How To Wear Sneakers With A Skirt 0
in Shoes Style

How To Wear Sneakers With A Skirt

How to wear sneakers with a skirt.Like many of you, I have a lot of shoes. As much as I try to pare down my closet and keep my stuff to a minimum, I can’t get rid of any of my shoes (and bags but that’s for a different post). While I relish the times when I have the perfect excuse to pull out my heels with my current lifestyle, it’s just not every day.

I’ve contemplated wearing my Louboutin’s to walk my dog, but I really can’t justify the expense. That being said, the fact that I’m surrounded by heel hating cobblestones is not a bonus either. So it has occurred to me that sneakers might just be the way to go (not to mention most designers have now jumped on the bandwagon and produced some fabulous looking sneakers). Sure, flats work and I like ‘em. I actually have a bunch of really pretty flats, but there are those days when nothing feels as good on your feet as a pair of sneakers. Not only that, but I love to combine styles and sneakers with a skirt is a great example of sporty-chic tomboy meets feminine cool.

how to wear sneakers with a skirt


Make them the stars of the show. Have you walked into a sneaker store lately? I can think of 4 dedicated ones within a 5 minute walk from my place and let me tell you that the range of colours and patterns and designs is insane. From girly mints and pinks to edgy gold details and everything in between, there’s absolutely something for everyone. Find a pair that you secretly love and wear them with a monochromatic outfit. My theory is that if you are going to wear sneakers instead of what’s expected (heels or flats) then you should make them the centerpiece of your outfit.

Let them dress down your outfit. Okay, so you might not be ready to design your outfit around your sneakers, but you can let them work with your outfit. Just like you don’t want your heels to match your bag, you don’t want your sneakers to be too matchy-matchy either. They can, however, be the perfect accent piece. White goes with everything, but so do any eye-catching details like studs or a great animal print.

Go metallic. You already wear jewelry, so why not let your sneakers become the crowning piece of your outfit? From gold to silver to a huge array of metallic shades, find the standout pair and match them to your jewelry.

Go for the classics. There are some sneakers like converse or vans that are so widely accepted that you can pretty much wear them with anything. Since they are relatively streamlined and sleek, you can pretty much wear them with everything. Simply put, they have the cool factor and are easy to wear.

Choose vintage. Pretty much every company I can think of is coming out with a version of their vintage shoes, from New Balance to Nike to Reebok to Adidas, they’re all doing it. The truth is that these shoes kind of work because they evoke nostalgia, take us back to our childhoods and look pretty cool with a pencil skirt (try it in leather) or a midi skirt.

how to wear sneakers with a skirt


  • Opt for a wedge sneaker or a pastel shade or even a fun print to keep you looking feminine.
  • Throw on a menswear inspired vest on to balance out the casual factor of your sneakers.
  • If you want a more streamlined look then aim for slip-ons rather than lace up shoes.
  • Basic fashion rules like proportions and contrasts still matter. Pair a chunky knit dress with a pair of simple white sneakers.
  • A sleek pencil skirt with matching sneakers will look more formal than a flirty skirt worn with Chuck Taylors.
  • A minimalist pair of sneakers paired with floaty, airy fabrics will give you a more feminine look.

Most of all, don’t be afraid to try out this trend. Ease yourself in by matching your sneaker to your skirt, you’ll have a more refined look and they won’t be as eye catching. Remember, opposites attract and with this trend you’ll be super comfortable and just maybe it will push you a little outside of your comfort zone.


Read: How To Style Sneakers for more tips.

Do you wear sneakers with your skirts?

Continue the conversation on INSTAGRAM and BLOGLOVIN


images courtesy of DollarPhotoClub



Caroline has worked with international designers in fashion retail and completed professional makeup courses when working in the beauty industry. Her love of writing, photography and film inspired her to work at the Canadian Film Center and then to earn a BFA in Screenwriting. In addition to her blog, Style On The Side, you can see her work in Huffington Post Canada and other international websites.

Latest posts by caroline (see all)

