Fall/Winter Fashion

Essential Shoes To Have In Your Winter Wardrobe

I briefly touched on shoes in my Winter Wardrobe Essentials, but I want to do more of a deep dive into the essential shoes to have in your winter wardrobe.

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.

Before we get started, here are some of my other winter and shoe-related posts that you may find helpful:

Winter Shoe Essentials for Women

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

Blondo at Nordstrom // Aquatalia at Nordstrom

winter shoe essentials: waterproof dress bootssimilar Aquatalia booties // similar coat (6) // jeans (29) // scarf (option)

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.

Unfortunately, my current favorites are sold out or have low inventory, so I linked to general categories above.

boots (8.5) // jeans (28)

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.

Best Lug Sole Boots Under $100: Blondo Dagger (or Dahlia)

at DSW // on sale at Nordstrom // at Bloomingdale’s

The Best Lug Sole Boots Under $100 Blondo Dagger (similar on sale at Nordstrom)

This is a great pair of fashionable lug sole boots for wearing with a variety of denim styles. I like that they have a bit of a heel, and the buckle is a fun detail. Since the shaft is narrow, you can wear them with skinny jeans or slip them under straight or bootcut silhouettes.

They’re also very warm and comfortable. I walked all over the North Shore of Boston in these one day last fall, and my feet were very happy. They run true to size; I have the 8.

Best Winter Fashion Boots: Sorel Hi Line Chelsea Boots

on sale at Zappos // on sale at Nordstrom // on sale at Macy’s

boots (8) // jeans (29)

These are a new addition to my winter shoe wardrobe this year, and I love them for a fashionable and fun winter boot that can also hold up to the elements.

As you can see, I went with the Chalk/Ceramic, which is going to be more prone to marks and stains than the black and brown leather options, but it’s fun for a change and goes great with light wash denim.

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 also on sale at Zappos, Nordstrom, and Macy’s.

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

I shared more about these in my last Try-On Haul, but they 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 Western Style Boots: Dolce Vita Volli

at Nordstrom // at Zappos // at Bloomies

Winter Shoe Essentials: Western Inspired Booties

Western-style boots are trending big time, so I wanted to include this pair because I wear mine a lot, even though I would consider this more of a fall boot.

I like these so much, I have them in all three colors (Well, my black pair is the Vikram, but it’s the same style with a higher shaft.)

boots (8) // sweater (S) // jeans (29)

These boots are extremely comfortable, and a great way to update your look without breaking the bank because they look great with all denim styles. They run true to size, or size down if in between; I wear the size 8.

Best Knee Boots: Talbots Lilia Suede Wedge Boot

at Talbots

Winter Shoe Essentials: Knee Boots

I haven’t found myself reaching for my knee boots much this winter because I haven’t been wearing skinny jeans, but I do like them with tights and dresses.

This pair from Talbots is supremely comfortable, and they’re very good quality.

Knee boots with sweater dress for winterboots (8) // dress (S) // tights (B) // earrings

They aren’t as dressy as some, so they won’t work with all styles of dresses and skirts, but they look especially nice with sweater dresses, which is what I mostly wear in the winter.

Best Snow Boots: UGG Adirondack

at Zappos // at Nordstrom // at Macy’s

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 5 or 6 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.

I didn’t buy myself any at the time because I had other snow boots, but this 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.

essential shoes to have in your winter wardrobe: snow boots

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 grass, so they protect my sneakers from getting muddy and keep my feet warm and dry.

Best Sneaker Boots: Sorel Explorer Joan

at Nordstrom // in Grey // at Zappos // Explorer Carnival Cozy // Out N About Conquest

I love a sneaker boot for casual, sporty looks, and I really wish these boots weren’t selling out almost everywhere! They are so lightweight and cozy and soft and warm… all of the adjectives!

essential shoes to have in your winter wardrobe: sneaker boots boots (8) // similar jeans // similar coat // similar beanie

They work great with leggings and skinny jeans, as shown above, or you can slip them underneath straight leg styles. I’ve actually been known to wear these around the house instead of slippers when I’m really cold.

boots (8) // similar jeans // sherpa (S) // t-shirt (M)

Since these boots are selling out everywhere, I’m wondering if they’re being discontinued, and I went ahead and linked a few other options for Sorel sneaker boots above. If you do manage to snag a pair of these, they’re true to size or size down if in between.

Best Leather Sneakers for Winter: Veja Esplar

at Bloomies // at Nordstrom // at Shopbop

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.

Because they’re leather, they protect my feet from the elements, and they have a casual-cool vibe that I love. I’m not wearing socks here, but sometimes I do wear my J.Crew cashmere trouser socks with these.

These sneakers feel stiff at first, but they break in easily and are very comfortable. They run true to size; I am consistently a 39 in this shoe.

Best Winter Flats: Sam Edelman Loafer

at Zappos // at Nordstrom // at Bloomies

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.

The Sam Edelman Loraine Loafer that I linked above is the newer version of the Lior Loafer that I’m wearing here. I just picked up a pair of the Loraine in black because I’ve been wishing I had black loafers in my wardrobe. It’s very comfortable and a good value for the price point. They run true to size; I have the 8.

Best Winter Pumps: Marc Fisher Zala Pumps

at Nordstrom // at Bloomies

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 beige suede.

