A few days ago, we talked about the essential coats to have in your winter outerwear wardrobe, and today it’s all about the footwear. From keeping your feet warm and dry to adding the perfect finishing touch to your outfit, having the right shoes and boots can make all the difference.
Winter weather varies, of course, depending on where you live. Here in Philly, it can be cold from September to May, so I spend a lot of time in winter shoes. From leather sneakers to snow boots, these are the styles I swear by to get me through every kind of winter weather.
Women’s Winter Shoe Must-Haves
For size reference, I usually wear an 8 in closed-toe shoes, and I sometimes size up to an 8.5. I’m almost always a 39 in European sizes.
Everyday Ankle Boots: Versatile Favorites for Casual Days
similar Blondo boots (8) // Bernardo coat (M) // old jeans & sweater
Ankle boots are probably the most versatile style of winter shoe because they’re practical, they go with everything, and they can be dressy or casual. Since winter weather can be messy, most of my ankle boots are a glossy leather or waterproof suede.
Blondo offers a variety of stylish and functional fashion boots that hold up well to inclement winter weather. They’re also comfortable to walk in, making them great for travel. The waterproof suede boots I’m wearing here are an older style, but the Blondo Alida Waterproof Bootie is similar. I like the block heel for walkability, and the textured rubber sole provides good traction.
similar Blondo boots (8)
When I want to splurge, Aquatalia does a high quality waterproof boot made in Italy with premium materials. I often purchase this brand during the Nordstrom Anniversary Sale, or late in the season when I can find a good deal, but evidently they were bought out by another shoe brand earlier this year, and I’m not seeing many around this season. I hope they bring them back!
similar boots (but not waterproof) // Naadam boatneck sweater (S) // Andrew Marc coat (6) // MOTHER jeans (29) – on sale // similar bag
To keep your footwear current, look for Chelsea boots, square toe styles, and taller shafts that slip easily under more relaxed the denim styles that are trending. My favorite everyday boots so far this season have already mostly sold out, unfortunately. They are the black rag & bone Walker Chelsea Boot and the brown Veronica Beard Lada Chelsea Boot, both from the #NSale, but I rounded up more options for you below.
More everyday boot recommendations:
Pointy Toe Ankle Boots: Sleek Styles for a Polished Look
Vince Boiled Cashmere Cardigan (M) // KUT from the Kloth Ana Coated Flare Jeans (6) // Marc Fisher Kolton Kitten Heel Bootie (8) // triple chain necklace
When I want to level up my look, but I still want the warmth and practicality of a boot, I love a sleek pointy toe ankle boot. Kitten and stiletto heels are having a moment right now, and I love the chic elegance these styles add to my favorite denim outfits.
I recently added these Marc Fisher Kolton Kitten Heel Booties to my closet, and I know I’ll get a lot of wear out of them. They have a dressy vibe, but the chunky kitten heel still offers some stability and it’s low enough to be easily walkable.
Marc Fisher Kolton Kitten Heel Bootie (8)
But if you need something a little more practical, a block heel with a pointy toe is a nice compromise. It levels up the look but still gives you plenty of stability.
similar Marc Fisher boots (8) // Vince sweater (S) // FRAME denim (29) // Quince box bag
More pointy toe boot recommendations:
Snow Boots: Weatherproof Options for Wet and Wintry Weather
similar The North Face parka (M) (longer option) // similar turtleneck (M) // MOTHER denim (29) (more sizes) // UGG boots (8.5)
You can’t talk about winter shoe essentials without talking about snow boots! I’ve had a lot of snow boots over the years, and most of my favorites have been Sorel, but the UGG Adirondack tops them all.
I first discovered these boots many moons ago when I was visiting my parents in Maine, and I borrowed my mom’s. I even wrote a post about it.
We just won’t talk about the jeans with the busted out knees in sub-freezing Maine winter temperatures… It was 2017, after all! (And oh, how I loved those jeans! I actually have a tag for that in my archives because I wore them so much! But I digress.)
I didn’t buy myself a pair of the UGG Adirondacks at the time because I had other snow boots, but a few years when I was looking for a new pair, I did some internet research that pretty much confirmed that these are the best snow boots for my needs.
UGG Adirondack (8.5)
For starters, they’re shockingly lightweight and flexible, considering how bulky they appear. Plus, they’re completely waterproof and fully lined with UGGpure™ – a textile made from wool that’s designed to feel and wear like genuine shearling. They’re so cozy and soft inside that I never wear socks with mine.
You can also flip up the top of the shaft and lace them all the way up to make them taller and warmer, but I usually wear mine turned down as pictured above.
Not only do I wear these with jeans when we get snow, I keep them in the mudroom and pull them on to go to and from the gym. They’re super warm and cozy, and I often have to cross wet or snowy grass, so they keep my sneakers from getting muddy, and my feet stay warm and dry.
More snow boot recommendations:
Leather Sneakers: Casual and Comfortable for Milder Winter Days
VEJA Esplar (8) // J.Crew cashmere trouser socks
Speaking of sneakers… sometimes I don’t want to wear boots in the wintertime. When I want a casual, sporty look that isn’t a boot, I usually wear a leather or suede sneaker. I’ve been wearing the VEJA Esplar for years, as they’re super versatile and hold up well to wear and tear.
