The Best Sneakers To Wear With Long Dresses

Last Updated on February 18, 2026 by Martina McKeough

When spring and summer come round it’s time to shed the jeans and jumpers and get out some of the other clothes that have been lying dormant for months. The warmer seasons are the perfect time to start wearing dresses again and in particular longer maxi styles. I’m not going to talk about dressing them up but I would like to discuss the best sneakers to wear with long dresses for a relaxed casual vibe.

Sneakers are one of the most versatile styles of footwear you can have in your wardrobe and having the right styles means they become an absolute closet essential. Here are some of my favorite types of sneakers that work well with long dresses as well as plenty of other outfits in your wardrobe.

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White Sneakers

If you are going to only buy one type of sneaker for the hotter months it has to be a pair of white sneakers. Crisp white sneakers have a great feminine edge but are also incredibly comfortable and practical.

White sneakers are perfect for daytime outings, city walks or for travel and they go with absolutely everything.

I like chunkier cushioned styles for when I’m doing plenty of walking and revert to minimalist neater styles when the occasion is a little more formal.

If you can buy ones that are made from leather or are breathable so your feet don’t sweat in them in the heat. Plus this type of style will be easier to keep clean. A magic eraser is my top tip to use if you want to get off any scuffs or marks.

My current favorites are:

Veja Campo Sneakers

Cole Haan Crosscourt Joy Sneaker

Retro Sneaker Styles

In the past couple of years retro sneaker styles have been back with a vengeance with brands such as Adidas and Puma trawling their archives to make old style trainers relevant again. This trend has taken off in a big way and shows not sign of stopping just yet.

This look has branched out from the cool kids and into the mainstream and just about every footwear brand has now created a version of this look to sell.

You can stick with the simple black and white or black and blue styles or mix it up and buy one of the more colorful designs. I’ve noticed that pinks and greens in particular have been hugely popular making this look both feminine and vintage at the same time.

Again this look is perfect for casual weekends, bruch and errands.

Adidas VL Court Sneaker

Keds Rena Sneakers

Canvas Sneakers

The next ever popular style are Canvas Sneakers. Whilst tennis shoes could be considered part of this trend sneakers like Converse or Vans are timeless and match almost every pattern.

This style of footwear has a relaxed, casual but on trend feel and the style tends to pair well with floral or long maxi dresses.

I know that this style is usually associated with a youth trend but done right this can work for any age. Just make sure that you add extra cushioning by using insoles if you need more support as this style of sneakers isn’t always so forgiving on your feet especially as you get older.

Converse All Star Madison Sneakers

Chunky Sneakers

Chunky sneakers work surprisingly well with long dresses because they create balance. A maxi or midi dress often has movement, softness and flow, so adding a substantial shoe grounds the outfit and stops it from feeling overly delicate or dressed up.

The thicker sole also gives you a little extra height, which helps prevent longer hemlines from dragging and keeps proportions flattering. Instead of competing with the dress, chunky sneakers create contrast and that contrast is what makes the outfit look styled rather than accidental.

Their popularity really took off in the mid-2010s when fashion houses like Balenciaga introduced exaggerated “dad” sneakers such as the Triple S. What started as a bold runway statement quickly filtered into street style, with influencers pairing oversized trainers with floaty dresses, tailoring and feminine silhouettes. That high-fashion endorsement shifted chunky sneakers from purely practical footwear into a trend-driven wardrobe staple.

Today, chunky sneakers feel modern rather than clunky. They add edge to floral maxis, give slip dresses a street-style twist and make long knit dresses feel effortless. If you want comfort without sacrificing style, they’re one of the easiest ways to make a long dress look current and fashion-forward.

Steve Madden Possession Sneaker

Sneakerinas or Ballet Sneakers

This next style of sneaker is one of my current favorites at the moment and it is the sneakerina trend that has really come into its own over the last couple of years.

I love ballet flats and wear them everywhere so it makes sense that sneaker designers started to incorporate a similar look into their designs. What I love about this look is that they are more wearable because of their comfort in casual settings.

The interesting thing about this style of sneaker is that there are so many different types of design to choose from. I’m currently in love with my Puma Speedcats in black satin. They are slip on with elasticated fronts and are some of the most comfortable shoes I have ever worn.

Alternatively you can go for the mary-jane styles in either a minimalist look or alternative in a chunky design. Just pick a color and style and wear then with a long boho or floral dress and you can’t go wrong.

Puma Speedcat Ballet Sneakers

Adidas Barreda Mary Jane

Sporty Sneakers

The best sneakers to wear with long dresses

If you are a fan of the sporty look then my next type of sneakers is for you. I’m not talking about sporty in the traditional sense of wearing something to play sports in. Instead I’m thinking of minimalist style dresses that work well with the type of sneakers you would wear to the gym.

Think jersey long dresses with slits in the side and that look that makes you seem as if you have been lounging at your country club during the day.

This look works best when you keep accessories to the minimum and the dress simple. Neutral colors like white, black or taupe work particularly well and keep the outfit looking classy.

New Balance 574 Core Sneaker

Platform Sneakers

The Best Sneakers To Wear With Long Dresses

Finally last but not least I have to mention platform sneakers because they give you extra height which is useful for longer hemlines.

This look can be harder to pull off as you can look like a Spice Girl in the 90’s if you get it wrong. It is also a look that often looks better if you are younger.

However I’m a great believer in giving everything a try as with the right outfit, sneakers and attitude anyone can pull a look off.

Dr Scholl’s Time Off Sneakers

Styling Tips For Dresses and Sneakers

As ever there are tips that can make things easier for you. Here are just a few that can help you make sneakers and dresses work.

Balance Proportions – Bulkier sneakers work well with flowy dresses and help keep your outfit grounded.

Choose Sneakers That Go With Everything – If you don’t have a massive budget for different types of footweard stick with neutral colors that go with everything.

Show Some Ankle – If your dress has a slit or a tier it can really help visually tie your sneakers into the look.

As you can see the best sneakers to wear with long dresses don’t have to be identical. There are so many options and styles out there that you can play around with that can help create an amazing look for the warmer months.

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