I don't know about you, but I always find that my wardrobe feels a little small at the start of the winter season.
It’s not that I don’t have great pieces to choose from, it’s just that after months of wearing lighter layers, I’ve fallen out of sync with styling my heavier cold-weather staples. Determined to expand my daily outfit possibilities, I’ve come to realise that tights are the ultimate key to unlocking more of my wardrobe during winter. With the right pair, I can extend the life of my favourite dresses, skirts and even shorts from the warmer months, giving my looks a much-needed refresh.
To make this my chicest winter yet, I turned to a few of my stylish colleagues for their expert advice on the best shoe pairings to wear with tights this season—and the combos to avoid. As always, these are just their opinions—if you like wearing tights with the shoes they don't, that's totally okay!
Keep reading to discover our tips for styling tights and shoes this winter.
4 Shoes Our Editors Aren't Wearing With Tights This Year and 4 They Are
Passing: Trainers
Wearing: Heeled, Knee-High Boots
"Personally, I'd never wear trainers with tights. I think they look cool on other people, so it's not to say this is a hard fashion "rule", but if not done with a certain flair, it can just look scruffy, and I'd prefer not to risk it—especially if it's a white-trainers-and-black-tights situation.
"Aside from sneakers, I'm actually very open-minded when it comes to wearing tights with specific shoe styles, probably because I wear them so much during winter. However, my favourite thing to wear my tights with (especially the black pairs) is a pair of black, heeled, knee-high boots. I'm petite in height, and whilst this is no bad thing, I love how this combination makes my legs and overall silhouette look when I'm wearing short dresses and skirts." – Maxine Eggenberger, deputy editor
SHOP HEELED, KNEE-HIGH BOOTS:
Shop these whilst they're on sale.
A classic pair you'll always come back to.
These also come in a brown croc-print colourway.
Passing: Loafers
Wearing: Riding Boots
"I wouldn't wear loafers with tights. Firstly, they remind me too much of my school days, but I also find that wearing tights can be uncomfortable because the material is too thin to protect my ankles from the stiffer leather of the shoes. For this reason, I’m far more likely to wear my loafers with chunky socks.
"I will, however, be wearing tights with my riding boots this winter. Not only does this combo look extremely sophisticated, but it also allows me to get much more wear out of the shorts and miniskirts I would usually pack away during the colder months." – Brittany Davy, editorial assistant
SHOP RIDING BOOTS:
Style with a minidress or tuck in your jeans.
These also come in dark brown.
A Ralph Lauren classic.
Passing: Ballet Flats
Wearing: Pointed-Toe Heels
"There is something extremely chic about the sleek silhouette that a pair of tights and pointed-toe shoes creates. Going together like a white tee and jeans, whenever I want to feel dressed up in winter, I always come back to the fail-safe option of sheer or opaque tights with a pointed-toe heel and a miniskirt or dress.
"I can't say that the idea of tights and ballet flats has ever really crossed my mind. For me, the two exist in different seasonal wardrobes, and whilst I'm happy to wear mesh and leather pumps throughout spring and summer, tights are strictly for cold-weather cosiness. A pretty, delicate slip-on ballet flat doesn't need a grounding pair of tights, not to mention the potential for slippage." – Remy Farrell, shopping editor
SHOP POINTED-TOE HEELS:
These look much more expensive than they are.
The burgundy colour trend is taking off this winter.
Shop these while they're on sale.
Passing: Peep-Toe Shoes
Wearing: Mary Janes
"Whilst I've seen some supremely chic outfits consisting of peep-toe shoes and sheer tights, for me, it's a combination that never feels quite right. I prefer to style my peep-toes with bare legs, so these are some of the few shoes I reserve for the warmer months.
"On the other hand, Mary Janes and cosy tights are my go-to winter pairing. Sturdy enough to tackle puddle-strewn streets, these timeless shoes still feel light and pretty. They’re the perfect match for the knitted dresses and long skirts I love wearing all season long." – Poppy Nash, managing editor
SHOP MARY JANES:
These chocolate-brown shoes are a chic alternative to black for the winter months.
I can see these on the feet of very stylish French women.
These also come in three other shades.
-
Katie Holmes Just Wore the Cheap Styling Trick That Instantly Adds Outfit ValueLow cost, high look.
-
I Never Thought I'd Wear This Weird Sneaker Trend, But I Can't Stop Getting Compliments On ItThey're kooky in the best, most Miu Miu way
-
In 2026, Fashion People in Paris and NYC Will Still Be Wearing This High-Net-Worth Shoe TrendTimeless.
-
Suddenly, All the Chicest People I Know Are Upgrading Their Outfits With This Winter Accessory TrendInspired by the early 1900s.
-
I Just Got Back From the Swiss Alps—4 Chic Trends I Saw EverywhereAprès-ski chic.
-
The Pretty Shoe Trend Celebs Can't Stop Wearing on the Red Carpet in 2025It's no coincidence.
-
Elsa Hosk's Already Wearing 2025's First Viral Sneaker TrendFor $80? Say less.
-
Fashion in Aspen Should Be Studied—5 Trends Chic People Are Wearing and Leaving BehindYou heard it here first.