The pointy toe elevates the look, but the chunky 2″  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?

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16 thoughts on “Essential Shoes To Have In Your Winter Wardrobe

  1. I live in Southern Ontario, Canada so winter footwear is definately essential.
    For me with warm boots they MUST have a zipper. I have a couple of pairs that lace up the front BUT they also have a zipper on the side so the laces are purely for looks…I do not have the patience for tying up laces everytime I”m in and out of boots.Personally I like Rieker/Remonte for looks and warmth. My daughter is a teacher and swears by her LL Bean boots (look similar to the Uggs) for warmth when she is outside on yard duty.
    I also have a pair of the Vessi waterproof sneakers, for warmer but still wet days they are amazing. They also go on every single trip with me, just in case – and they double as a pair of comfy sneakers.
    Often on milder days I will wear sneakers or my Cole Haan loafer/sneakers and just put a pair of boots in the car…just in case. Its a Canadian thing…lol..never leave home from November to April without boots, coat, hat, mitts and scarf in the car.

  2. 1. Library Author Luncheon in mid-April. Would love ideas.
    2. April wedding in DC. Cocktail.
    3. Do you still like the Sam E Agnes booties? They are on sale which is why I’m asking.
    4. College graduation dresses! I have triplets. Will be hot.
    5. Casual dresses for touring Italy in June. Will be very hot. Need at least one dress that covers knees and shoulders although I could bring a wrap for shoulders.

    Yes, my life seems to be back to normal and I’m thrilled to have things on my calendar.

  3. I’ve been living in my Blondo boots since I got them in November, I haven’t even touched any of my other boots which means I’ve got a stack to donate come spring. I’ll keep an eye on those Ugg boots for everyday outside use, currently I’m wearing a pair of boys size 4 snow bootsI grabbed shopping one day because i had literally wore the insole out of my last pair of winter boots last fall. They are black with lime green stiching and they crack me up when I wear them.

    As for events, I’ve got a Tiki dinner I’m going to at the end of February. I do have a couple flowered dresses I could wear or a hot pink sleevelss shell that I might look for a fun floral skirt to go with. It will be entirely up to the weather on if I wear boots or not. Defitnely closed toe. The restaurant did say they wil lbe cranking the heat so I shouldn’t have to worry about a cover up.

  4. I live in colder climate too. I get occasional snow. My favorites are the sorel Joan. I got mine in light brown. Goes with so much of my wardrobe. The other shoe I have is a muck boost. It’s a super heavy duty rain boot. I use for hiking/walking in rain and mud. My dog keeps me honest about getting outside every day so rain or shine I am outside. I have found this good for my body and soul. I am toying with the Ugg snow boots. Your description sounds amazing. And I am not pleased with my snow boots. the price tag is a lot on the Ugg snow boots, hoping they go on sale. I know Ugg doesn’t have many sales so am debating.

  5. Because I wear joggers more than any other pant in my closet, I wear my Birkenstock’s more than anything. I do wear socks with them to keep my feet warm. I have not reached for my knee high boots in several years, which might indicate that I should donate them, but just as soon as I do, I’ll need them. I have a couple pairs of winter boots that I love, but I haven’t needed them this year.

  6. I’m a southern girl (winter down here is only 2-3 months and it’s probably more like what you’d consider fall!) so most of these I wouldn’t get enough wear out of to justify the price. It’s always a challenge to find shoes in the winter for the days when it’s too cold for open toe but not cold enough for warm boots!

  7. I want to add Sorel boots but I like your older style that has the black sole so I never did make the purchase of the black with the white sole…… newer version. They still have my size left too. I just know where I live the white sole will look so dirty in a week. I have a NIke tennishoe boot similar so thinking at this point will wait until next year and see what Sorel puts out. I like your UGG Winter ones but we just don’t get that cold or snowy here. BUT…… when you need them you need them. Great post. You are set.

  8. How do you like the Evereve turtleneck with the stripes across the chest? Thinking of ordering for a trip to wine country in February. Thought it’d be cute for walking around with jeans and sneakers. Is it warm enough to wear without a coat? (Weather will probably be in the low to mid 50s).

  9. I, generally, prefer something not “clunky” (because it, to me anyway, makes driving difficult to judge with too heavy a foot on the gas pedal lol!). So, more like the silhouette of the Blondos or Aquatalias looks cute and lighter weight. Howeverrr: if I feel in the mood for a sweater dress as a work or formal-ish occasion outfit, definitely a knee-length shaft boot (I’ll change into when I’m ready to step out of the car if I’m driving there, ha! — hey: I mention this only because I drive a compact Nissan and not an unwieldy SUV).

  10. I have a pair of black lug sole mid knee boots with buckles that I am wondering how to wear. I used to wear them with leggings or skinny’s which currently I am not wearing and I tried tucking in straight jeans and that looked weird because the jeans bloused at the top of the boot. Any suggestions?

  11. Thank you for this post! I ordered the Sorel Hi-Line Heel Chelsea in the Geo/Yellow Jet Color, and the Sorel Tivoli IV. I also snagged the Sherpa Jacket from Vuori. I love the cut and fit, I would have never picked it for myself, and it’s super cute!!

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