Essential Shoes To Have In Your Winter Wardrobe

I briefly touched on shoes in my Winter Wardrobe Essentials post last month, but today I’m doing more of a deep dive into the essential shoes to have in your winter wardrobe.

Winter weather varies, of course, depending on where you live, but I’m writing this post from the perspective of someone who has spent the majority of her life in the Northeast. Here in Philly, it can be cold from September to May, so I spend a lot of time in winter shoes. From sneakers to the boots, these are the shoes I like to have in my closet for every type of winter weather.

Winter Shoe Essentials for Women

Best Waterproof Dress Boots: Blondo (save) or Aquatalia (splurge)

Blondo at Nordstrom // Aquatalia at Nordstrom

When I want to dress up but it’s snowy or wet outside, I rely on Blondo and Aquatalia for waterproof suede fashion boots that are both practical and stylish. They’re also very comfortable to walk in, so both brands are great for travel.

Bernardo Hooded Puffer – on sale (M) // Sanctuary stripe sweater (S) // PAIGE denim (29) // Blondo Sadie (8)

Blondo is more of a mid-range price point, and Aquatalia is higher end, but both offer a variety of stylish and functional fashion boots that hold up well to inclement winter weather.

These are the Blondo Sadie, and I love how they have a memory foam footbed and a chunky heel for ultimate comfort, but they look good too.

Blondo Sadie (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.

similar Aquatalia booties // Andrew Marc coat (6) // jeans (29) // similar bag

They’re truly gorgeous boots, and they hold up well over the years. Their styles are a little more fashion-forward than Blondo, but you can also find nice options at the lower price points. Others brands that do good waterproof fashion boots are Cole Haan, Dolce Vita, Naturalizer, and La Canadienne.

Best Lug Sole Boots: Steve Madden (save) or Paul Green (splurge)

Steve Madden Leopold // Paul Green Selma

Lug sole boots are great for winter because they provide good traction on slippery surfaces, and they have a bit of a platform that keeps  your feet up off of the ground, which ultimately keeps them warmer than a flatter sole.

Steve Madden Leopold (8)

The Steve Madden Leopold is a nice, affordable pair of fashionable lug sole boots for wearing with a variety of denim styles. They aren’t weather-proof, per se, but they’re made of a hard leather that holds up to messy conditions.

Here’s how I wore them with black straight leg jeans, a cozy sweater, and a practical insulated rain coat. I love this cheerful Hickory color!

Helly Hensen Lisburn (M) // Treasure & Bond sweater (S) // AG Jeans (29) // Steve Madden Chelsea Boots (8) // Madewell bucket bag // necklace

For a splurge, I discovered Paul Green lug sole boots at the #NSale last summer, and they are truly luxurious. This pair is on sale at Nordstrom Rack and fully stocked!

Paul Green Selma Lug Sole Bootie (8)

These boots are so comfortable to walk in, and I love the styling with the roller buckle, chunky lug sole and stacked block heel.

I styled those here with flare leg jeans, a cozy fisherman knit sweater, and a bold green quilted vest.

J.Crew vest – 30% off (S) // Jenni Kayne sweater (S) (similar for less) // MOTHER denim (29) // Paul Green Selma Lug Sole Bootie (8)

There are so many other great options for lug sole boots; these are just the ones I currently have in my closet.

Best Winter Fashion Boots: Sorel

Sorel at Nordstrom // Sorel at Zappos

When it comes to stylish snow boots, it’s hard to beat Sorel. They’re the perfect marriage of form and function, and they have so many styles to choose from. There’s pretty much something for everyone.

Sorel Hi Line Chelsea Boots (8)

I personally love this Chelsea boot style with the rugged lug sole and large block heel. The color combination is so pretty, although this exact color way is from last season, and I don’t think they carry it anymore. There are a couple sizes left at Nordstrom.

These boots run true to size, or size down if in between. They’re also especially good for narrow feet. I have the size 8, for reference.

