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I’ve Done the Research—These Are the Flat Shoes That Look Chicest With Leggings

By Swedan Margen

I’ve Done the Research—These Are the Flat Shoes That Look Chicest With Leggings

You'd have to be living under a rock not to realise that, since Covid, leggings have reclaimed their place as a go-to wardrobe staple—not just as activewear or loungewear, but as a chic, versatile option for various events, from errand-running to dinner outfits.

Naturally, the key to making them feel considered rather than casual lies in the shoes you pair them with. For me, an everyday flat offers proper support, stays beautifully blister-free and still looks chic enough to elevate even the simplest of leggings outfits. You can save stilettos and kitten heels for evening plans—for now, it’s all about reaching for those reliable flat shoes that work seamlessly with your favourite leggings.

The right pairing can completely transform the look. Whether it’s pointed-toe flats for a polished feel, football trainers for a trend-led edge, or even flip flops on those unexpectedly warm days, there are multiple combinations to complement your leggings of choice. Read on to discover the three flat shoes I'll be wearing on rotation with leggings this spring.

3 Flat Shoes I'm Pairing With Leggings This Spring:

1. Pointed-Toe Flats

All black outfit with pointed toe shoes.

Style Notes: A pointed-toe flat instantly elevates an otherwise casual outfit, giving it a more refined and sophisticated feel. Its sharp silhouette adds poise and signals confidence and intent.

Shop the Look:

Women's Vittoria Ballerina

Gucci

Women's Vittoria Ballerina

The signature GUCCI buckle is understated yet instantly recognisable.

Saint Laurent ballet flats

Saint Laurent

Nour leopard-print calf-hair flats

Leopard print will always stay classic and timeless.

Luna Slipper / Chocolate Leather

Le Monde Béryl

Luna Slipper

Chocolate brown is such a chic alt to black.

Flat Leather Pointed Toe Shoe - Women | Mango United Kingdom

MANGO

Flat Leather Pointed Toe Shoe

A very simple but effective pair.

Suede Pointed Ballet Flats

ZARA

Suede Pointed Ballet Flats

A suede pair feels very 2026.

2. Football Trainers

Capris and football trainers outfit.

Style Notes: Swap in football trainers for a bit of streetwear edge. Why not opt for a pair with a fold-over tongue to channel an off-duty It girl look?

Shop the Look:

Adidas Japan Shoes.

No one does a classic sports shoe quite like Adidas—iconic, timeless and endlessly wearable.

Women's Orbit Flash Sneaker in Sea Salt/caramel

Bottega Veneta

Orbit Flash Sneaker

This off-white colour screams quiet luxury.

Tb.490 World Club Belgium Leather Sneakers

ALOHAS

Tb.490 World Club Belgium Leather Sneakers

ALOHAS make every shoe style you can think of and make them well.

Soft Sneaker

Coloured ribbons on trainers give them a bit of character.

Gola Classics Women's Stadia '86 Trainers

Gola

Gola Classics Women's Stadia '86 Trainers

I love the colourway on this pair and the foldover tongue style.

3. Flip-Flops

Flip flops and leggings outfit.

Style Notes: On a warm day, pair flip-flops with leggings for an easy, laid-back look. Sticking to minimal, simplistic designs can also be chic.

Shop the Look:

Jessie Thong Sandal

Reformation

Jessie Thong Sandal

A pair of leather flip-flops offer more support but are low-effort and minimal.

Topanga Flip Flop Sandals

YSL

Topanga Flip Flop Sandals

A pop of colour can spice up a simple outfit.

White Lamb Leather Pointed Toe Flip Flops

Ami Paris

White Lamb Leather Pointed Toe Flip Flops

Be brave and try a different shaped flip flop.

Women's Thong Sandal With Double G

Gucci

Women's Thong Sandal With Double G

Flip flops that also give you some height? Sign me up.

Calypso Suede Sandals

GIANVITO ROSSI

Calypso Suede Sandals

Neutral-toned flip flops can offer a more refined take on an otherwise casual staple.

Shop My Favourite Leggings:

Alo yoga leggings

ALO

Softsculpt High-Waist Legging

These ALO leggings feel silky smooth on your skin.

On black leggings

ON

Studio Flared Leggings 30" Sakura

Add a bit of flare for fun.

Cotton Leggings

H&M's leggings are the best on the high street.

Stretch Spacer High-Rise Pant - Black - Xs

lululemon

Stretch Spacer High-Rise Pant

The perfect cropped pair to show off your shoes.

Cotton Jersey Foldover Pant | Soot | Xxs

SKIMS

Cotton Jersey Foldover Pant in Soot

As the name SKIMS suggests, these leggings feel like a second skin.

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I’ve Done the Research—These Are the Flat Shoes That Look Chicest With Leggings - Vanity Fair Fashion