As we think towards cooler temps, winter dressing can be tough, especially with the shoes! Today I’m sharing five must-have winter shoe essentials that will make it effortless for you to pull together outfits, even when it’s rainy and cold.
Have you ever put together a great outfit, glanced down, and realized your shoes don’t go with ANY of it? 😅 Winter makes this worse, because now your shoes might also have to handle the cold and the rain.
The good news is you don’t need a closet full of shoes to make it all work! A handful of versatile styles can cover pretty much everything, from casual everyday outfits to work, dinner dates, and dressier occasions.
Choose the ones that make the most sense for your lifestyle and the weather where you live.
SIZING: I’m 5’6″ and usually S/M or 6 in clothes and 8.5 to 9 in shoes.
1. Casual Boots — Chelsea Boots or Lug Sole Boots
First, you need a good pair of casual boots for colder days! Chelsea boots and lug sole boots are both great options.
If possible, look for a water-resistant pair! Then, you won’t have to change your shoes—or rethink your entire outfit—just because it’s raining. Anything that makes getting dressed easier is a win in my book! 🙌
Also, choose a pair with a tall shaft that fits closely around your ankle, which will be the MOST versatile. This style works well with pretty much ANY type of pants, from wide leg to slimmer straight fits. And the taller shaft makes it work effortlessly with ankle-length jeans and full-length jeans alike. With this style, you won’t ever worry about whether it fits with your pants!
For a more relaxed look, go for a chunkier lug sole style. The ones I wear are no longer available, but they are similar to THIS pair. I love how well they pair with chunky sweaters, slightly oversized sweatshirts, and puffer jackets.
If you prefer more tailored looks, go for a more streamlined boot, like THIS one or THIS one.
Shop the Outfits:
–Black Sweater (wearing size S)
–Grey Sweater (wearing size S)
–Cuffed Jeans (wearing size 28)
-Boots (similar, similar)
–Black Necklace (get 25% off!)
–Hoops (wearing size 30mm)
–White Earrings
Shop Casual Winter Boots
BTW, several of the boos up there are from Nordstrom Rack, which is SUCHHHH a good place to shop for shoes! They have the awesome brands I love from Nordstrom, but for LESS. You NEED to be shoe shopping there if you aren’t already!
2. Elevated Casual Boots — Sleek Ankle Boots
Next up are boots that are a little more polished than your everyday casual boots, but not so dressy that you can’t wear them regularly.
These are great for elevated casual outfits, like jeans and a nice sweater and a blouse, or even a casual dress. They instantly make an outfit look sharper without feeling totally overdressed.
The Nordstrom Alida boots are my go-to’s. They’re sleek and streamlined, so they go with pretty much everything, from elevated casual outfits to slightly dressier ones, including workwear. The square toe adds polish but isn’t too angular, and the block heel makes them sturdier and easier to walk in.
AND they’re WATER-RESISTANT! I LOVE that you can wear these with a nice outfit and not have to change your shoes if it ends up raining. Perfect mix of practical and polished!
Also, I don’t know why, but what looks like the same pair under a different name (the Etana) are ON SALE HERE!
Shop the Outfit:
–Sweater (wearing size S)
–Jeans (wearing size 28)
–Boots (wearing size 9)
–Hoops (wearing size 30mm)
Shop Elevated Casual Boots
3. Dressy Boots — Sleek Boots With a Sharp Toe
For even dressier winter outfits, you’ll want a pair of sleek boots with a sharper toe and a more refined heel. As much as I like the Alida boots above, to really make dressy outfits polished, you need a sharper toe.
I’m wearing this pair in the second outfit above. This style has been my go-to dressy option for over a decade. It never fails and NEVER goes out of style! Don’t let the tiny heel fool you — it’s low, so it’s quite easy to walk in.
Shop the Outfits:
–Dress (wearing size S)
–Boots (wearing size 9)
–Hoops (wearing size 30mm)
I also have this pair from Sam Edelman, which is another good option. The toe is square instead of pointed, and the heel is easy to walk in. The chocolate brown suede is beautiful, especially for this season! But, it comes in black leather and burgundy leather as well.
Shop the Outfit:
–Shirt (wearing size S)
–Jeans (wearing size 28)
–Boots (wearing size 9)
–Hoops (wearing size 30mm)
4. Loafers and Modern Flats
On milder days, flats are still an option. I especially recommend loafers and simple flats with a modern silhouette.
These Crown Vintage loafers have a streamlined shape that makes them really easy to wear with both casual and work outfits. They also have some cushion in the footbed, which is always a plus!
Shop the Outfits:
–White Button Up (wearing size S)
–Printed Button Up (wearing size S)
–Cuffed Jeans #1 (wearing size 28)
–Cuffed Jeans #2 (wearing size 6)
–Shoes (wearing size 9)
–Hoops (wearing size 30mm)
Another option is a simple flat with an updated cut, like a V-cut or higher-cut vamp. I have this pair from Nordstrom, and I LOVE how the higher cut gives them a modern silhouette. It’s such a small detail, but it makes a big difference in how fresh and current an outfit looks!
Both are great options when you want something polished but don’t feel like wearing boots or heels.
Shop the Outfit:
–Top (wearing size S)
–Jeans (wearing size 28)
–Shoes (wearing size 9)
Shop Loafers and Modern Flats
5. Lifestyle Sneakers
Last but definitely not least, you NEED a great pair of lifestyle sneakers to wear with jeans and athleisure outfits! Make sure they have a streamlined silhouette for the most versatile, modern, and easy-to-wear look.
One of my favorites is the Puma Palermo sneakers. Besides the sleek silhouette, I love how the gum sole and black accents give them extra character and ground them more than all-white sneakers. PLUS, there’s memory foam in the footbed, so they’re comfy, too! 🙌
Shop the Outfits:
–Sweatshirt (wearing size S)
–Trousers (wearing size M — SOOOO COMFY!!!!!!!!!!!)
–T-shirt (wearing size S)
–Jeans (wearing size 28)
–Sneakers (wearing size 9); also HERE in more sizes
Shop Lifestyle Sneakers
Honorable Mention: Tall Boots
If it’s colder where you are, or because they’re trending again, definitely add tall boots to your list! I’m wearing THIS pair above, which are slim and streamlined. They’re modern and timeless at the same time. I have a style almost identical to this from nearly 10 years ago (in black) and they fit right into today’s styles.
I also own THIS pair, which is much pricier, but it’s also good. Reviews on it are crazy because of sizing. You can find even more sizing options HERE, including narrow calf, standard calf, wide calf, and extra wide calf. I have size 9 in standard calf. The calf is not as slim as the pair I’m showing above, but nothing egregious. 😄
Shop the Outfit:
–Dress (wearing size S)
–Boots (wearing size 9)
Make Winter Outfits Easier With the Right Shoes
There you go! Those are my 5 must-have winter shoe styles for looking pulled together without a lot of effort.
Start with what you already own, then think about which type of shoe would fill a gap in your wardrobe and make your everyday outfits easier to put together.
If you need more help figuring out which shoes work with your jeans, check out my posts on How to Wear Shoes With Different Jean Cuts and How to Wear Boots With Different Cuts of Jeans. The little details can make SUCH a difference!
Which of these five winter shoe styles do you wear the most? And is there one you need to add to your wardrobe?
