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 styles to avoid. As always, these are just their opinions—if you like wearing tights with the shoes they don’t, that’s totally okay! But in the interest of feeling out the best pairings, I thought this would make for some insightful learnings.
Keep reading to discover their tips for styling tights and shoes this winter..
4 Shoes Our Editors Won’t Be Wearing With Tights This Year, and 4 They Are
Passing: Trainers
Wearing: Knee-High Heeled Boots
“Personally I’d never wear trainers with tights. I always 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 sneaks, I’m actually very open minded when it comes to wearing tights with specific shoe styles—I think because I wear tights so much during winter. However my favourite thing to wear them with (especially black pairs) is a pair of black knee-high heeled boots. I’m petite in height, and while 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 KNEE-HIGH HEELED BOOTS:
H&M
Knee-High Leather Boots
Shop these whilst they’re on sale.
Mango
High Heel Leather Boot
Style these with tights or wear with bare legs.
Reformation
Nylah Nappa Knee Boot
These also come in a brown croc-print style.
Passing: Loafers
Wearing: Riding Boots
“I personally 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 pair 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 mini skirts I would usually pack away during the colder months.” Brittany Davy, Editorial Assistant
SHOP RIDING BOOTS:
& Other Stories
Leather Riding Boots
Style with a minidress or tuck these into jeans.
These also come in dark brown.
Ralph Lauren
Brooke Burnished Leather Riding Boot
These classic boots are a wardrobe hero you’ll never tire of.
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 failsafe 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, they exist in different seasonal wardrobes, and while I’m happy to wear mesh and leather pumps throughout spring and summer, tights are strictly my reserve for cold weather cosiness. Something about the “delicate-ness” of a pretty slip-on doesn’t need a grounding pair of tights, not to mention the potential for slippage” Remy Farrell, Shopping Editor
SHOP POINTED-TOE HEELS:
Zara
Patent Effect Slingback Shoes
These look much more expensive than they are.
Mango
Pointed-Toe Heeled Shoes
The burgundy colour trend is taking off this winter.
Shop these while they’re on sale.
Passing: Peep-Toe Shoes
Wearing: Mary Janes
“While I’ve seen some supremely chic outfits consisting of peep-toe shoes and elegant sheer tights, for me, it’s a combination that never feels quite right. Preferring to style my peep-toes with bare legs, these are some of the few shoes that I reserve for the warmer months.
“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 knit dresses and long skirts I love styling all season long.” Poppy Nash, Managing Editor
SHOP MARY JANES:
& Other Stories
Mary-Jane Leather Pumps
These chocolate brown shoes are a chic alternative to black for the winter months.
Mango
Patent Leather-Effect Ballet Flats
I don’t think these will stay in stock for long.
Sézane
Georgia High Mary Janes
These also come in three other shades.