It’s safe to say that sneakers have had an interesting year. Ugly sneakers have become somewhat of a cultural phenomenon with major designers like Balenciaga and Calvin Klein starting the trend before it trickled down into mainstream stores like Adidas, FILA, and even Skechers.
You’ve probably already seen the chunky-soled, Seinfeld-like sneaker on plenty of celebrities and fashion bloggers. While I’m totally on board with comfier footwear, I can’t help but scratch my head and say, “There’s gotta be a better way to do this.”
Perhaps one of the most interesting aspects of this ugly shoe trend is that most women are wearing these clunkers with skirts and dresses. The combination is typically worn by fashion’s elite in an ironic manner, and the extreme juxtaposition is a fashion statement, rather than an attempt to create a beautiful outfit.
The thing is, there is a way to wear sneakers with skirts and dresses that is equally fashion-forward and lovely. Most women would agree that sneakers are much more comfortable than high heels or even ballet flats, but the problem is they don’t know which sneaker styles would go with a dress or skirt.
The thing is, there is a way to wear sneakers with skirts and dresses that is equally fashion-forward and lovely.
To help you learn how to wear sneakers with the more girly items in your closet, I have a few tips on which shoes to choose and how to style them.
Little White Sneakers
You can’t go wrong with a little white sneaker. Perhaps the most versatile shoe you could own, a white or cream sneaker can be worn with any other color in your wardrobe and with plenty of skirts and dresses. Because the body of the shoe isn’t bulky and the sole is flat, this nondescript shoe style is more like a super casual flat than an actual sneaker. Converse, Superga, Adidas, Feiyue, and Vans all carry classic white sneakers.
The little white sneaker is best for warm weather months, and it pairs well with light-weight dresses and skirts.
The little white sneaker is best for warm weather months, and since it already has a summertime vibe, it pairs well with light-weight dresses and skirts. If you’re a little nervous about this unconventional combo, begin by wearing dresses or skirts that also have white in them to match the shoes. The matching whites will create cohesion in the look overall so you won’t feel like they’re too contrary.
Sleek Running Shoes
This is the trickiest sneaker and dress combo to pull off since running shoes are typically associated with working out. But fear not, there is a way to make it work. The key to wearing running shoes with a dress or skirt is to keep this term in mind: sports luxe. The sports luxe trend is all about streamlining workout wear, minimizing bulk for a minimalist appeal. The end result is an ensemble that is polished and futuristic. So when choosing a running sneaker that you can wear with dresses or skirt, opt for sleek silhouettes. This means aerodynamic styles with minimal bulk. You also want to make sure the sole isn’t chunky, but smooth like the body of the shoe. Nike Flex is a great option, as well as Adidas’ Edge Luxe 3.
Choose a dress or skirt that is sleek like the shoe.
When styling an outfit to go with your sleek running shoes, take inspiration from the shoe itself - sporty yet sophisticated. Instead of wearing super feminine dresses with frills, ruffles, and the like, choose a dress or skirt that is sleek like the shoe. Think loose, silky sheath dress or a stretchy black pencil skirt worn with a casual t-shirt.
Ankle Hugging High Tops
Similar to the little white sneaker, canvas high tops work great with dresses and skirts. The deconstructed body of a high top allows you to tie it close to your ankle, following the natural line of your foot more seamlessly than a bulky Nike high top would. Because the silhouette of the shoe is more formed to your foot and ankle, it looks less gym ready and more street style ready. Plus, the canvas high top is also more reminiscent of a boot because of it’s tall laces, and as we already know, boots look great with skirts and dresses.
Because the silhouette of the shoe is more formed to your foot and ankle, it looks less gym ready and more street style ready.
In fact, shoes like Converse high tops look especially cool with skirts and dresses. The best outfits are the ones where there is both contrast and complementarity between differing items. This creates balance. In the instance of dresses and sneakers, there is a balance between femininity and masculinity. The more masculine shoe anchors the rest of the outfit and toughens it up a bit for an effortlessly cool street style look.
Another key component is that canvas high tops have been around for decades and have a vintage appeal to them. When wearing high tops with more vintage inspired dresses or skirts, you create a look that is overall more classic which creates an overall cohesion in the ensemble. As already mentioned, Converse has the classic high top we all know and love, but PF Flyers and Po Zu also carry the iconic style.
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