You Might Also Like

Stay Healthy And In Style In Las Vegas

Jewelry Every Woman Should Own

How To Dress Just For You

Designer Spotlight SYCAMAW

Style: London Fashion Week

Must Have Statement Jewelry Fall 2014

What Your Jewelry Says About You

Summer Solstice In Style

What To Pack For A Mini Getaway

How To Dress An Apple Shape

Fall Outfits That Will Always Work

Best Accessories For Fall

How To Wear Green 2013

How To Style Chunky Sweaters

How To Wear A Summer Scarf

What To Wear At The Pool

How To Wear Athleisure

How To Choose The Perfect Heels

Best Hat For Your Face Shape

Best Dresses For Summer At Fine Finds

Luxury in Style: September Celebrations

How To Store Winter Clothing

How To Wear Summer Whites

Packing For Two Weeks In Europe

How To Wear An Oversized Tshirt

How To Travel With Your Jewelry

How To Wear Yellow

How To Wear Fringe For Fall 2014

When It’s Too Hot To Pick An Outfit

The Eternity of Diamonds

How To Wear Mixed Metal Jewelry

How Where You Live Influences Your Style

Your Ultimate Wardrobe Color Guide

How To Wear Silver Jewelry In Style

How To Be Comfortable And Stylish

Where to find Modern Artisan Jewelry

What Your Hat Says About You

Ultimate Guide To Layering

How To Add Colour To Your Wardrobe

How To Dress Up A Boring Outfit

Best shoes for traveling in Europe

British Mode June Edition

Vintage Shopping In Berlin

Why You Have Nothing To Wear

How To Look Effortlessly Chic

Why Is Style So Important

How To Pack For A Weekend Getaway

How To Effortlessly Reinvent Your Style

Eyeglasses For Everyone: Warby Parker

Granville Island Artists

How To Be Casual But Stylish

How To Wear Gold Jewelry

How to Wear Mint

How To Wear Green For Spring 2015

Look great this summer without being a hot mess

Shopping In Portland Accessory Style

How To Style A Denim Jacket

Is It Okay To Wear Nude Tights

How To Feel Beautiful

Wedding Sparkle in Style

How To Dress In Your 30s

What Your Sunglasses Say About You

How To Wear Plaid For Fall

What To Wear On A Boat

7 Bags Every Woman Should Own

How To Look Good In Tights

Be Stylish Not Fashionable Or Trendy

The Color Guide

Best Winter Accessories

What Clothes You Should Splurge On

Summer Dresses In Style

Gift Guide For The Fashionista

Best Summer Bag For Everyday 2014

Style Shopping at Fine Finds

Fly And Fierce Boutique

How To Dress For Canada Day

How To Style Flats

How Style Affects Our Confidence

How To Wear Sequins For Day

Must Have Accessories For Fall

How To Wear Boots For Spring

This Ain’t California: Skateboarding Fashion

How To Wear Dresses For Fall

Off Duty Style

8 Tips For Packing Light

How To Dress A Pear Shape

All About Spring In Style

How To Add Prints To Your Wardrobe

How To Find Your Style

Glasses: Blink and you’ll See!

How To Look Less Frumpy

Style For Research: Fascinator

Best 2016 Runway Shoe Trends

Beret: A Hat For All Seasons

Best Coats For Spring 2015

Best outfits for winter travel

Shoe Closet: A Peek Inside

Summer Dressing Guide

Fashion Flashback Styles of 2013

How To Wear Pink For Fall

Travel Style And Life

Today We Wear Black

Designer Spotlight Darylynn Eyewear

Arm Candy Show Off Your Bracelets

Spring Shopping List

How To Choose The Right Accessories

Consulting For Online Success

British MODE: January Issue

How To Style Jewelry

How to Run in Heels

Statement Earrings Guest Post

Style: Lazy Summer Days

How To Love Your Clothes When You Don’t

How To Wear A Moto Jacket

How To Style A Polka Dot Dress

How To Add 50s Style To Your Wardrobe

Fashion Picks For November 2014

How To Add The 60s To Your Style

Style Habits That Make You Look Older

Summer Office Style

Classic Pieces Every Woman Should Own

Best Sweater For Your Body Type

Style Picks For February 2015

Should You Have A Minimalist Wardrobe

Designer Spotlight Standfor Shoes

How To Wear Ankle Boots

Fedora: Traveling In Style

How To Pull Off Hats

How To Keep Your Clothes Looking New

Photography For Bloggers Composition

How To Dress Vintage Modern

Clothing Tips Every Woman Should Know

Must Have Coats For Fall

Navy Heels With A Touch Of Gold

I Want To Be Her: Book Review

Black… And the Colour is Gone…

Sunday Musings In Style

Best Pants For Your Body Type

Essential Accessories For Men

Designer Spotlight Konplott Jewellery

Portland Shopping Garnish Apparel

Writing Inspiration

What To Wear When You Have Nothing To Wear

Designer Spotlight Quinoa Paris

Fashion Of Anime Cosplay

How To Update Your Wardrobe

How To Make Clothes Look Expensive

Best Sunglasses For Your Face Shape

How To Choose The Bag For You

Links I Love

British Fashion: How Do You Define It?

