3 Hard-to-Style Shoes for Spring (and How to Style Them!)

The doorbell rings. As soon as you open the door, the clouds hurriedly part and sunlight streams down, illuminating a delivery box. It’s here, it’s finally here!

It, meaning a brand spankin’ new pair of ankle booties—much shorter than your usual mid-calf pairs—bought on a whim to meet a free shipping minimum. Or, maybe it’s the bright sneakers you purchased, partly in hopes of propelling a morning run routine, but mostly due to a sporty-chic Pinterest board-induced daze. It could also be the first-ever pair of oxfords to join your shoe collection, thus sticking out like sore thumbs (ahem, toes) amid a sea of girly ballet flats.

No matter which shoe style patiently awaits, you’ve stepped away from your comfort zone and into uncharted territory. Questions arise: “Are oxfords too masculine?” (No.) “Should sneakers be banished into the confines of the gym?” (Nope.) “OK, if ankle boots aren’t only a passing fad, how can I make sure they flatter my legs and ankles?” (Don’t trip. We got you.)

And the ultimate kicker: “Wait, can I even pull this type of shoe off?” 

With our styling tips for ankle boots, oxfords, and running shoes, we foresee a resounding “yes!” to that last question and of course, plenty of pep in your step.


  • Mix and match. If your sneakers are neon, why not amplify the fun with an animal print? Go bold or go home! However, be careful not to overdo the wild ideas. For example, though the leopard print above is indeed eye-catching, the black-and-white color palette and looser fit of the shift dress help neutralize both the shoes and the print.
  • Dress it up. Because athletic shoes are generally casual, elevate at least one other component of your outfit. Try on fancy baubles with a dress; faux leather leggings with a structured coat; or a jersey wrap skirt with an oversize knit sweater. A quirky approach to balance is essential in making athletic shoes work outside of your weekly jazzercising class.
  • Enjoy the comfort. Honestly, your feet will be grateful. They actually have already sent the fashion gods a nice thank you card for deeming athletic shoes as on-trend.

Dress: ASOS
Shoes: Nike
Necklace: BaubleBar
Silver Bracelet: BaubleBar
Pink Bracelet: Gorjana & Griffin
Rings: Assorted H&M, Nordstrom
Watch: Michael Kors
Crossbody Bag: Marc Jacobs (no longer available)




  • Embrace the masculine/feminine dichotomy. For an androgynous look, pull on a pair of chinos, pants or jeans to go along with the oxfords. If you’d rather offset the oxford’s menswear vibe, add contrast with a short skirt or a demure floral print. We met somewhere in the middle by including a flared skater skirt, but also a button-up Peter Pan collar shirt and a denim vest (made sweet with slight ruffled details).
  • Show a little leg (specifically, the ankle). If you’re reaching for pants instead of a shorter hemline, we’d advise selecting a cropped fit. Another option is simply rolling up or cuffing a longer pair’s hem. Showing a sliver of skin above your oxfords subtly emphasizes a womanly shape, albeit in a modest manner.
  • Experiment with colors, textures and material. Oxfords, also called “brogues,” are traditionally grouped with preppy argyle sweaters, pleated skirts and horn-rimmed glasses. But just like many a Disney teen star, they’ve rebelled and strayed from conventional margins: shiny patent leathers, metallic hues and all-over glitter, to name a few outré variants of the classic oxford. Channel your inner Miley, ladies (but please leave the oversize foam finger at home).

Collar Shirt: ASOS
Oxfords: Target
Necklace: Show Me Your Mumu
Wrap Bracelet: BaubleBar
Denim Vest: Threadsence
Skirt: Tobi (no longer available)
Bag: Nila Anthony



  • Create optical illusions. Doth protest that the ankle boot cuts the leg off at the ankle and subsequently, shortens the leg? If this applies to you, choose a pair that is similar to your skin color (especially when wearing the boots with bare legs), which can noticeably “extend” the leg. Another option is wearing fitted pants (or leggings/tights) with a hem that hits just above or briefly touches the top of the ankle boot, enabling a long, lean, and streamlined look.
  • Accentuate the ankle. If you don’t relate to the above, play up the boot’s namesake: the ankle. The ankle is typically the most slender part of the leg, and highlighting it can be flattering. Like with the oxfords, allow your ankles to peek through with a cuffed or rolled hem when wearing pants. Cuffing or rolling a wide-legged fit may also abbreviate your leg line, so opt for a skinnier fit.
  • Be a show-off! Another reason to avoid wide-legged and baggier bottoms with ankle boots is because the shoe should be in full display—without any fabric in the way. Wearing dresses or skirts is an easy way to underline the style, since boot complements femininity with its more modern, assertive edge. 

Sweater: Local boutique 
White Denim: Nordstrom BP
Necklace: BaubleBar
Wrap Bracelet: BaubleBar
Ankle Boots: Ruche
Rings: Assorted H&M, Nordstrom, BaubleBar
Tote Bag: Cuyana



Do you own any of these shoes styles? Share how you wear the athletic sneaker, the oxford shoe and the ankle boot by commenting below or by uploading a photo on Instagram with the hashtag #TheEverygirl. (We’ll regram our favorites!)