Try as I might, every morning I go to my wardrobe with the intention of styling jeans or trousers, but every morning I step away in a comfortable pair of leggings. Honestly, I can’t seem to rip myself away from them—but, really, why would I want to? With a comfortable finish and sleek silhouette, they encapsulate the exact style energy I’m trying to hone right now.
Naturally, when I’m wearing my leggings at home, I’m styling them with fluffy socks and slippers. But, when I do leave the house, I want to retain the comfortable finish while amping up the elegance. Inspired by the surprisingly chic leggings and flat shoe outfits I’ve seen in recent weeks, I’ve curated an edit of the chicest ways to style leggings and flats this season. Read on for inspiration.
DISCOVER THE CHICEST FLAT SHOES TO WEAR WITH LEGGINGS THIS SEASON
1. LEGGINGS + MARY JANES
Style Notes: An unexpected but highly elegant combination, leggings and mary janes are a chic two-piece outfit I’ll keep coming back to. If I want a cosier finish I’ll style this with socks, but if the sun is shining I’ll often go without.
SHOP LEGGINGS AND MARY JANES:
Mango
Mid-Rise Skinny Leggings
A simple pair of leggings is, in my opinion, a wardrobe non-negotiable.
& Other Stories
Square-Toe Ballet Flats
Style these with crisp white socks or wear without.
These also come in light and dark grey shades.
Marks & Spencer
Unlined Leather Mary Jane Ballet Pump
This also comes in three other shades.
2. LEGGINGS + KNEE-HIGH BOOTS
Style Notes: A classic leggings and tall boots combination is one of the chicest ways to style leggings, in my opinion. To add to the elegance, style with a wool coat or blazer, otherwise pair with an oversized knit for a low-key look.
SHOP LEGGINGS AND KNEE HIGH BOOTS:
Style these with an oversized knit or dress it up with a smart wool coat or blazer.
Simple riding boots are a wardrobe staple you’ll never tire of.
The Row
Essentials Woolworth Stretch-Ponte Leggings
I always come back to The Row for their elevated basics.
Zara
Buckle Knee-High Boots
These look much more expensive than they are.
3. LEGGINGS + LOAFERS
Style Notes: Over the past few seasons, simple leather loafers have become an absolute pillar of my wardrobe. Enough to smarten up the most casual look, leggings and loafers are an unexpected combination I’ll keep reaching for throughout the coldest season.
SHOP LEGGINGS AND LOAFERS:
Reformation
Ecostretch High Rise Legging
Shop these whilst they’re on sale.
Massimo Dutti
Penny Loafers
Loafers have become a pillar of my winter wardrobe.
Toteme
Jacquard-Knit Leggings
Style with sleek leggings or dress these up with a pointed-toe heel.
Marks & Spencer
Leather Loafers
In my opinion, Marks & Spencer’s basics are some of the best out there.
4. LEGGINGS + TRAINERS
Style Notes: Leggings and trainers are a classic for a reason. Ideal for zipping around during a day of errands, this classic combination will keep you comfortable for hours. For a modern silhouette pair with tall white socks and accessories with a pair of shades.
SHOP LEGGINGS AND TRAINERS:
Arket
Seamless High Waist Tights
Honestly, these look more expensive than they are.
Salomon’s trainers are a fashion person’s favourites.
Whistles
Black Super Stretch Trouser
These come in both petite and regular lengths.
Adidas
Taekwondo Striped Leather Sneakers
These are set to be a major trainer trend next season.
