Wear Your Leggings With These Precise Jackets and Shoes to Make Them Look Chic This Autumn

Irrespective of your personal views on the matter, leggings have become a true wardrobe staple. This season, the most notable autumn legging outfits do even more legwork to elevate their stature beyond something you’d aimlessly slip on to run errands. In fact, when you look at some of the most aspirational ways tastemakers style leggings, you'd be remiss to call them basic. Premium, refined and polished are other turns of phrase that come to mind as the silhouette trades the Pilates studio for the streets of Paris.

Indeed, trainers have surprisingly become the least common shoe pairing when it comes to styling them through the cooler months. As have the fleecy zip-ups and oversized knitwear they’re commonly teamed with. In their place, sleek boots and slick leather jackets have emerged, offering a more intentional take on the trend that proves their longevity as a true fashion fundamental. You could even say that the chicest autumn leggings outfits prove their full potential.

Since being co–opted by the activewear set, whether you interpret this as the neon-coloured iteration endorsed by Jane Fonda or the millennial beige colouring pioneered by Kim Kardashian, leggings have unjustly been relegated to sports drawers. For far too long, leggings have remained hidden under oversized hoodies or been tossed aside as something exclusively reserved for exercise. Now, they’re being duly considered as the effortless essential they’ve always longed to be.

These days, you’ll see stirrup leggings, a favourite of the likes of Phoebe Philo and Toteme, nestled between a scoop-neck jumper and a pair of heeled ballet flats. Or a pair of capri leggings, which have made several runway appearances at Tory Burch and Sandy Liang, layered with oversized blazers or cotton-poplin shirting. Of course, given their functional provenance, there are still covetable autumn outfits that err more on the casual side, à la Miu Miu’s autumn/winter 2023 show. Think elegant stretch-jersey styles coupled with sumptuous coats and oversized sunglasses. So, with well-founded evidence of leggings' relevance, scroll through to see the autumn outfits that make them look best.

5 Chic Leggings Outfits to Replicate for Autumn 2026

1. Grey Blazer + Stirrup Leggings + Ballet Flats

Style Notes: After strolling down Tibi’s spring/summer 2025 runway, stirrup leggings began to pique the interest of the most discerning aesthetes: expensive-looking Upper East Siders, trendy locals in London’s West End and sophisticated Parisians strolling through the Le Marais. Featuring a strap that wraps under the foot, they allow for more experimental shoe pairings whilst still feeling versatile enough to style with cult pieces like windbreaker jackets and boxy blazers.

Shop the Look:

2. Black Blazer + Capri Leggings + Heeled Mules

Style Notes: Capri leggings have been synonymous with well-heeled European women ever since Brigitte Bardot slipped into them when filming Jean-Luc Godard’s seminal French New Wave classic Contempt. Inherently stylish women across the continent are translating them for more autumnal settings by incorporating them into tailored ensembles. The result? Something that’s part Carolyn Bessette-Kennedy after-hours and Hailey Bieber in her businesswoman era.

Shop the Look:

3. Trench Coat + Brown Leggings + Riding Boots

Style Notes: Forget frazzled English women. This season, the defining dressing is what we’re coining Balmoralcore: long walks through pastoral countryside in waxy Barbour jackets surrounded by legions of corgis, several gallons of tea and a pair of Hunter wellies that would be found in the mud room of a castle in the Scottish Highlands. As the temperature drops, there’s nothing more enticing than hiding under a big trench coat, donning a pair of riding boots and tying it all up with a scarf, Sloane Ranger style.

Shop the Look:

4. V-Neck Jumper + Capri Leggings + Ballet Flats

Style Notes: Ease and comfort are two prevailing modes for getting dressed amid freezing mornings and grey skies, especially for more casual outings, but that doesn’t mean you have to succumb to wearing baggy tracksuits and stained hoodies to fit this bill. Surprisingly, a pair of leggings can do a lot to make you feel put-together. Blame this on the fact that their sculpting appearance leans toward a more considered look, but when paired with premium basics like a cashmere V-neck jumper and pointed flats, you’ll instantly feel like the best-dressed person in your local shop.

Shop the Look:

5. Textured Jackets + Black Leggings + Flat Boots

Style Notes: Arguably the most opulent leggings look on this list, the combination of the textured coat, knitted bucket hat—which just so happens to be a fixture in the wardrobes of Jennifer Lawrence, Kendall Jenner and Zoë Kravitz—and flat, knee-length boots makes it apparent that only wearing leggings when working out is underestimating their value. This outfit formula not only looks incredibly expensive, but has a slightly ‘90s rom com undertone. Who knows; wearing this on a trip to a certain Notting Hill bookstore might have you meeting your own floppy-haired Prince Charming.

Shop the Look: