Styling Skirts with Sneakers

This post is sponsored by Zappos.

Chicago fashion and lifestyle blogger Jessica Sturdy of Bows & Sequins styling an animal print midi skirt with white leather sneakers on Oak Street in the Gold Coast.

The other day I was thinking about why I have an affinity for styling sneakers with skirts and dresses… Sure, they’re so much more comfortable than most sandals and heels and make walking around the city a breeze, but that’s not usually my thought process when I reach for a cute pair of tennis shoes when I’m getting dressed. I got to thinking maybe it’s deep-rooted from my cheerleading days, seeing as grades in 6th through 12th, I was always wearing a classic pair of white sneakers with my skirt (and bloomers) as a part of our uniforms. (You know I love any excuse to get all psychology about a topic that doesn’t even warrant a deep dive… 🤪)

Fashion blogger Jessica Rose Sturdy of Bows & Sequins styling a white button down shirt with a silk leopard midi skirt and white sneakers.

Cognitive behaviors aside, I’m all about juxtaposition… I like to throw a little curveball when I’m styling an outfit, a little something unexpected. This outfit would look just as cute with a pair of pumps or a strappy pair of sandals (and there’s a time and a place for both), but I absolutely love it with a classic pair of bright white sneakers.

Fashion blogger Bows & Sequins styling the Keds White Leather Ace Sneakers with a leopard skirt.

I just got these leather Keds sneakers from Zappos to replace my worn out wear-with-everything sneakers and I am obsessed with them! I love the low profile, I love the clean all-white look without any lines or logos, and I absolutely love how comfortable they are. I think I let out a little gasp when I put them on the first time… I was definitely not expecting the foam footbed to be so cloud-like!

Fashion and lifestyle influencer Jessica Rose Sturdy wearing a cropped white shirt with a leopard skirt and white tennis shoes for work.

If you, too, love the look of these sneakers, you can have them by early next week! I order most of my shoes from Zappos because of their free shipping that’s fast AF. (Free returns for 365 days, too!) By now, you guys probably know that I tend to err on the side of last minute… Usually right before a trip or before a shoot that I have, I’ll remember something that I forgot to order a few days earlier and it’s Zappos to the rescue. At checkout, you get a guaranteed delivery date and (at least in Chicago) it’s usually one business day FOR FREE. Can’t beat that!

Fashion blogger Bows & Sequins styling classic white Keds sneakers.

But back to styling these sneakers with skirts! My number one tip? Don’t overthink it. I’ll always hear “but I can’t pull that off.” You can, my friend, you totally can! To start simple, pull out a printed skirt from your closet. Then, take a basic white tee or a classic button down shirt and tie it up. You could also tuck it in, but I’m all for the tie lately, as I think it looks a bit more fresh. Lastly, just slip on this pair of leather Keds and you’re out the door! Easy peasy.

Or if you’re wearing a cute denim skirt, just pair it with a graphic tee and sneakers. And the next time you throw on a dress for brunch on the weekend, try it with sneakers instead of your go-to sandals. I’m telling you, this style of Keds goes with absolutely everything! (And they fit true-to-size, too!)

Chicago fashion blogger Jessica Sturdy of Bows & Sequins styling a leopard print silk midi skirt.

Shop the Outfit…

Sanctuary Animal Print Midi Skirt
Vineyard Vines White Button Down Shirt
Keds Ace Leather Sneakers
Prive Revaux Sunglasses
Kate Spade Watch
Black Zippered Clutch
YSL Shine Lipstick in Rouge Ballet

Chicago beauty blogger Bows & Sequins with messy blonde hair wearing Prive Revaux sunglasses.

Fashion and style blogger Jessica Rose Sturdy styling a leopard midi skirt with a white oxford shirt and classic white tennis shoes.

Bows & Sequins wearing the all white leather Keds Ace sneakers.

Fashion and lifestyle influencer Bows & Sequins styling a leopard midi skirt with a white button front shirt and sneakers.

Fashion and outfit blogger Bows & Sequins styling a tied-up Vineyard Vines collared shirt with a leopard pencil skirt.

Top Chicago blogger Jessica Sturdy of Bows & Sequins styling a leopard midi skirt with white sneakers.

Fashion blogger Bows & Sequins styling the all white Keds Ace sneaker with an animal print midi skirt.

Chicago wellness blogger Bows & Sequins wearing a white collared skirt with a leopard skirt.

Chicago blogger Jessica Sturdy of Bows & Sequins wearing a white collared shirt with a leopard skirt.

Jessica Sturdy of Bows & Sequins on Oak Street in Chicago's Gold Coast wearing a leopard skirt and white sneakers.

Chicago blogger Bows & Sequins wearing the Keds Ace sneakers in all white leather with a cheetah midi skirt.

Chicago lifestyle blogger Jessica Sturdy of Bows & Sequins styling a leopard skirt with white sneakers for a cute workwear look.

Fashion blogger styling an outfit with Keds sneakers and a leopard skirt.

Chicago style blogger Bows & Sequins wearing a Vineyard Vines shirt with an animal print skirt.

Chicago lifestyle blogger Jessica Rose Sturdy styling a leopard print midi skirt with a white collared shirt and tennis shoes.

Chicago fashion influencer Bows & Sequins wearing all white sneakers from Keds with an animal print skirt.

Fashion and lifestyle influencer Bows & Sequins styling Keds sneakers.

Leave a Comment

13 Comments

  1. 5.31.19
    Sam commented:

    Love this look! So fun for spring/summer!

    xx
    Sam

    • 6.1.19
      Jessica commented:

      Thanks Sam! I have a feeling I’ll be swapping the collared shirt for a simple white tee and wearing this on repeat all summer long.

  2. 5.31.19
    Meg commented:

    Love this whole look! I also like wearing tennis shoes with dresses (maybe its because I was a baton twirler for 7 years? and we wore white tennis shoes with our parade costumes?)
    Meg
    http://www.deposanddemos.com

    • 6.1.19
      Jessica commented:

      Wait a seconddddd… I used to twirl baton, too!! Alllllll of the white sneaks (that I’m pretty sure were the classic Keds) I’ve literally never met anyone else that had all of the bizarre hobbies I did as a kid. People are usually like, wait, you did what??

  3. 5.31.19
    Cynthia commented:

    Very cute

    • 6.1.19
      Jessica commented:

      Thanks Cynthia! xx

  4. 5.31.19
    Missy May commented:

    My kind of outfit right here. Great casual chic outfit. That skirt is everything.

    https://www.missymayification.co.uk

    • 6.1.19
      Jessica commented:

      So fun, right?! I know this skirt is going to be on weekly repeat all summer long. So many ways to wear it! xx

  5. 6.3.19
    Michelle commented:

    LOVE LOVE LOVE this outfit!!! xx

  6. 6.9.19
    Jenny A commented:

    Super cute! I’ve been looking for a pair of white sneakers like this recently. Do you wear your sneakers with no show socks? Thanks – Jenny A

  7. 6.16.19

    I am usually not a fan of sneakers with a skirt or dress, but you are rocking this look. It is very cute and casual. I think it am just so obsessed over the skirt though. I do think this would look amazing with heels for a work day look!