Shoes can totally make or break an outfit, but in the winter shoes can feel especially tricky. You need them to be practical for the weather AND look good with your outfits. The problem is many women don’t actually have the right options in their closet, so things start to feel complicated, like you’re constantly trying to force outfits that don’t quite come together. The good news? Just a few key pairs of winter shoes can cover all your bases, keep you comfortable, and make it easy to feel pulled together all season long!
Today I’m sharing my must-have shoes for the winter, including pairs that are comfortable, versatile, weather-appropriate, and stylish. These shoes will work for your everyday outfits and simplify style so you can feel pulled together effortlessly. If your winter wardrobe ever feels like it just needs a little nudge to come together, these shoes can help!
SIZING: I’m 5’6” and usually size S/M or 6 in clothes and 8.5 to 9 in shoes.
1. Water-Resistant Casual Boot
A water-resistant boot like this is perfect for casual outfits, such as sweatshirts and casual sweaters paired with jeans. Plus, being water-resistant means no need to change shoes or overthink your outfits if it’s wet outside!
This style is SUPER versatile. The tall and narrow shaft ensures they work EFFORTLESSLY with ALL cuts of jeans, from slim straight jeans to bootcut to wide legs. This is why you absolutely want this style in your closet as a wardrobe essential!
The pair I’m wearing is no longer available, but there is a nearly identical pair HERE with great reviews.
Shop the Outfit:
Jeans: Quince (wearing size 28)
Sweater: Kohl’s (wearing size S)
Boots: Nordstrom (similar)
Necklace: Nordstrom (similar)
2. Water-Resistant Casual Boot – Lug Sole
Another option that I personally love are these Naturalizer boots. They have a thicker sole and chunkier profile, which I think works better with chunkier sweaters, as the chunkier profile of the shoe balances the chunky sweater. If you had to choose between this pair or the pair above as your go-to casual boot, I’d go for the previous pair as the slimmer profile automatically looks more polished. But I personally wear this pair more because of my super relaxed style! These are water-resistant as well and come in more colorways — another reason you might want to add these as a second casual pair.
Unfortunately, the color I own is no longer available, but several other colorways are available. I’ll link to four places they’re available because the stock and color options vary, so this will help you find what you’re looking for: Nordstrom, Zappos, Amazon, DSW.
Shop the Outfit:
Sweater: Gap Factory (wearing size S)
Jeans: Gap Factory (wearing size 8/29)
Boots: Amazon
Necklace: Nordstrom (similar)
3. Elevated Casual Sleek Boot
If you’re looking for an elevated casual boot — one that’s not as casual as the Chelsea or lug sole boots I shared above, but not quite dressy (like the ones you’ll see below), you’ll want an elevated casual sleek boot like this one or like this one. Both of these styles hit that perfect in-between note that works with nicer sweaters and jeans, relaxed work looks, and blouses and jeans.
Courtney recommends this water-resistant pair to a lot of our members — she owns it and likes it a lot.
As for the second option, one of our PMT Style Club members, Kristy, shared these in her search for low-heeled, comfortable, but polished boots. Kristy’s style is more elevated, even her casual outfits, and this type of boot is great for that elevated casual style and can transition to some dressier outfits as well!
4. Water-Resistant Dressy Boot
I’ve shared about these boots a ton, but they really are just so versatile and make looking good EFFORTLESS. Like, truly. The shaft is tall and narrow, so they work with even the slimmest straight leg pant, plus your flares, wide legs, and boot cuts. They also look great with dresses and skirts. The style is sleek and versatile, so they look polished. And, they have a square toe, which is so important in adding that sharpness and polish to outfits. You could also go for a boot with a pointed toe, but a lot of you say that pointed toe shoes feel too dressy for everyday life — and I feel the same. A square toe tones it down but still adds the sharpness and polish to your outfits that a round toe doesn’t. Plus, these are water-resistant, so you never have to worry about changing your shoes last minute when it’s wet outside.
I know these boots are on the pricier side, but they seriously make it effortless to look good. They strike the perfect balance of dressy but not overdressed, and anytime I find that balance in a piece, I consider it a gem not to be overlooked. You can find all the color options HERE. I own them in two colors, black and tan, shown above. I wear size 9.
Shop the Outfits:
Black Sweater: Quince (wearing size S)
White Sweater: Target (wearing size S)
Jeans: Quince (wearing size 28)
Necklace: Nordstrom (similar)
Boots: Nordstrom (wearing size 9)
5. Pointed Toe Dressy Boot
If you have the previous pair of boots, you might not need these pointed toe dressy boots. BUT, I like to have them as the ultimate dressy boot that you can wear with ANY outfit to dress it up. The kitten heel and pointed toe add sharpness and polish, big time. The tall shaft makes it easy to pair with every style of pants, skirts, and dresses. This is a classic style that I’ve worn and recommend to everyone as a go-to dressy boot that will come in handy whenever you need to dress up, for years to come. Find them HERE. I wear size 9.
Shop the Outfits:
Green Floral Blouse: Kohl’s (wearing size S)
Jeans: Kohl’s (wearing size 6)
Dress: Amazon (wearing size M)
White and Black Blouse: (similar)
Cardigan: (similar)
Burgundy Pants: Gap Factory (not available in this color – wearing size 6)
Boots: Target (wearing size 9)
6. Tall Boot
I wouldn’t say this is a must-have, but if you need a tall boot, here’s one I recommend to look effortlessly polished. They pair well with flares and wide leg jeans, and they work beautifully with skirts and dresses. This style has that perfect balance of sharpening up an outfit without looking extra. The pointed toe is really important to not looking dowdy and feeling more polished and pulled together, especially if you are going to wear it to dress up. Also, it’s water-resistant. Truly, this style is one you can wear now and for years to come! Find it in two colorways HERE.
7. Lifestyle Sneaker
If you can wear sneakers in the winter where you live, then of course I’m going to tell you a lifestyle sneaker is a must-have! A great pair of lifestyle sneakers is KEY to looking polished and pulled together in casual outfits. Wear them with ALL of your casual outfits that include jeans, sweatshirts, t-shirts, and casual sweaters. Bonus points if you have a pair with a sleek enough design that you can also wear them with dresses and skirts.
There are several styles to choose from, but the ones I recommend are:
- this pair with a gum sole — I’ve owned these for a long time and love them.
- this pair with black accents — I now own these too!
- a clean, all-white pair
- super-affordable pair
Shop the Outfits:
Long Sleeve Tee: (similar)
Vest: Amazon (wearing size S)
Jeans: Quince (wearing size 28)
Sneakers: Walmart (wearing size 9)
Sweatshirt: Amazon (wearing size S)
Leggings: Amazon (wearing size M)
Sneakers: Zappos (wearing size 8.5)
These pairs of shoes are the workhorses that will carry you through the winter season and instantly make outfits feel more polished while being effortlessly versatile to throw on. Remember, you don’t need every single one of them, so figure out which ones you need for your lifestyle and start with those. I hope this list helps massively simplify your winter shoe lineup!
Which of these do you already own? Would you add any to this list?
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