My journey to accepting the notion that sneakers had officially become a fashionable footwear staple was, admittedly, a long one. However, a couple of years ago, I finally began to start experimenting with the fashion-girl-approved trend, and quickly learned that it was going to be pretty hard to ever go back to wearing my previously beloved ballet flats. I love a sartorial juxtaposition, and any look that’s styled with something unexpected, which is why I’m always scouring Instagram and street style blogs to discover new sneaker and dress outfit ideas to copy. Hey, I have no shame in “borrowing” styling tricks from others to test drive myself. Aside from the given that sneakers tend to be pretty damn comfortable and city-girl-friendly, they also just so happen to make any lewk just a little bit cooler.
While I personally love an unapologetically feminine look, complete with a bubblegum pink ruffled maxi dress and strappy heels (my go-to), when I see influencers and street style stars pairing their cocktail-worthy frocks with beat-up sneakers or finishing off a fitted mini dress and jean jacket get-up with chunky dad sneakers, I can’t help but swoon. In fact, this ridiculously easy and infinitely versatile outfit formula has really become an integral part of my wardrobe lineup. I work in a fairly casual office dress code wise, and while I always tend to err on the side of caution when it comes to wearing what I deem appropriate versus inappropriate for office attire (I still take an old fashioned stance on hats), I’ve even gotten away with sporting a midi dress and my favorite Reeboks in workplace. Of course, plenty of fashion editors and bloggers rock this look at fashion week to shows and upscale after-parties without looking too daytime, too. Seriously, the sneaker-dress template is a lot easier to pull off than you think. If you need a bit of inspo to get you on board with it, I’ve rounded up some examples c/o some of Instagram’s most stylish accounts to help you nail the look.
1. Breezy White Midi + Leather Moto Jacket + Black Sneakers
A flattering LBD that you’ll definitely wear on repeat.
Everyone should own a vegan leather moto jacket.
The pair of sneakers I’ve been coveting for over a decade *swoon*.
2. Cocktail Dress + Stan Smith’s
Pink, polka dots, and ruffles. My three favorite things in one adorable frock.
You can’t go wrong with these O.G. sneakers. They literally go with just about anything.
3. Pink Jacket + Polka Dot Slip Dress + Reeboks
This adorable midi is also marked down from $148 at the moment.
Denim jackets are 100% a staple outerwear piece, and this one gets bonus points for its baby pink hue.
A vintage hero with a contemporary twist.
4. Slinky Satin Mini + Chunky Black Hi-Tops
That one Instagram-famous dress that I am *also* obsessed with.
The unlikely sneaker choice that magically makes any look a tad cooler.
5. Floral Midi Dress + Chunky Dad Sneakers
Curve-hugging midi dresses are proving to be the most complimentary accessory for pairing with sneakers.
I have mixed feeling about the whole dad sneaker trend, but these I can get on board with.
6. Slip Dress + Tee + Converse All Star’s
Tie-dye has shaped up to be one of the summer’s biggest retro-revival trends, and it shows no signs of slowing down come fall.
The basic white crew neck tee is such an underrated closet staple that deserves a bit of attention.
The pair of sneakers in your closet that will look just as cool brand new as they will after a decade of wear and tear.
7. Ladylike Dress + Luxe White Sneakers
The perfect lady-like dress to toughen up with some sneakers.
The luxe answer to classic the classic Stan Smith style.
8. Satin Slip Dress + Cardigan + Vans Old Skool Sneakers
An unexpected color choice that gives a fresh take on the silky slip dress craze.
Texture can make or break a look.
The chicest skater shoe we ever did see.
9. Mini Dress + Boyfriend Blazer + Chunky Sneakers + Baseball Cap
The sweetest mini slip I’ve ever laid my eyes on.
You will wear this blazer on repeat this fall. Trust me.
Fila is officially back in action, guys.
The cap you didn’t know was missing from your current lineup.
10. Floral Maxi + Denim Jacket +Chuck Taylor Hi-Tops
The perfect floral maxi that will work for just about any occasion and any season.
The perfect oversized (but not too baggy) jean jacket.
A timeless sneaker staple.
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