Another good option in this category is the Sorel Brex Chelsea Boot, which is on sale at Zappos and Nordstrom.

boots (8) // jeans (28) // sweater (S; similar for less)

These also run true to size and are very comfortable and practical. I just decided that the Hi Line Chelsea Boots are more my style.

Best Knee Boots: Sam Edelman

 at Nordstrom // at Bloomingdale’s

Sam Edelman Shale (8)

I’m a longtime fan of Sam Edelman for knee-high boots. He does such good designs, and the quality is there without totally breaking the bank.

I don’t wear knee boots a lot right now, but I do love this pair that I picked up during the #NSale last summer. The suede makes them a bit tricky for messy winter weather, and I also have the Sylvia but I haven’t had a chance to wear them yet.

Both are low inventory, but you can peruse Nordstrom and Bloomingdale’s for more options.

Best Snow Boots: UGG Adirondack

at Zappos // at Nordstrom // at Bloomingdale’s

UGG Adirondack

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 9 years ago when I was visiting my parents in Maine, and I borrowed my mom’s. I even wrote a post about it back then.

essential shoes to have in your winter wardrobe: snow boots

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 last year 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.

The North Face Metropolis Down Coat (M) (also at Nordstrom and Zappos) // cashmere turtleneck (S) // MOTHER denim (29) // UGG Adirondack (8)

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 protect my sneakers from getting muddy and keep my feet warm and dry.

Best Leather Sneakers for Winter: VEJA Esplar or Vince Oasis

VEJA at Bloomies (39) // VEJA at Nordstrom // Vince Oasis at Bloomies (8) // Vince Oasis at Nordstrom (8)

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 my VEJAs, or my new Vince Oasis low top lace-up sneakers.

VEJA Esplar (8) // J.Crew cashmere trouser socks // AGOLDE Riley Long Jean (29)

I’ve been wearing these VEJA Esplars for years, and I have a couple different color combos. They are a bit stiff at first, but they break in quickly, and they are super versatile and hold up well to wear and tear.

VEJA Esplar (39) // Lucky Brand plaid jacket (S) // Madewell top (M) // AGOLDE Riley Long Jean (29)

The Vince Oasis is the newest addition 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 here in Philly, we don’t get a lot of that.

Vince Oasis (8)

I’m not wearing socks here, but sometimes I do wear my J.Crew cashmere trouser socks with these sneakers when I want extra warmth. If I want the sockless look, I wear my Sheec Active mid-cut no-show no-slip socks.

Rails wool blend jacket (S) // Nordstrom cashmere crew (S) // PAIGE Gemma slim jeans (29) (some sizes on sale) // Vince Oasis (8) // similar bag

Of course, there are plenty of other options for leather sneakers; these are just my current favorites. And sneaker boots are another option if you want that same cool-casual vibe with more warmth and protection from the elements. Sorel has a lot of good options for that.

Best Winter Flats: Sam Edelman Loafer

at Zappos // at Nordstrom // at Bloomies

Sam Edelman Lior Loafer – sold out; Loraine is similar (8)

Another pair of essential shoes to have in your winter wardrobe is a flat loafer or ballet flat. 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) // AGOLDE Riley Long Jean (29) // 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.

Marc Fisher ballet flats (8) // AG Mari slim jeans (29) // Rails sweater (S)

I also have a couple pairs of suede ballet flats, but I really don’t wear them much this time of year.

Best Winter Pumps: Marc Fisher Varla Pumps

at Nordstrom (8)

Finally, these are my go-to pumps for wintertime. 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. I also have the Light Natural.

The sleek almond-shaped toe elevates the look, but the chunky 3″  heel keeps them walkable. They go with just about every style of pants or jeans, as well as dresses and skirts. They’re also true to size; I wear the 8.

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?

Stay In Touch

If you liked this post, be sure you’re signed up for my email newsletter. In addition to my most recent blog posts, you’ll receive exclusive newsletter content like special sales, my newest favorite finds, and an occasional peek behind the scenes — all delivered right to your inbox.

