One of my most favorite shoes in my closet are my go-to Converse. I wear them ALL the time. I style them with my favorite jeans, shorts and yes, dresses. And I love pairing a dress with more casual shoes like a white Converse. It’s just so easy and effortless and makes every outfit feel a little more cool and casual. But that’s the thing, styling a dress with Converse doesn’t have to just be your casual dresses.
You can totally pair these with your slip dresses, a nicer silk dress you haven’t worn in ages because you aren’t getting dressed up as much, and of course, sundresses and t-shirt dresses. There are tons of ways to add this classic pair of shoes to the dresses you already have in your closet. I’d maybe just skip the formal dresses. There’s not much we can do in terms of dressing those down.
The best part of pairing your dresses with Converse? You can choose ANY style of Converse sneakers you like. From the classic Chuck, the Chuck 70 to even the platforms (my favorite) and high top Converse. Plus, so many fun colors and prints to choose from. Let’s get into it.
How To Style Dresses With Converse
Styling your favorite dresses with Converse is so easy. I promise! You can also mix up your Converse options. They don’t have to be a classic white Chuck Taylors. You can also try the platform Converse (my personal favorite) or even high-top Converse. And don’t just choose white, you can black Converse too. And you can even go bold and try fun colors. Whichever Chuck you choose, you can work them into any of these dress styles. I can guarantee you, the shoe is a classic and you’ll wear it for years too.
Silk Dresses With Converse
I love the juxtaposition of a silky pretty dress paired with a more cool and laid-back Converse. You can soften the blow by adding a layer that’s also casual to bring it all back together. This is truly how to make it feel much more intentional. Try a denim jacket or utility jacket to dress it down.
A mini silk slip dress with high top Converse and an oversized denim jacket is truly the perfect casual yet cool outfit. But to me, silky paired with cool edgy sneakers like a Converse, is the ideal way to combine these two. Below are my favorite silky dresses from slip dresses, minis, wrap dresses and more.
Maxi Dresses With Converse
Style a flowy floral maxi dress with your Converse for the ultimate spring combo. This is exactly how I’d style the two together. You can layer on a light jacket too here or a chunky cropped sweater for fall. Even a casual cotton tank maxi dress is great with a little Converse. It’s super casual and easy.
And lastly, a boho dress with puff sleeves or tiered ruffle layers is also great with a little white sneaker. Think anything Free People is perfect! When it comes to choosing a maxi dress for this combo, I would definitely lean into more casual dresses. You can get away with a mini silky dress, but something about a maxi just feels like you’re throwing on sneakers to leave an event in comfort.
T-Shirt Dresses With Converse
One of my go to looks is pairing a t-shirt dress or even a tank dress with Converse. It’s cool and casual and is great for spring summer and even fall. Yes you read that right! With the right jackets, you can wear this combination for many months out of the year.
For spring, add a lightweight denim jacket or utility jacket. You can skip the jacket for summer or try a white denim jacket if you need a light layer. And for fall, give me leather jackets! I especially love my platform Converse with this look too. And if you need a little something more interesting than just a t-shirt dress, there are plenty with cute ruching, knot details and so on to shop. Sharing all my favorites below.
Sundresses With Converse
A classic combination in my book. Summer calls for Converse and pairing them with your favorite sundresses is just smart fashion. They’re meant for one another. Like hamburgers and fries, ice cream and sprinkles. They’re just meant to be together!
I love a good white sneaker with a sundress and a Converse to me is the best choice over all my other white sneakers. No matter if the sundress is a mini, midi or maxi, it works! Add a straw bag and a denim jacket if you need it for the quintessential summer outfit.
Midi Dresses With Converse
Another combination I love is pairing my midi dresses with Converse. I personally prefer my platforms with a midi to add a little bit of height. A simple silky midi dress, or even a fitted cotton midi dress is the perfect piece to pair with your Converse for spring and summer. This also makes a really great travel outfit for exploring. It’s comfortable, you’re stylish, and it’s simple!
How To Wear Converse High Tops With Dresses
Now let’s chat high top Converse! These have quickly become my favorite Converse shoes to wear. I love them with my jeans and denim cut offs. But I especially love them with a mini dress for spring and summer.
I really like to pair my high top Converse (I love the platform lift ones the best) with mini dresses. Since a high top sneaker cuts off your leg a bit, it’s best to keep your dress on the mini side if you can. If you did a midi dress, the proportions may feel a bit off. This is really just a preference and if you have long legs, I feel like you can totally rock this combo.
You can also pair your high top Converse with a maxi dress if you like. I think these are just as versatile as the classics but have a bit of a cooler edge to them.
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