Classic Sneaker Style.

Classic Sneaker Style

Created in partnership with DSW + ShopStyle.

Maybe I have been living under a rock, but something I didn’t know until more recently is that DSW has the absolute cutest classic and fun sneakers! From comfy slip ons to versatile white sneaks to more fun colorful sneakers like this red pair and this pink pair, they have a pretty amazing assortment. Today I am styling two different pairs (+ I’ve also rounded up ten super fun options in the collage below).

Classic Sneaker Style

The outfit above is my go-to everyday running errands, want to be comfy but cute look. Charleston is a small town and you can’t really wear sweatpants and be anonymous the way I could in New York. This is a good, comfortable alternative: a chunky cashmere sweater, a camel coat, shiny leggings (these are also from DSW), and cute sneakers. Easy and breezy and perfect for running around.

PS – Right now, DSW is running a Luxury Pricing Event  that has promotions up to 65% off through 1/24!

Classic Sneaker Style - DSW sneakers

Classic Sneaker Style Classic Sneakers and slip-ons

shop the collage: one (just about sold out, shop more Nike styles here!) // two // three // four // five // six // seven // eight // nine // ten

DSW Reebok sneakers Classic Sneaker Style

My friend Molly always looks so chic and put together and one of her go-to looks is a longer dress and sneakers (note: this is definitely a Charleston specific kind of look as we can get away with skipping tights right now if we wear a long dress… back in Brooklyn I would have had to wear tights which wouldn’t be as cute).

I really love how this grey pair from New Balance complements my dress! This pair is so versatile – they look great with jeans, leggings, dresses, pretty much everything!

long dress and sneakers outfit winter casual outfit winter outfit with classic sneakers long dress and sneakers fashion long dress winter outfit

photography by Laura Saur.

Leave a Comment


  1. Casey B says 1.19.22

    I am so happy sneakers and dresses are a thing! I especially love New Balances right now!

    • grace at the stripe says 1.19.22

      Me too! So comfy and easy!

  2. Steph P says 1.19.22

    Cute! Do you have favorite no-show socks that actually stay up?

    • grace at the stripe says 1.19.22

      Hi! I don’t…. I do Bombas for workouts but if I’m doing non sweaty activities I tend to skip socks. This will likely gross some people out but my feet don’t get very sweaty so I don’t really care!

    • Sara says 1.19.22

      Hi Steph! I had to chime in on the no show socks. I’ve tried a million and these are my favorite: The come up a little bit higher than most, so they stay put better. They don’t work great for slip on sneakers, but any lace up ones they are amazing!

      • grace at the stripe says 1.19.22

        Oh now I’m intrigued – just ordered these, thank you for the rec!

  3. Susannah says 1.19.22

    I am confused, you are constantly talking about how you never wear sneakers, just the Vince ones

    • grace at the stripe says 1.19.22

      That was true maybe a few years ago? I haven’t said that in a while. I wear sneakers a lot and have had a lot of outfits wearing sneakers. The Vince pair was definitely the gateway drug!

  4. mary says 1.19.22

    I love new sneakers and I love DSW. It’s so easy to pop in and try on different styles and sizes myself rather than waiting for a salesperson to lace me up. Introverts, amirite? I’m wearing a super comfortable pair of Brooks running shoes I bought at DSW as we speak.

    • grace at the stripe says 1.19.22

      I could not agree more. I hate having a sales person lace me up, so awkward!

  5. Brianna Rooney says 1.19.22

    these are what I call my walking to work sneakers – not chunky workout ones but cute enough and I ALWAYS buy them at DSW! my go to

    • grace at the stripe says 1.19.22

      Yes! The perfect in between sneaker. Comfy and cute <3

  6. Sara says 1.19.22

    Well Grace, now I NEED the white Reeboks! That little bit of green is delightful. How did you find them to be size wise? Are they comfy?

    • grace at the stripe says 1.19.22

      Hi Sara! I found them to be true to size and super comfortable. I have narrow feet so they’re a little wide but I just laced them up tightly. Would highly recommend (and agree on that little bit of green!). xx

  7. Stacey says 1.19.22

    I’m loving the movement to wear sneakers with more than just workout attire. I wear my different sneakers with everything. A favorite are a pair of sorels, they are super cute and waterproof!

    • grace at the stripe says 1.19.22

      I agree! It certainly makes things easier and more comfy!

  8. Ana says 1.19.22

    OMG Grace, I love these! That first look is my jam, I feel very inspired!

    • grace at the stripe says 1.19.22

      I am so glad – thank you!

  9. Rachel says 1.19.22

    I love sneakers! But for some reason just can’t get behind all white ones, but I just bought those reebok ones in gold! So fun, and comfy! Love all these options!

    • grace at the stripe says 1.19.22

      All white took me a little while to get used to but once I did, I love the look. But I totally get it. Gold sounds so fun!!!

  10. Beka says 1.19.22

    LOVE sneaks and dresses. My jam in high school was a denim skirt and a pair of adidas classic shoe. This fall, I went with my son and friends for pre-dance pictures, not a single girl had a heel on. They all opted for adorable fur look slippers or fun sneakers to go along with their beautiful dresses and jumpsuits. Totally worked.

    • grace at the stripe says 1.20.22

      Love that!!!

  11. Cara says 1.19.22

    I’ve really taken to wearing sneakers all the time with everything the past couple of years and I need to add those grey new balance to my collection.

    • grace at the stripe says 1.20.22

      They are so good!!!

  12. Stephanie says 1.20.22

    Hi Grace,

    Love this look! Is the cardigan the same one you posted about from Amazon? If so, I’m buying now 🙂

    • grace at the stripe says 1.20.22

      HI! No, this is a coat not a cardigan… they are the same color but are actually super different. This one is from Theory!

  13. Michelle L says 1.21.22

    So cute! I’m loving the sneaker trend. Do you have outfit details listed somewhere for the white sweater? I love the v-neck & side-slits.

    • grace at the stripe says 1.21.22

      Hi Michelle! Thank you 🙂 It’s from Lisa Yang, from Hampden Clothing here in Charleston! Her cashmere is SO SOFT.

  14. Marianne says 1.25.22

    Love the white sneaker outfit–especially that great coat! Do you have outfit details?

    • grace at the stripe says 1.26.22

      Yes! The coat is from Theory – here is a link!

      Sweater is from Lisa Yang and leggings are DSW.

      • Marianne says 1.26.22

        Thank you!!

  15. Sunny says 2.22.22

    I love your style and this post especially for mixing dresses and sneakers! But could you tell us where the coat is from? It’s such a perfect topper!