I would also love for you to join my JLS Fashion Insiders Facebook Group! This is a friendly place to discuss all matters of fashion and style with other women, share your outfits, get advice, and stay up to date on all the happenings in our community.

This post contains affiliate links. When you shop through my links, it helps support my business (at no additional cost to you) so thank you!

Join The Conversation

0 Responses

  1. I’m a California girl- no snow- but lately rain! I love my Hunter rain boots- I have a tall and short pair and I recently ordered the Sam Edelman Laguna boot in black and wore for first time yesterday in rain! Very solid and comfy!

  2. I love the way suede looks, but snowy Minnesota winters play havoc with them. They require too much TLC. 🙁

  3. Great post! I bought the Sam Edelman knee high boots when you first styled them and absolutely love them! They are so comfortable and fun to wear with dresses! If they had them in my size in black I would be tempted to get that color also!

    Do you do anything to treat these boots with a suede spray or other?

  4. I like to read comments from other readers, it enlightens me to what else is in the shoe world. I also learn a lot from the ladies on the JLS Fashion Insider FB page. That said, I live in winter conditions for almost 6 months a year so I wear Ugg Adirondacks, Stio’s Colter boots, and Ugg mini platform boots if I am dressing things up 😂. I am pretty simple ☺️

  5. I love my Aquatalia boots which I bought in the Nordstrom Anniversary Sale. I have since bought a second pair for my snowy, wet climate. Definitely a splurge, but it’s an investment piece. I have a question about sneakers. I have a pair of the P448 which I bought after seeing them on you. I tied them as you showed with the loops at the sides. Is this no longer in style? Thank you!

  6. I’ve been having mild weather this year in the NW, so I’d add my chunky Penny loafers to this list. I purchased the Banana Republic Factory, black ones and love them. They are not too chunky and comfortable. I wear the Sheec mid cut no show socks in them and have been plenty warm. I also have my new Sorel boots for wet and cold, that I purchased at Nordstrom. I also have worn my clogs some days when milder. I think we both have similar weather but you may get colder. I’m looking forward to at least one snow fall this season, but don’t know if its going to happen. Its suppose to get colder coming up and possible snow down to 1500 ft. so will see. I live at 500 ft. and if they say 1000 ft. I usually get it. I LOVE snow.
    I love Pottery Barn pillows. I purchased their round, knitted, cozy pillow, two years ago and use in the Winter. I tried to order the snowflake one this year that I missed buying last year, but it was out of stock early. I just purchased the large heart shaped sherpa look pillow from Target for my foyer bench for Valentines season. Its well made and only $20. It would be wayyyyyy more at Pottery Barn. It is too big for a couch or chair, but fun for floor decor or like I said a bench. It comes in red and ivory. I purchased the ivory.

  7. Based on what I reach for the most, my lined mules are my winter essentials footwear. I wear thick socks with them, so my feet stay nice and toasty.

  8. I live in the South so we have bi-polar weather. One morning it may be 32 and by 2:00 pm up to 63 or 64 and by dark cooling down again. You have to dress in layers alot. For boots I spray my suede ones because Mississippi is prone to damp cold and it can get wet here alot in the winter. I always have a heel on because I am petite and the only time I have tennis shoes on is at the gym. I wear Vionic & Baretraps Posture Plus some because of arch support and I have a foot insole pad also for boots with out that feature. Instructions from foot doctor for a toe problem. I loved all your boots & shoes. I wear knee high boots with dresses like you. I wear a size 5 so I can’t be too picky sometimes & mostly have to order online nowadays. Our winters start going away by March & by April we are in sandals & flip flops. Thanks for all the pics and info on the boots and what style to wear with what jean, dress pant or dress. I enjoyed learning all your tricks and tips. Happy New Year!

  9. Great post! I love the UGG Adirondacks too. I’m wondering what you think about the sizing. I went up a half-size but now wonder if I should have. It rarely snows here on the coast, so I get more use out of my Blundstones which work equally well for hiking and casual urban wear. They’re almost a year-round boot in this climate.

Leave a Reply

Your email address will not be published. Required fields are marked *

Close this search box.