As we continue transitioning from winter into spring, I’ve been looking around for some outfit inspiration. Some wardrobe staples are simply meant to be worn together, such as the classic white t-shirt and jeans look or blazer and loafers. While others rarely meet in one outfit, like cutoffs and a trench coat.
One new pairing I’ve been exploring is skirts and sneakers. The juxtaposition of a typically girly dressier garment with sporty, casual footwear might not seem like it can work, but with the right pairing, you have an outfit formula perfect for your nine-to-five, errand running, or even attending a worship service. Here are a few potential combos to consider.
A classic trainer, like Adidas’ Samba shoe, is a great base for multiple outfits. You can lean into the sporty nature of this sneaker by pairing it with a knee-length or midi pleated skirt, like Macy’s On 34th Women’s Pleated Midi skirt in fiery red or leopard print. Then, throw on a polo sweater like Old Navy’s Polo Sweater in a neutral shade such as “daybreak” or “sea salt,” aka peach and off-white, for a tennis-inspired outfit.
As the weather gets warmer, opt for a short skirt or skort and a polo shirt versus a sweater. Again, check out Macy’s Polo Ralph Lauren shirts in a wide array of colors for a polo to last well beyond this season, and look back to Adidas at their Heritage Tennis Classic skirt that can be worn on and off the court.
Keep on the preppy side of this style by channeling some Nantucket vibes with J.Crew Factory’s City Tour Sneakers in ice blue paired with Loft’s Poplin Pull-On Maxi Pocket Skirt in midnight espresso. For early spring, wear with a button-down and barn jacket such as L.L. Bean’s Adirondack Barn Coat in dark khaki or loden. As we get closer to summer, swap the shirt for a simple tank or Hanes t-shirt, and throw a denim jacket through the handles of your tote bag in case you need the coverage on a warm day.
Speaking of denim, I love pairing it up with leather. For a sneaker and skirt look, you can wear a lace-up shoe like Steve Madden’s Verdict Low Top Sneaker in light blue with a midi to knee-length denim skirt such as Levi’s High Rise A-Line Skirt. Then bring in some leather with Land’s End’s Women’s Leather Jacket in either brown or black. Or, look to your local thrift shop for some oversized leather outerwear for this shoe and skirt pairing. On the flip side, Ann Taylor’s Faux Leather Button Front Pencil skirt will work with a colorful lace-up sneaker and your go-to jean jacket. Of course, you can also wear denim on denim or leather with leather but tread lightly and make sure that either the materials match up in color for a “matching set” feel or contrast enough to feel intentional. Brown leather jacket, black leather skirt, or an indigo wash denim skirt and a lighter chambray button-up.
Another skirt style that lends itself to a sneaker pairing is knit skirts. If you already have a matching knit set, then throw on a chunky sneaker like Dolce Vita’s Daran Wedge Sneaker, which is available at DSW, and walk out the door. If you’re in the market for a knit skirt, then check out Zara’s Basic Knit Midi Skirt in maroon. While there is a somewhat dressy matching top available with this skirt, by all means, add it to your cart. However, I wouldn’t pair this set with a sneaker. Instead, keep the wedge sneaker and midi knit to wear with something a bit more casual, like a sweatshirt you already have in your closet. Or go thrifting for an oversized, perfectly worn, sporty sweatshirt to complete this look.
Another sporty option is a vintage sneaker like Nike’s LD-1000s first released in 1977, with a cargo skirt such as Athleta’s Brooklyn Heights High Rise Cargo Skirt in navy, moss, or black. With a t-shirt, bomber jacket, and ball cap, you have a great outfit for traveling or running to and from soccer practice. Or go with a classic khaki cargo skirt, like Kohl’s Women’s Sonoma Goods for Life Cargo Midi in beige or olive with a striped tee.
For a more chic option to this outfitting formula, consider suede sneakers like TOMS’ Collins Casual Lace-Up in oatmeal or pale rose and a flared midi skirt such as ASTR, the Label’s flared midi available from Nordstrom in black, ecru, or icy blue. Wear with a slim-fit cashmere pullover or a matching knit shell and cardigan for a quiet luxury look suitable for the office or any event in need of laidback elegance.
The last combination to consider, pulled right from my own closet, is a slip skirt and Vans. Yes, slip-on sneakers with a slip skirt for an edgy take to transitional dressing. Vans’ Classic Slip-On Perforated Leather Show in black worn with a Universal Standard slip skit in mossy green. While the shoes are still available, the skirt, alas, is no longer unless you want to scour secondhand retailers. Instead, there’s Quince’s 100% Washable Silk Skirt in forest green. I’ve sported this combination with a turtleneck and tights on chilly days and then no-show socks and a t-shirt for warmer weather. Add a blazer to the first pairing for work and a leather bookbag to the second for being out and about on weekends.
Speaking of socks and tights, I find the key to making any skirt and sneaker pairing functional on these days of chilly mornings and warm afternoons are wearing both. Or starting with tights and changing to socks as the temperature rises during the day. Hopefully you can also find some outfit inspo with the dynamic duo of skirts and sneakers this spring.
