worn items and the obvious choice to wear with easy slip-on shoes, but even then you need to be careful with the shape and length of the denim. Your best bet, in a stylist’s opinion (that’s me), is to keep it classic. A tonal colour palette and pared-back basics will always look best. Think black jeans and camel coats. Worried about them feeling too clunky? Pair them with a mini or midi skirt for balance. Prefer to lean into the androgyny? Pair them with cargo pants for an extremely 2022 vibe. 

Keep scrolling, and you’ll find eight examples of easy outfits you can wear with your chunky loafers and the specific pieces we find always work with them. Most pieces you probably already own, but I’ve shopped out some options if you’re looking to fill any gaps in your wardrobe ahead of the new season

1. Miniskirts


(Image credit: @aniyahmorinia)

Loafers and miniskirts go together like bread and butter. The masculine shoe balances out a cutesy mini perfectly. Ankle socks optional. 

2. Leather Trousers


(Image credit: @eliinaolofsson)

As soon as the weather allows, we'll be whipping out our leather trousers again. And you can be certain we'll be wearing them with chunky loafers on repeat. 

3. Midi Skirts


(Image credit: @chainkyr/)

A controversial one, perhaps, but in a similar vein as with miniskirts, chunky loafers provide the perfect antidote to floaty midis, as proven here. Just add a knit for autumn and you're off. 

4. Camel Coats


(Image credit: @camillecharriere)

This might sound like a strange one, but from thorough research, it's clear that even if you wear the most "boring" outfit underneath, throwing on a camel coat with your chunky loafers immediately makes you look chic. 

5. Jumper Dresses


(Image credit: @hannahlewisstylist)

Dresses with loafers is a hard combo to pull off, but if you opt for jumper dresses or ribbed knitted styles, you can guarantee they will always work. 

6. Black Jeans


(Image credit: @juliesfi)

It may sound obvious, but if in doubt, a classic pair of black denim will save you any time you're having loafer-outfit struggles. 

7. Straight-Leg Blue Jeans


(Image credit: @lefevrediary)

Of course, the same applies to blue jeans. But straight-leg styles work best here, whether cropped or looser and full-length.

8. Cargo Trousers


(Image credit: @hannahlewisstylist)

Cargo trousers are about to be everywhere this autumn, which is good news for you and your chunky loafers since they partner perfectly for that slouchy, oversized look. If you're worried about everything looking too baggy and masculine, tuck in a tighter tank or roll-neck layer or wear them with a crop top to balance out the proportions. 

Up Next: 10 Major Shoe Trends That Will Be Everywhere This Autumn

Emily Dawes
Affiliate Editor

Emily Dawes is the very definition of a fashion multi hyphenate. An editor, stylist and writer with over eleven years’ worth of experience in the industry, Emily is known for her impeccable taste, elegant outfit choices and being able to spot the next big thing in fashion from a mile off. Our readers loyally trust her advice and shopping suggestions; so much so she began her own column documenting the most expensive-looking pieces on the high street, which has become a top-performing piece of content for the Who What Wear brand.

Emily has worked for Who What Wear UK since 2020 in a myriad as roles, spanning from contributing editor and branded content editor. Now, she holds the position of affiliate editor and is responsible for the brand’s overall affiliate strategy, ideation and content execution. Working closely with Who What Wear UK’s affiliate manager, Emily has been instrumental in securing and nourishing brand partnerships, surpassing her goals as standard. Leading the team in tentpole shopping moments including Black Friday and Peak Trading, with Emily’s guidance and leadership, team Who What Wear is in a stronger affiliate position than ever before.

Prior to joining the Who What Wear team, Emily served as YOU Magazine’s acting fashion editor where she managed the fashion team and oversaw all fashion content output for the fast-paced weekly title. Emily is a stylist in her own right, having worked with a slew of VIP clients including writer and television personality, Elizabeth Day, as well as styling and art directing several celebrity cover shoots for glossy print publication, Grazia. Her adept fashion knowledge means brands regularly sought out to work with her as a consultant: previously she has developed marketing and content plans for brands for Cocoon and Edge of Ember. Before entering the industry, Emily obtained a Bachelor of Arts in English and American Studies with International Study from Nottingham University. Fun fact: Emily spent a year studying in America which saw her join a sorority during her time there.

When she’s not working or tracking down the chicest, new-in items to share with our audience, you’ll find Emily bestowing her East London home with her stylish flair, reading everything from the classics to cowboy romance novels and escaping to the country with husband, baby boy and dog, Roo, whenever she can.

Emily is currently on maternity leave.