How To Wear Scarves In Style

How To Choose The Best Running Shoes

Designer Spotlight Talk To My Shoes

How To Style A T-Shirt

How To Dress In Your 40s

How To Make An Old Coat New Again

How To Shop For investment Pieces

How To Make Heels Comfortable

How To Add The 70s To Your Style

Dance Inspired Wardrobe

How To Wear A Tshirt

How To Take Great Photographs For Bloggers

Effortless Style And Beauty

My Story In Brief

How To Wear And Care For Velvet

British MODE December Issue

The Truth About Heels

Shoes Every Woman Should Own

How To Make Your Legs Look Longer

How To Succeed Online Part 3

How To Add Colour To Your Fall Wardrobe

Must Have Hats For Fall 2014

How To Style A Fuchsia Dress

Odd Pears Why Socks Matter

Hair Accessories: Hair Raising Tale

How To Wear Red 2013

Jewelry: Salt Spring Island Style

Vintage Bags In Style

Contemporary Fashion Georgie And Elaine

How To Take Your Look From Day To Night

How To Dress An Inverted Triangle

Military Inspired Style For Spring 2015

How To Be Modern Gothic and Rocker Chic

How To Feel Good About Your Style

How To Determine Your Body Shape

Branding And Images

On Our Radar March 2015

Polette Parisian Eyewear

November Favourites

10 Creative Ways To Style Up Your Office Outfit

Top Summer Essentials 2014

Must Have Spring Accessories

How To Layer Clothes For Fall

How To Dress When You Work From Home

How To Shop For Vintage Clothing And Bags

How To Wear High Heels Without Pain

9 Accessories Every Woman Should Own

National Hat Day 2014

What Is The Deal With Loving Your Body

Best Jeans For Your Body Type

How To Buy Pants That Fit

Style: British MODE

How To Dress For A Work Party

How To Wear Orange Spring 2014

How To Wear Black

How to Walk in Heels In Style

What To Wear On A Plane To Europe

Interior Design: Style On The Side

Fashion Is Art In Portland

Style On The Road

Sidewalk Sale Shopping in Style

How To Travel In Style

Date Night Essentials

Coach Bag Is Art: Style

Must Have Statement Pieces

Womens Essential Checklist

Am I Too Old To Wear That

How To Dress A Ruler Shape

Which Type Of Tourist Are You

Ankle Boots Were Made For Walking

Top 5 Style Posts Of 2015

Makeup Pouches In Style

How To Mix Prints In Style

How To Style Sneakers

How To Wear Navy In Style

How To Buy Pearls

How To Take Your Wardrobe From Winter To Spring

European Style And Travel

Designer Spotlight Work Wonders

Best Gifts For The Fashion Lover

How To Style Hats For Fall 2014

Styling Tricks Every Woman Should Know

How To Choose A Leather Handbag

Blogger Love

What To Pack For A Long Flight

Dresses Every Woman Should Own

How To Wear Flowers In Your Hair

How To Wear Hats In Fall 2016

New Year: A Wonderful 2014 To All

British MODE: Haute Couture

What To Wear To An Interview

One Dress Three Weddings

How To Be Elegant Every Day

White For Fall In Style

What Your Bag Says About You

How To Succeed Online Part 2

How To Dress For Winter

Your Shoe Wearing Guide

Where To Shop For Vintage And Designer Apparel

October Fashion Beauty And Fitness Picks

How To Wear White After Labour Day

How To Wear Pink

How To Wear Purple 2013

Unique Jewelry Fabulous Accessories

Shopping FAQ In Style

How To Buy The Best Running Shoes

Why You Should Dress For Yourself

Designer Spotlight Best of 2014

How I Lost My Style

How To Succeed Online Part 1

Fashion Must Haves For January 2015

Your Go To Outfits At Any Age

Blogging And Living Abroad

Designer Spotlight Blackbird London

December Style Picks 2014

Make 2016 Your Most Stylish Year

Designer Spotlight Perfect Black Leggings

What Your Watch Says About You

Hit The Gym In Style

How To Wear White

How To Wear Cufflinks

Best Jewelry For Summer 2014

Long Evening Dresses

Best Way To Wear Sweaters This Fall

Designer Spotlight EverywhereUR

Monogram Jewelry In Style

How To Grow Your Blog With Pinterest

How To Look Chic At The Office

Everyday Bag Essentials

Fashion And Architecture

Ultimate Accessories Guide For Major Social Events

Buying Jewellery: Must Read Tips

How To Wear Brown

Stories From The Road in Style

How To Find The Perfect Party Dress

Essential Wardrobe Checklist For Men

Patches of Denim

Summer Road Trip In Style

Shopping For Court Shoes

Easy Rules To Looking Your Best

How To Dress For Summer

Designer Spotlight Femi Pleasure

Your 8 Rules To Shopping

Best Beauty Products For Spring 2015

Best Shoes For Travel

Crystals For Winter In Style

Cocktail Fashion: Drink, Dress and Ring

How To Wear Pastels Spring 2015

Shoe Shopping In Madrid

Pre-Loved: A Treasure Hunt At Holy Rags

How To Add 40s Style To Your Wardrobe

Best Bags For Summer Sightseeing

How To Wear Gray

The Bespoke Tailor: A History Of Style

Style Stories Louboutin Heels

The Nutcracker

Are Sandals Bad For Your Feet

How To Be Modern Boho

How To Dress An Hourglass Shape

Fashion Rings For Style


  1. Great post! I love the bit about metallic sneakers, I have a gold pair and a silver pair that I usually feel a little “Beyonce” wearing and style them carefully but I like the idea of throwing an a-line midi into the mix. And as for classic shoes… yup, still obsessed with my Adidas (but honeslty, who was ever over them?) and wearing them left, right, and center!

    1. The more I wear them the more I love sneakers! I’m dying for a metallic pair now….

Comments are closed.