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Which Shoes Should You Wear With Dresses? 7 Styles That Work Every Time

Don't be confused this time.

Last Updated on September 26, 2023

Wondering what shoes to wear with dresses? Here, I’m sharing 7 footwear styles that work every single time to take the stress out of getting dressed, whether you’re heading to the shops or to a black tie event.

Knowing what to shoes to wear with dresses can be tricky. When I was growing up, I used to think that dresses must be worn with heels, while sneakers were best paired with trousers or jeans. As we know now, sneakers go with pretty much anything and everything.

Rules are meant to be broken anyway, especially in fashion. Where’s the fun in following what everyone else is doing? Don’t be afraid to try out new things and experiment with your own personal style. But there are certainly times when you feel more inspired than others, or when styling leaves us feeling overwhelmed.

So if you’re struggling to work out what shoes go with dresses, I’m here to help. Keep scrolling for 7 styles that work with any dresses. Next, shop some great shoes from our Amazon edit or check out the best new shoes for autumn winter 2023. We’re also laying out the biggest shoes and boots trends for 2023.

Now, let’s go back to chic ways to style dresses and shoes.

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woman wears skirt and adidas sneakers at fashion wee

When you’re planning to be on your feet all day, choose comfort by teaming your dresses with sneakers. This styling combination is like peanut butter and jelly; it’s not just timeless, but it always looks cool. Classic sneakers such as Converse and adidas Sambas work with most dresses, including flowy maxis, minis and shirt dresses.

530 Sneakers, £110, New Balance at & Other Stories

530 Sneakers, £110, New Balance at & Other Stories – buy now

Samba OG Trainers adidas

Samba OG Trainers, £89.99, adidas – buy now

Chuck 70 Vintage Canvas Converse

Chuck 70 Vintage Canvas, £85, Converse – buy now

Block heels

woman wears prada bag and shoes at fashion week

Channel your inner French girl with classic block-heeled shoes. These are great because unlike stilettos, they’re easy to walk in and super comfy to wear – promise! Wear yours with midi or mini dresses as they elongate your legs.

Marvel Triple Strap Mary Jane Block Heels Office

Marvel Triple Strap Mary Jane Block Heels, £49.99, Office – buy now

Block Heel Leather Pumps Arket

Block Heel Leather Pumps, £179, Arket – buy now

Chunky Block Heel Sandals

Chunky Block Heel Sandals, now £53, Charles & Keith – buy now

Rhinestone block-heeled shoe Mango

Rhinestone block-heeled shoe, £79.99, Mango – buy now


Woman wears loafers shoes at copenhagen fashion week
Noor-u-nisa Khan

Loafers are another foolproof option, whether you’re wearing a feminine dress with ruffles and lace or a knitted maxi dress. Add a pair of white or black socks to give it a preppy look.

For inspo, check out the best Prada loafers dupes next.

Memoir smart loafer in black, £28, ASOS DESIGN

Memoir smart loafer in black, £28, ASOS DESIGN – buy now

Chunky loafers H&M

Chunky loafers, £37.99, H&M – buy now

Leather penny loafers Mango

Leather penny loafers, £89.99, Mango – buy now


Contrast Loafers, £35.99, Zara – buy now

Over-the-knee boots

woman wears bottega veneta bag, blazer dress and boots

I love mini dresses as much as the next person, but when it’s cold outside, they take a backseat in my wardrobe. Not anymore! I’m wearing mine with over-the-knee boots, which keep my legs toasty and look stylish too. These boots work with any length of dress of course, but mini dresses give them the attention they deserve.

TOPSHOP LIMITED EDITION Freya premium leather thigh high square toe boot in silver

Freya premium leather thigh high square toe boot in silver, now £150, Topshop – buy now


Flat Track Sole XL Boots, £59.99, Stradivarius – buy now

Reina Knee High Leather Boots AllSaints

Reina Knee High Leather Boots, £349, AllSaints – buy now

Heeled ankle boots

Woman wears dress and boots at london fashion week

Heeled ankle boots are a no brainer. These give a little bit of height and elongate the legs, all while making your outfit that little bit smarter.

Leather Ankle Boots, £199, Arket

Leather Ankle Boots, £199, Arket – buy now

Romeo suede platform boots in pink ASOS DESIGN

Romeo suede platform boots in pink, £70, ASOS DESIGN – buy now


Track Sole Ankle Boots, £45.99, Zara – buy now

Cowboy boots

woman wears cowboy boots and dress to copenhagen fashion week
Noor-u-nisa Khan

The cowboy boots trend is going no where. If you’re wondering how to wear them, they work with pretty much any dress, from boho-style maxi dresses to sequin minis, as spotted above at Copenhagen Fashion Week.

Embroidered Leather Cowboy Boots, £290, COS

Embroidered Leather Cowboy Boots, £290, COS – buy now

Pull&Bear contrast panel western boot in black

Contrast panel western boot in black, £59.99, Pull&Bear – buy now

Western Cowboy Boots & Other Stories

Western Cowboy Boots, £225, & Other Stories – buy now

Ballet flats

Woman wears dress and ballet flats at fashion week

Ballet flats are another of AW23’s biggest trends, and what better way to style them than with a dress? For a daytime look, wear yours with a maxi linen dress or wear them with a slip dress in the evening.

Los Angeles ruched ballet with elastic strap in rose, £18, ASOS DESIGN – buy now

Los Angeles ruched ballet with elastic strap in rose, £18, ASOS DESIGN – buy now

Luke – Black Patent Leather Ballet Flats, now £151, Alohas

Luke – Black Patent Leather Ballet Flats, now £151, Alohas – buy now


Red Wide Welt Buckle Ballerinas, £295, Ganni – buy now

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