9 Midi Skirt And Shoe Outfits To Try Immediately
In 2026, when capri pants and balloon trousers are reigning supreme, it’s easy to forget the trusty staples that have seen you through years of chic outfits. I get it: you want to look on-trend, but that doesn’t mean you have to cast aside your wardrobe mainstays as soon as something new and shiny comes along. I’ll never forget the moment Alessandro Michele made the midi skirt a "thing" again. The then-creative director of Gucci sent a gold sunray-pleated design down the autumn/winter 2015 runway, and my world spun. We’d all been wearing spray-on jeans for the past decade, and suddenly, this unabashed femininity felt bold. It paved the way for the return of skirts, and I, for one, haven't stopped revelling in the revival.
When noughties trends started creeping back in, I found myself worrying about the connotations of my old midi skirts if I dug them out again. Was it—whisper it—"frumpy" to wear such a thing? Did I need to invest in a low-rise, maybe drop-waisted version, or just forget it altogether? Then I checked myself. Obviously, no one who has witnessed the merry-go-round of trends (after a decade working as a fashion editor) and cares about the planet should ever throw away a decent item of clothing that they enjoy wearing.
The key to bringing your staples up to date? It is all in the styling, and right now, we’re focusing on shoes. From sneakerinas and wedge flip-flops to split-toe flats and high-vamp pumps, here are nine trending shoe styles to wear with your trusty midi skirt this season.
Latest Videos From
1. Toe-Post Kitten Heels
Style Notes: We have the '90s to thank for the embellished midi skirt. A microtrend that’s recently resurfaced, it’s typically a pencil cut (anything full would look too much like occasionwear), and sheer to showcase the detailing. To keep things casual, style yours with an easy tank top and this season’s favourite kitten-heel thong sandal à la Aimee Song.
ASOS Design
Havana Toe Thong Kitten Heel Sandals
Branch out from black with this chocolate-hued thong sandal, grounded with a sculpted kitten heel.
ASOS Design
Scattered Embellished Mesh Maxi Skirt in Cream
The embellished skirt is more versatile than you might first think. You can definitely dress this one down with a tank top and the right shoes.
Gucci
Mercato Medium Tote Bag
Monogrammed, leather-trimmed and finished with a polished horsebit fastening, this is our kind of practical tote.
Boden
Ribbed Cotton Vest in White
A tank top has the ability to make just about anything (yes, even a sparkly midi skirt) look low-key.
2. Sneakerinas
Style Notes: Whilst I admit to Googling Lily Allen’s OG Nikes-and-dress combos since West End Girl dropped last year, I'm still not ready to revisit trainers with midi hemlines. If you want a comfy option though, try a sporty sneakerina to ground your daytime skirt.
Mint Velvet
White Cotton Full Midi Skirt
We love a midi skirt in crisp poplin. This one is lined in cotton, too, for breathability.
Vivaia
Square-Toe Hybrid Mesh Mary Janes
Loved by Bella Hadid and Charli XCX, Vivaia is a go-to for comfy but cool sneakerinas to wear on repeat.
LE SPECS
Pilferer Rectangular Ecozen Sunglasses
Le Specs is up there with the best affordable sunglasses brands.
KHAITE
Lotus Medium Raffia Tote
3. Y2K Mules
Style Notes: We’re knee-deep in a noughties renaissance, so, naturally, the Y2K mule is back (I've been deep-searching Ravel and Faith styles on Vinted recently). If you’re a minimalist at heart, just pick one feature – a cork sole or buckled strap – to tap into the trend, while enthusiasts might even plump for diamanté embellishments or logo hardware. Pernille Teisbaek snapped up the coveted Balenciaga x Scholl design and styled it with a low-rise cargo skirt at Milan Design Week.
Balenciaga X Scholl
Heeled Sandals
Trust Balenciaga to put a futuristic riff on Scholl's iconic clogs.
Cotton On
Ruffle Knit Cardi in Black
We love a Nineties inspired cardi top at WWW.
This cargo skirt is one of my favourite pieces from Victoria Beckham's collaboration with GAP.
DeMellier
The Small Hudson | Black Small Grain
Everyone one needs a LBB (a little black bag) in their repertoire.
4. Wedge Flip Flops
Style Notes: Another Y2K favourite that’s crept back in this season is the wedge flip flop, in all of its ugly glory. You can go full Spice Girls with a statement foam platform or lean into the minimalist side of this era with barely-there straps and a low sliver of wedge. Once you invest, you’ll see how transformative the ‘wrong’ shoe can be to an outfit you thought you were long tired of.
