Last Updated on January 20, 2026 by Martina McKeough
I thought I would chat about my winter shoe checklist which I created after years of heading to my shoe closet and wondering what I should be wearing when the weather suddenly got colder and wetter. Instead of thinking I have nothing to wear and impulse buying cute but impractical boots and sneakers I decided to get serious about getting my act together and making better choices.
I started to create a winter shoe capsule wardrober so that I had a small but intentional collection of shoes that covered scenarios from snowy weather to holiday parties. I wanted to create the right mix of shoes that kept my feet stylish, warm and comfortable. It was a great solution to my old problem of owning nearly 15 pairs of identical black boots for everything!
So here are the nine winter shoes I swear by and that will see you through workdays, weekend errands, travel and those “oh wow, it’s really snowing” mornings.
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Classic Leather Ankle Boots
If I could only keep one pair of winter shoes, it would be these. Classic leather ankle boots are the true multitaskers they work with jeans, trousers, skirts, and dresses, and they can go from a casual coffee date to a client meeting without missing a beat.
If you are curating a capsule wardrobe pick a pair that are smart and practical so you can wear them anywhere. I tend to stick with low heels for daytime comfort and practicality.
What to look for:
- Weather-resistant leather (bonus if they’re pre-treated for water resistance).
- A comfortable block heel or low stacked heel.
- Neutral colors like black, brown, or taupe so they go with everything.
Franco Sarto women’s Gracelyn Low Block Heel Ankle Boot
Waterproof Snow Boots
How much you spend on these really depends on how many snow days you are going to have to deal with in a year. I live in the UK so at most we get a week or two of snow in a year. That means that the snow boots I bought aren’t particularly expensive.
So why do I have a pair? Well those few days a year still mean I have to go out and walk on slippy treacherous sidewalks so I don’t want to fall over. I already have a dodgy hip so the last thing I want is to fall and break something or make it worse. Plus occasionally I go on holiday somewhere cold (Tromso Northern Lights tour) and I need snow boots.
However if you live somewhere that gets really heavy snow each year then buy the best pair you can afford.
I used to think snow boots were purely functional but these days, brands have stepped up their design game. You can absolutely find insulated, waterproof boots that keep your toes warm and look good.
Non-negotiables:
- Warm lining – look for shearling, faux fur, or thermal insulation.
- Slip-resistant soles — icy sidewalks are not the place for fashion risks.
- Waterproof construction — not just water-resistant.
Style tip: Go for a slimmer silhouette so you can wear them with leggings or skinny jeans without looking like you’re headed to the Arctic.
UGG Adirondack Boot III Women’s Boot
Chelsea Boots
For more casual wear I love Chelsea boots. They have no zips, and no laces so I can just pull them on and go. They’re perfect for mild, dry winter days when you want something sleeker than snow boots but still practical.
As it can get icy in the UK I look for boots that have good tread and traction so I can stay upright.
What to look for:
- Leather or treated suede for weather resistance.
- Chunky solved soles with good traction
Style tip: Try them with cropped trousers or midi skirts for an effortlessly chic vibe.
Sam Edelman Women’s, Lue Boot
Dressy Heeled Boots or Booties
For evenings out or events, I keep a pair of dressy heeled boots that make me feel instantly put-together.
I try and avoid really high thin heels in the winter and isntead look for block or wedge heels that give me that extra bit of stability.
What to look for:
- Again water resistant leather is an absolute must in case of rain
- Find elegant mid heeled boots that are easy to walk in when the weather isn’t great
Style tip: If you want to wear them with dresses, choose a fitted ankle that tucks neatly under hemlines.
Kate Spade New York Women’s Dakota Zip Up Heeled Bootie
Knee-High Boots
I love knee high boots because in winter they keep more of my leg warm than ankle styles. They are great if it is windy or rainy plus the style is a classic that will work for years.
The only issue I have is that sometimes the styles I want don’t come in a wide calf which is a really common issue for people. Stores have got better at offering more choices but there are still styles that I covet that won’t fit on my legs.
Style tip: Choose smooth leather in a neutral tone for a timeless look. This style of boots works beautifully with skinny jeans or leggings.
Naturalizer Women’s Rena Knee High Riding Boot
Casual Winter Sneakers
Yes, sneakers can be a winter thing as long as they’re made from leather or other water-resistant materials and you aren’t in full on snow season. I wear these for errands, weekend brunch, or casual days when the weather isn’t bad.
Don’t think about canvas styles as your feet will get wet and they will stain. Leather works great as it is breathable and allows sweat out but still keeps your feet warm and dry.
What to look for:
- Neutral tones for maximum versatility.
- A slightly thicker sole for insulation.
- Make sure you get a rubber sole to prevent slipping.
Style tip: Pair them with cozy socks that peek just above the shoe cute and practical.
Veja Women Campo Sneakers
Loafers or Flats with Lining
Sometimes winter days don’t actually require boots especially if you’re mostly indoors. That’s when lined loafers or flats come in. They’re a polished alternative for the office, and they won’t leave you sweating when you’re inside all day.
Loafers are great to wear on the way to the office especially if you have a commute on a train or subway. They are also pretty comfortable to walk in.
What to look for:
- Insulated lining or shearling interior.
- Structured shape for a professional finish.
- Lug soled loafers tend to have bettr tread and traction.
Style tip: Wear with slim trousers and a chunky knit for a smart-casual work look.
Coach Women’s Leah Platform Loafer
Cozy Shearling-Lined Shoes
These are my “weekend uniform” shoes think slipper-shoes, moccasins, or shearling clogs. Perfect for travel, errands, or lounging. They’re not heavy-duty snow shoes, but they’re heavenly for slipping on after a long day.
UGG’s and Birkenstocks do some great indoors shoes or you can have a look around for some of the copycats that are out there if you are on a budget.
Style tip: Choose a style you’re comfortable wearing outside too, that way, you can run a quick errand without changing shoes.
Birkenstock Women’s Boston Soft Footbed Sandals
Statement Party Shoes
Most of my choices so far have been quite practical but sometimes you need a pair of shoes that simply looks fabulous and party shoes are where I care less about practicality.
I don’t wear them on the way to the venue if I’m walking or on public transport instead I pop them in my bag to change into.
In winter think about buying statement party shoes in rich fabrics (velvet, satin) or sparkly finishes. These are perfect for Christmas events that tend to happen at this time of year.
Sam Edelman Women’s Hazel Pump
How to Make Your Winter Shoe Capsule Wardrobe Work
This winter shoe checklist works because you are covering every possible cold-weather scenario without overcrowding your closet. The trick is choosing versatile colors and investing in quality materials so your shoes last more than one season.
Here’s how I keep mine fresh and functional:
- Rotate pairs so you’re not wearing the same ones every day.
- Store with shoe trees or stuffing to keep their shape.
- Clean and waterproof regularly, especially after snow or rain.
- Invest in a boot dryer if you are in a snowy or wet area they are a gamechanger.
What Winter Footwear Are You Going To Buy This Season?
A well-curated winter shoe collection is like a wardrobe safety net. You’ll never stand in front of your closet wondering, “What can I actually wear in this weather?” Instead, you’ll have exactly what you need for workdays, cozy weekends, date nights, and surprise snowstorms.
The best part? You don’t need to spend a fortune or have a mountain of shoes. Just invest in the right styles, and you’ll be set with stylish, comfortably footwear that will never make you feel unprepared.
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