The Vince Oasis is one of the newer additions to my sneaker wardrobe, which is becoming massive! They’re nice for winter because not only does the leather protect my feet from the elements, they have a gum sole that provides good traction on slippery pavement. Plus, they have that great casual-cool vibe that I love. Obviously, I would not wear these in the snow, but we don’t get a lot of that here in eastern Pennsylvania.
Vince Oasis (8)
I also have the suede version in burgundy, which I love, and I also have the adidas Spezial in a versatile shade of brown. Non-white sneakers are trending this fall, and I’m enjoying the lower contrast look when I’m wearing darker colors, as opposed to the stark contrast of a white sneaker.
Of course, suede sneakers should be treated with a good suede protector, and I won’t wear them on really messy days, but they’re a nice option to have if you wear a lot of sneakers.
Vince Oasis in Malbec (8) // quilted vest (S) // MOTHER Dazzler (29) // camel hoodie (S) // Madewell bucket bag
Of course, there are plenty of other options for leather sneakers; these are just my current favorites. If you want to update your sneakers for the season, non-white sneakers are trending, as well as metallics. And sneaker boots are another option if you want that same cool-casual vibe with more warmth and protection from the elements. Also, a platform will keep your feet a little further off the cold ground… every little bit helps!
More winter sneaker recommendations:
Tall Boots: Timeless Silhouettes for Elevated Winter Style
Dolce Vita Raj Knee High Boots (8) // Frank & Eileen Izzie Party Dress c/o (M) // Spanx tights (M)
After being on the back burner for a while, tall boots are back this season. We’re mostly seeing them with dresses and skirts, rather than over skinny jeans, although if you like that look, it can be styled in a modern way.
Western styles are trending, and I picked up these Dolce Vita Raj Knee High Boots when I was shopping at Evereve recently. They’re very comfortable, and I love how they fit my smaller calves.
Dolce Vita Raj Knee High Boots (8)
They also look great under longer skirts; here’s how I wore them with a denim midi skirt and cozy turtleneck.
Vince turtleneck (S) (budget option) // denim midi pencil skirt (29) // Dolce Vita boots (8) // belt (M) // earrings // bracelet
Kitten heels and sleek stilettos are also having a moment, but I don’t really need anything that dressy. If you want a more timeless look, go for a sleek almond toe and avoid the slouchy styles.
More tall boot recommendations:
Winter Flats: Chic Alternatives to Boots
While I don’t wear my loafers and ballet flats a lot in the dead of winter, we do get mild days here and there, so I keep a few pairs in my closet all year ’round.
Sam Edelman Loraine Loafer (8) // old AGOLDE jeans // old Evereve sweater
The Sam Edelman Loraine Loafer is very comfortable and a good value for the price point. It’s inspired, of course, by the iconic Gucci loafer, which is also amazing if it’s in your budget.
Montecito Sweater (S) c/o // Eileen Relaxed Button-Up Shirt (S) c/o // Derry Illusion Pull-On Jean (29) c/o // similar loafers
When I want something with a more trend-driven, edgy vibe, I love my Franco Sarto Emma Pointed Toe Slingback Flats, but I don’t wear them on the coldest days because of the open heel. If you live in an area with milder winters, these are a great price point, and they’re comfortable to..
Franco Sarto Emma Pointed Toe Slingback Flats (8)
Franco Sarto Emma Pointed Toe Slingback Flats (8) // red blouse (S) // AG Mari jeans (29)
Shop more flats for winter:
Pumps: Elegant Essentials for Dressier Occasions
Marc Fisher Zala Block Heel Pumps (8) // Andrew Marc Bouclé Wool Coat (S) // Vince Crop Leggings (M) // similar CeCe blouse (S)
The Marc Fisher Zala Block Heel Pumps have been my go-to pumps for wintertime for several years now. When I want to dress up my jeans, or I need a dress shoe that isn’t a bootie with a dress or business casual outfit, these are my favorites. The block heel is walkable, while the pointy toe is flattering, and the chunkier vibe works well for wintertime.
Marc Fisher Zala Block Heel Pumps (8)
That said, I just added these Sam Edelman Vienna Pointed Toe Pumps to my closet, so I have a more classic pair. I used to have the Sam Edelman Hazel in several colors, but the Vienna has a lower heel, which is kinder to my finicky feet. Plus, it’s more on-trend at the moment.
The nice thing about traditional pumps is, you can easily wear them with tights or hose for added warmth, but weather permitting, slingback pumps are trending, and I think they’re so chic and stylish. This leopard hair calf pair is gorgeous, and they can be dressed up or down.
Sam Edelman Bianka Slingbacks in Granada Tan (8.5)
These outfits are both from the fall, but it gives you an idea how versatile these are.
Sam Edelman Bianka Slingbacks in Granada Tan (8.5) // MOTHER Weekend in Teaming Up (39) // brown cowl neck top (S) // green sweater dress (L)
And I recently picked up the mesh style with the black dots, which are perfect for holiday looks.
Sam Edelman Bianka Slingback Mesh Pointed Toe Pump (8.5) // Sanctuary Sequin Perfect T-Shirt (S) // AG Mari Slim Straight Ankle Jeans (29) // J.Crew bracelet // Ettika earrings
More winter pumps:
What are your essentials shoes for winter?
As with most wardrobe items, everyone’s list of essentials will look a bit different. I’d love to hear from you! Which shoes do you consider essential for winter, and are there any you would add to this list?
