As someone who is only five feet, I figured out how to style chunky loafers from a young age. I’m always on the hunt for chunky shoes with a platform to give me a little boost, and a pair of slip-on loafers is one of my favorites.
And though they’re often associated with fall fashion and academic-inspired ensembles when school is back in session, they actually work year round. The versatile shoe offers a lot of range, pairing just as easily with a pair of wide-leg jeans as it does with a shorter dress or skirt. It fits in with your casual outfits as much as it does with your more office-appropriate ones.
From penny loafers and tassel loafers to leather and suede variations, there are so many different iterations of the tried-and-true shoe that can fit seamlessly into your closet, no matter your personal style. Ahead, get all the fashion inspo you need for how to style chunky loafers. These six outfit ideas and style tips will inspire you to try them out for yourself.
Classic + Preppy
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For a timeless chunky loafers outfit, go for a tweed minidress and a long coat. Compared to shoes with a narrower silhouette, these lug sole loafers amp up the volume for a more updated take on the classic shoe style. Round out the outfit with some gold jewelry and a black leather purse with gold-tone hardware to match. In the winter, simply add a pair of sheer tights layered under the socks for extra warmth.
Dream Pairs Loafer
Caslon Tweed Sleeveless Shift Dress
X-Cheng Fleece-Lined Tights
Jenny Bird Lennon Hoop Earrings
Streamlined Set
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If you’re still testing the waters of how to style chunky loafers, you can never go wrong with a matching set. The burgundy leather hue of the jacket and midiskirt above plays particularly well with black leather loafers, but go with whatever color combination works best with your personal style. For cooler weather, opt for a turtleneck instead of a T-shirt; you can always layer a light cardigan under the jacket for extra warmth too.
Coach Jocelyn Loafers
Treasure & Bond Pleated Satin Midi-Skirt
Rails Dria Faux-Leather Jacket
Mango Satin Blouse with Draped Neck
Edgy Chic
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A moto jacket is actually one of my favorite things to wear with a pair of loafers. Despite the shoes’ preppy origins, they have a remarkable flexibility and pair just as easily with polished and put-together aesthetics as they do with more edgy, streetwear-inspired outfits. Throw on a simple silk or satin midi with your loafers and finish off the look with a pair of sleek sunglasses.
Kate Spade New York Blake Platform Loafer Flat
Sam Edelman Lambskin Moto Jacket
Btfbm Long Satin Skirt
Sojos Cateye Sunglasses
Cozy Neutrals
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Dress up your leather loafers with a cozy zip-up jacket, a miniskirt, and tights for an easy outfit you can throw on for brunch. With some bright white socks, the chunky sole loafers are sure to stand out. Stick with a grayscale palette or one of earthy browns and cream for a subdued, old-money feel.
Zara Lug Sole Loafers
Alo Accolade Hoodie
Madewell Alonzo Coat
Pandora Organically Shaped Stacking Rings
Color-Coordinated
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This look is a master class in color-coordination from head to toe, tying together pops of blue, tan, and black across garments that each have a very different vibe to form one cohesive ensemble. If you’re looking to re-create the outfit for yourself, wear loafers with pieces that all share a common color story.
Sam Edelman Leah Platform Loafers
Cider Striped Knit Polo Top
Iswee Genuine Leather Shoulder Bag
J.Crew Patch-Pocket Mini Skirt in Corduroy
Polished + Professional
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A pair of chunky loafers and some wide-leg pants (or straight-leg jeans, if you’re not a fan of slacks) are a match made in heaven. The thickness of the loafer provides a platform for the fabric of the pants to drape perfectly around the ankle. Throw on a blazer or a short trench coat on top for a look that’s relaxed and business casual. And because the rest of the outfit is so simple, there’s room to play with a personality purse.

