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.
9 Midi-Skirt-and-Shoe Combos You Should Copy Immediately
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.
Branch out from black with this chocolate-hued thong sandal, grounded with a sculpted kitten heel.
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.
Monogrammed, leather-trimmed and finished with a polished horsebit fastening, this is our kind of practical tote.
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.
We love a midi skirt in crisp poplin. This one is lined in cotton, too, for breathability.
Loved by Bella Hadid and Charli XCX, Vivaia is a go-to for comfy but cool sneakerinas to wear on repeat.
Le Specs is up there with the best affordable sunglasses brands.
Khaite's Lotus tote gets a raffia makeover.
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.
Trust Balenciaga to put a futuristic riff on Scholl's iconic clogs.
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.
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.
The cargo skirt is back. Tap into the trend with workwear-inspired fabrics and utilitarian details like drawstrings, bunjee cords and pockets.
Reformation's shoes are impeccable quality. And by investing in a wedge, you'll get all the height without the discomfort.
Erdem has the unique knack of making traditionally twee items feel off-kilter, like with the frayed appliqué detailing on this cardigan.
Offset a utilitarian look with something unabashedly playful like this rainbow beaded bag.
5. Ballerinas
Style Notes: I know what you’re thinking, ‘aren’t ballerinas and midi skirts too girlish to be cool?’. The key to pulling off this combo: go for a flat with edge. A high vamp, a sporty sole, mesh or laser-cut uppers – or, for top marks, the cult split-toe Tabi made famous by Margiela in the ‘90s.
There's a few canonical designer pieces that will never date and Margiela's iconic Tabis are obviously well worth the investment.
Classic but bang on-trend, a bold monochrome polka dot is a failsafe choice this summer.
M&S' jersey track jacket has been a serious hit this summer (the red is long sold out), so add it to basket while you still can.
Jimmy Fairly just collaborated with cult British jewellery brand Missoma on a glam range of sunnies complete with gold-vermeil accents.
6. Slingbacks and Socks
Style Notes: For those who love the ladylike charm of a full-skirted silhouette and heels, there’s a fresh way to style this duo for spring/summer 2026. Simply add a sheer sock to your slingback shoes and you’re tapping into that magical Miuccia Prada paradigm; a look the first lady of fashion invented back in the ‘90s, where conservative silhouettes are somehow styled into something sporty and futuristic. Don’t ask me why, it just works.
These white patent slingbacks are one of the few things left from H&M's collab with Stella McCartney, so snap them up while you still can.
The easiest way to upgrade your existing footwear collection is with a sporty-but-sultry sheer sock.
Mango gives the circle skirt a contemporary feel with pockets, pleating and a low-rise waist.
If you love to wear long sleeves even come summer, invest in a few sheer-knit basics and underpin with a tonal bra.
7. Block Heel Pumps
Style Notes: Staple wardrobe queens will be looking for something a little less directional to wear with their midi skirt, and we can confirm a block heeled pump is a worthy investment. A canonical designer take from Bottega, Gucci and Roger Vivier is always smart, but for a spring/summer 2026 twist look to something with a high vamp like Ami Paris’s take, or Marks & Spencer’s affordable pair below.
M&S I applaud you for the impeccable glove shape of this shoe.
There's a timelessness to a top-handle bag, a ladylike style that can be worn day or night.
Fringing is the fun micro-trend taking over this summer.
With the rise of '80s-inspired silhouettes, it was only a matter of time before the batwing sleeve made its comeback.
8. Wedges
Style Notes: Another ugly shoe coming in strong for spring/summer 2026 is a surprise even to us at WWW: the pump wedge. If you’re really not down with an ‘08 classic you saw women wearing to the office, dip your toe in with a cool mule (look to Le Monde Béryl and Topshop) or opt for a sculptural heel à la Toteme. Extra points for wearing this shoe with the style set's favourite awkward-length skirt.
Trust Toteme to make this divisive shoe trend look so elegant. These croc-effect leather pumps are set on a 2-inch wedge heel and finished with a pointed toe.
A lace-trimmed slip has become a bit of a wardrobe staple recently.
Those in-the-know are swapping neutral accessories for brightly coloured handbags like this hot-pink vintage Chanel.
You can always rely on The White Company to nail wardrobe basics.
9. High-vamp Pumps
Style Notes: No fashion bunny could ever forget the moment when then-creative director Phoebe Philo sent a procession of glove shoes down the spring/summer 2015 Céline catwalk. And whether thanks to the 2026 obsession with 2016, or the ballet flat’s stronghold on footwear trends for the past few years, we’re witnessing a renaissance right now. This sportier take on a ladylike silhouette will freshen up even the simplest of outfits, as Anne-Laure Marais proves with this hank top and slip skirt combo.
French brand Souer knows how to put a directional spin on wardrobe staples — check out the high vamp on these simple black ballerinas.
With Nothing Underneath has expanded beyond its USP of shirts and shorts recently and we're not mad about it. This linen slip skirt is impeccably cut.
Much like most of Ref's catnip collection, this handkerchief top is brimming with '90s nostalgia – but the lustrous silk-satin adds a grown-up edge.
Simple summer outfits look so much better with the addition of statement jewellery. Forget minimalist gold chains and opt for a standout resin cuff instead.