As someone with both sensitive feet and a love of beautiful high heels, choosing shoes is not easy. My job makes it extra difficult, since I don’t always know how long I’ll be standing, how far I’ll be walking, or what kind of terrain I may have to traverse on any given day. Even sensible heels with Nike Air technology are uncomfortable when you’re running on cobblestones, and ballet flats aren’t very delightful when they’re soaking wet and covered with mud.

In the 90s, I generally just threw on a pair of Converse or Birkenstocks with just about anything and that was that. In college and for a few years after, it was mainly flip flops or those frat boy gray New Balances, though I also sported some flourescent pink Roos on more than one occasion.

In recent years, I’ve tried to keep my sneaker-wearing to errands, walking to the Metro and trips to Disneyland. But I have to admit I was stoked when I saw that sneakers are totally in this year. Now there’s no reason to keep my affinity for trainers a secret, even though I can’t wear them to work (most of the time).

Still, I know some of you may not be used to rocking sporty shoes outside of the gym at all, let alone with skirts and dresses. That’s why I’m here to help!

Freshman
    

The easiest and most obvious way to wear sneakers — just about any sneakers — is with a casual outfit like jeans and a sweater or T-shirt. You can keep it simple, or dress the whole thing up by choosing extra fun sneakers and adding a statement necklace or chandelier earrings. And, of course, this works with black jeans, white jeans, colored jeans or plain old blue jeans.

JV
Dressier pants, skirts and dresses are a little bit trickier, but if you choose the right sneakers, you’re golden.

Classic low-top sneakers — think Keds, Supergas, Vans and Converse — tend to be the most versatile, pairing well with skirts, dresses, printed pants, shorts and just about anything else. Try one of these combinations on for size:

Details:  Forever 21 cropped top, F21 skirt, red Supergas, Gap striped dress, Gap jean jacket, Anchor-print Keds, H&M top, Zara neoprene skirt, Converse, Zara T-shirt, Zara print pants, galaxy Vans

Varsity
More athletic-looking sneakers tend to offer more support, and come in a wide range of fun colors and prints. They don’t work with quite as many types of outfits, but they can still be worn more often than you think.

Typically, fitted or shift dresses and skirts work better with this style of shoes than full skirts or fit-and-flare dresses. As far as print and overall style, I tend to like tomboy-style dresses for an overall athletic look, or something floral or girly to contrast with the sportiness of the shoes. The key is to make sure the colors of the outfit and the colors of the shoes work together — whether that means they match, contrast or just clash in the perfect way:

Details, Row 1: Zara dress, Target necklace, Zara blouse, Gap pants, New Balance sneakers
Row 2: Gap shirt, Gap skirt, H&M sweatshirt dress, BaubleBar bracelet, The People’s Movement sneakers
Row 3: Target floral dress, Target moto jacket, Zara dress, BaubleBar ear cuffs, Forever 21 sneakers
Row 4: Zara blouse, Gap linen pants, Francesca’s dress, Francesca’s necklace, Nike sneakers

More tips for wearing trainers

Sock it to me: Regardless of what type of sneakers you wear, I’d avoid a thick rubber sole, and ditch the white athletic-style socks, unless you’re going for the 80s Working Girl look. If you have to wear socks, some kind of low-cut running socks in a color similar to your shoes or even fun printed or knee socks can work (depending on the vibe you’re going for). But no scrunching, please.

Show some leg: Revealing a hint of ankle can transform your look and help show off your new shoes. Either wear cropped pants or roll your jeans up an inch or two.

Neutral doesn’t have to mean boring: If you’re looking for one pair of sneakers to wear with everything, you’ll need something relatively neutral. But you don’t have to stick with plain white or black. Leopard print, camouflage, red, blue or even floral can be surprisingly versatile.

Make sure they’re comfy: The whole point of wearing sneakers is making your feet happy. So try on those trainers, and don’t buy them if they don’t fit properly.

Details for top and bottom rows: Pink converse, Forever 21 leopard shoes, purple Sauconys, Mossimo camo sneakers
Lemon Keds, leopard Vans, mint Tigers, Wonder Woman Converse

Linking up with Transatlantic Blonde and Style Elixir’s Style Sessions!