Shoes to wear with dresses: a guide
Reading time: 3 minutes | Last updated: June 11, 2025
Let’s be honest – finding the perfect pair of shoes to match a dress can be tricky. They’ve got to look great, feel even better, and carry you confidently from brunch to bedtime. Lucky for you, at Wolky, we’ve got just the thing.
We’ve been designing comfort shoes for over 40 years – each pair handcrafted in Europe using only top-tier materials. So if you’re on the hunt for shoes that work with dresses and work for your feet, read on!
Let's find the best shoes to wear with dresses
Here’s your go-to guide to the best types of shoes to wear with dresses. Bonus: we’ve included our top Wolky picks for each one!
Sandals
Why they work: Sandals bring a relaxed, breezy vibe to any outfit – perfect for sundresses, maxi dresses, and warm-weather getaways. Look for cushioned footbeds and adjustable straps for all-day comfort.
💙 Wolky’s pick: Jewel – A customer favorite, thanks to its ultra-supportive footbed and adjustable fit.
Breezy sandals
Loafers
Why they work: Loafers offer clean lines and a chic, structured finish. They’re ideal for shirt dresses, midi styles, and dressed-up casual looks.
💙 Wolky’s pick: Alabama F2F – A comfortable loafer that delivers on comfort and style.
Sandals with heels
Why they work: A low to mid heel adds polish without sacrificing comfort. At Wolky, we’ve made sure the heels don’t compromise walkability. Perfect for date nights, summer weddings, or dressy daytime events.
💙 Wolky’s pick: La Jolla – All the style of a heel, with the support your feet deserve.
Cute sandals with heels
Mary Jane shoes
Why they work: The iconic strap gives you security (no slipping heels!) and a little retro flair. They look especially cute with A-line and swing dresses.
💙 Wolky’s pick: Passion – Retro charm meets all-day comfort in this stylish Mary Jane.
Retro Mary Janes
Boots
Why they work: Ankle boots add structure and contrast to softer dresses. If you’re looking for a cool look, go for a pair of boots. They’re perfect for transitional weather and give your outfit a little edge. In short, perfect shoes to wear with dresses!
💙 Wolky’s pick: Red Deer WR – A rugged-yet-chic boot that pairs perfectly with layered looks.
Flip flops
Why they work: Great for beachy looks and laid-back summer styles. But beware – choose flip flops that support your feet. Maybe a pair of Wolky’s?
💙 Wolky’s pick: Tahiti – A stylish flip flop that cushions and supports with every step.
Supportive flip flops
Long boots
Why they work: Tall boots bring extra style to your dress game. Ideal for cold winter days, when you want your calves to be protected from the cold. Wear them over tights or with over-the-knee styles for a wow factor.
💙 Wolky’s pick: Hayden – Sleek leather, a perfect fit, and serious winter vibes.
Long boots
So, what shoes with dresses will you wear?
Dresses and shoes are a timeless duo that can be tricky to pair just right. Luckily, we know all about it. Whether you’re into breezy sundresses or sleek knit midis, there’s a Wolky shoe that’s made to match – designed for walking, built for comfort, and totally dress-worthy. Whatever your style, there’s a Wolky that suits your wants and needs.
Do you need online advice about shoe choice?
Contact us through the options below, and we’ll be happy to assist you.
Commenting on this blog?
Relevant blogs
Good choice!
These shoes are of excellent quality. With proper care, they'll stay beautiful for a long time – sustainable for the planet and smart for your wallet. Our maintenance tips: