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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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 – buy now
Samba OG Trainers, £89.99, adidas – buy now
Chuck 70 Vintage Canvas, £85, Converse – buy now
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, £49.99, Office – buy now
Block Heel Leather Pumps, £179, Arket – buy now
Chunky Block Heel Sandals, now £53, Charles & Keith – buy now
Rhinestone block-heeled shoe, £79.99, Mango – buy now
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 – buy now
Chunky loafers, £37.99, H&M – buy now
Leather penny loafers, £89.99, Mango – buy now
Contrast Loafers, £35.99, Zara – buy now
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.
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, £349, AllSaints – buy now
Heeled ankle boots
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 – buy now
Romeo suede platform boots in pink, £70, ASOS DESIGN – buy now
Track Sole Ankle Boots, £45.99, Zara – buy now
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 – buy now
Contrast panel western boot in black, £59.99, Pull&Bear – buy now
Western Cowboy Boots, £225, & Other Stories – buy now
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
Luke – Black Patent Leather Ballet Flats, now £151, Alohas – buy now
Red Wide Welt Buckle Ballerinas, £295, Ganni – buy now