5 Tips on Wearing Sneakers with Jeans & Skirts

Yes, you can wear your sneakers outside of the gym, but there are rules! Okay, okay, I know some are eager to say that it’s just fine to mix the two, your gym shoes and your non-gym sneaks, but really … unless you are in a pinch, there are better choices to make than to wear your stinky running shoes to dinner. When not trying to sweat, take it up a notch with tried-and-true brands (think Nike, New Balance, Converse), since the retro sneaker look is HUGE. And consider some slip-on sneaks, as these may just be your go-to shoe that puts some spring in your step. Whether it’s sneakers with jeans or with skirts and dresses, we have five tips to share so you’ll know how to wear sneakers with jeans … and even skirts!

How to Wear Sneaker with Jeans and Skirts

Tip #1: Cuff those pants (or find jeans that hit right above your ankles) and show your ankle bone.

When wearing sneakers, make them a statement … something to show off. The best way to do that is to make sure they are seen, so your pants need to fall right above your ankle bone. Cuff them, hem them, cut them. Do something to make them that perfect length.

If you’re feeling old school, check out these Nike blazers with a fun neon swoosh. Find these for $100 ASOS. Image: ASOS

Here are a few of our favorite sneakers to pair with cuffed pants or one’s that fall right above the ankle:

Adidas Run 60S 2.0 Shoe

A perfect balance between sporty and casual, these will match almost any outfit. Find these sneakers for $60. Image: Adidas

Fresh Foam Roav Tee Shirt Shoe

Hello, comfort! You can wear these bad boys all day long. Find these for $79.99. Image: New Balance

Rainbow Wave Shoe

Can we talk about fun these are? Pair this with your favorite pair of jeans or dress to complete an outfit. You can find these Rainbow Wave sneakers for $139. Image: Soludos

Tip #2: Don’t wear socks, or at least don’t let them show.

This one can be hard, I know. Especially if you like the espadrille take on your sneaks or slides, as that roping is just not comfy. So find some low-rider socks that don’t show if the thought of naked feet in your closed-in shoes makes you squeamish.

Tip #3: Go for a solid color or classic look.

For most of us, a solid color or maybe just some classic stripes, or a pair of slides with a classic print like leopard, is really all we need. And look at the pictures throughout this article … notice the retro vibe that is consistent with all of these sneakers? Yep, these aren’t your fancy running shoes, but your super comfy, all-day shoes.

Your shoe game just got better with these platform sneakers. Find these for $70. Image: Converse

Here are a few classic and slip-on sneakers:

Grills Grey Suede Shoe

Slip ’em on and head out the door! Find these slip-on sneakers for $84.95. Image: Steve Madden

Vince Camuto Maryenda Slip-On Sneakers

Comfort just got more stylish. Find these Vince Camuto sneakers for $88.95. Image: Nordstrom

Vans Platform

Throw these on with a pair of overalls or white jeans. Find these Vans for $54.95. Image: Nordstrom

Tip #4: Sure, wear them with a dress or skirt, just be careful.

Admittedly, this is almost painful to write, as I just can’t help but conjure up the sight of long skirts, socks, sneakers and fanny packs. But a thoughtful approach to elevate the style of the sneaks and be modern and playful to boot CAN happen. But be careful, okay? It’s harder than it looks to showcase this skirt + sneakers look without looking like a 1980s secretary.

Tip #5: Grab a couple pair and some of those low-rider socks

It’s summer, and there will be times you will welcome not showing off your pedicure, which needs some work. A closed-toe slide or two or a sneak that makes you happy will be a welcome relief from flip-flops and such.

Here are the socks you need:

These no-show socks are ideal when wearing slip-on sneakers or any tennis shoes that hit the ankle bone to ensure they remain unseen. And these have a silicone heel pad so you’ll never have to deal with the frustration of your sock slipping off while walking. This four-pack is $14. Image: Nordstrom

And, our pick? We’re still loving the Nike Cortez, which had a moment in 2016. We’re also loving the Classic Adidas Superstars, which have made a major comeback this past year and the Veja old-school lace-up sneakers with the ever-popular millennial pink pop of color are being styled by bloggers and fashionistas alike. But, pick what you like best and enjoy! Your feet certainly will.

Nike Cortez Basic Shoe