Fall/Winter Fashion
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7 Winter Outfit Ideas with Over-the-Knee Boots

Yesterday during our Facebook Live, someone asked for outfit ideas with over-the-knee boots, and happily that is a post I can easily create with looks from my archives! I actually have several pairs of OTK boots that I rotate depending on the look I’m going for, so I rounded up a few of my favorites here.

7 Winter Outfit Ideas with Over-the-Knee Boots

I love wearing over-the-knee boots. They instantly give a basic outfit a modern vibe, and they’re also warm, which is a plus!

I’ve been asked if shorter women can/should wear OTK boots, and I think most certainly can, but you may want to look for boots with a lower shaft height; they’re not all the same. Even at my 5’5″, I prefer the OTK boots that come just above the knee. I do have a pair that comes up higher, and for some reason they seem to emphasize my hips, so I have to be careful what tops I wear with them.

So here are some of my favorite winter over-the-knee boot outfits from the past few years.

7 Winter Outfit Ideas with Over-the-Knee Boots

#1. grey suede OTK boots + skinny jeans with tunic sweater

These grey suede over-the-knee boots have a 21″ shaft and and a 1″ heel, so they’re very comfortable. The shaft circumference also varies among OTK boots, and these are 14 1/4″ so they’re not as snug as some. If you have bigger calves and don’t like to wear heels, these are perfect for you! I wear them often with jeans and sweaters because they have a more casual vibe. I actually wore them on Sunday (you can see them on my Instagram.)

Also, these jeans are really good for $64, but definitely size down because they stretch some with wear.

funnel neck sweater // Wit & Wisdom skinny jeans // Vince Camuto Kochelda Over the Knee Boots // leather hobo // hoop earrings // similar Maui Jim sunnies

#2. black suede OTK dress boots + tweed pencil skirt with classic sweater

I also like wearing OTK boots with dresses and skirts, and this outfit features a gorgeous tweed pencil skirt. I like how the OTK boots give a modern spin to this preppy classic.

These exact boots are discontinued, and only a few sizes are left at the Rack; I picked them up on an end-of-season sale last winter. I try to buy all my designer shoes and boots when they’re on a really good sale, but unfortunately that often means they’re being discontinued so I can’t link to the exact pair when I wear them in future years. Anyway! Any dressy black suede OTK boot works with this look.

Typically you want about an inch between the hem of the skirt and the top of the boot, but in this case mine just barely meet and I think that’s fine. The back of the boots have a lower shaft than the front, so they only meet in the front.

Stuart Weitzman Alljill Over the Knee Boots (options) // similar black sweater (option) // tweed skirt //  black tights // black satchel

#3. brown suede OTK boots + skinny jeans and olive pullover

This outfit formula is the one I wear most often. Basically any of your skinny jeans with a sweater and OTK boots is going to make a cute, casual outfit.

These boots were a Nordstrom Anniversary Sale purchase in 2017, but I found a few sizes left at Nordstrom Rack. I don’t wear these enough, mainly because the shade of brown doesn’t seem to compliment a lot of my wardrobe, but I’m probably over-thinking it. I definitely gravitate more to greys and black when it comes to my footwear.

I love the more casual lug sole, but I find the higher shaft and the snug fit to be a little harder to wear than some of my other styles.

Here’s a tip for wearing this style boot: I always wear crew socks over my skinny jeans to hold them in place when I pull these boots on, and I find cropped jeans work best because there is less material to contend with in the ankle area.

Stuart Weitzman Elevated Over the Knee Boots (more sizes; other options) // Madewell Northfield Mockneck Sweater // Paige Verdugo Crop Skinny Jeans (on sale here; similar for less) // necklace // earrings

#4. black leather OTK boots + colored denim with moto jacket and scarf

Here’s a blast from the past! I remember shooting this look with Paul and loving how this outfit turned out. Nothing in this picture is currently in stock, so I found some similar items to link.

black OTK boots // similar burgundy skinnies (budget option) // long sleeve black sweater (or sweater) // black moto jackets //  black bag // grey scarf (option)

#5. black leather OTK flat boots + skinny jeans with a classic crewneck sweater and a puffer vest

This was one of my most popular outfits last fall, and this leopard print puffer vest is still fully stocked. Any puffer vest would work, though. A solid color would be just as cute, and you can use any color combo that suits your fancy! A sweater with a puffer vest and skinny jeans looks great with ankle boots, and I wear a variation of that outfit a lot, but the OTK boots give it a little more pizzazz.

These particular boots are from last year, but they brought back a similar style with a slightly lower shaft. I like the leather because I can wear them in any type of weather, and the lug sole makes them easy to walk in. In fact, I wore these walking all over New York City a few weeks ago.

Blondo Olivia OTK boots (similar style) // leopard print puffer vest // Halogen crewneck cashmere sweater (similar option; budget option) // AG legging ankle jeans (more black skinny jeans) // double pearl pendant

#6. black suede OTK dress boots + sweater dress with or without tights

I love tall boots with a sweater dress, and you can wear this look with or without tights. Here is an example of OTK boots with a sweater dress and no tights.

Stuart Weitzman Alljill Over the Knee Boots (options) // ruffle cuff sweater dress // black tights //  layered station necklace

#7. chestnut suede OTK boots + white jeans with a pullover sweater and plaid scarf

This outfit is several years old, but I thought it was fun to include one with white jeans. I always say the key to wearing white jeans for fall and winter is to make them look intentional by pairing them with colors and fabrics that speak to the season. This was fall, so I went with earth tones and cozy knits.

brown OTK boots // Paige Verdugo ankle skinnies (more white skinny jeans) // Halogen crewneck cashmere sweater (similar option; budget option) // plaid scarves

Want to see even more over-the-knee boot outfits? I’ve tagged all of the OTK boot looks in my archives for easy reference.

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18 thoughts on “7 Winter Outfit Ideas with Over-the-Knee Boots

  1. I love how most of your OTK boots come just over your knee and not up to the thigh like some I’ve seen. I guess if you are blessed with really long legs they look good but unfortunately I was blessed with short legs and I never got on the OTK bandwagon. Enjoyed your FB live when I got home from work yesterday. Especially how honest you are about everything from not really knowing what the spring trends will be and how you often just copy other bloggers on what’s trending. Also admitting that the runway styles aren’t for the everyday person. Don’t get me wrong, I love seeing what they (the fashion experts) think will be the new fashion trends but never buy those crazy outfits you might only see on the streets of NYC. 

  2. Love all the looks, especially the dresses. I worry that OTK boots can come off across a bit “Pretty Woman” pre- Beverley Hills makeover 😂 but all of your looks are stylish, elegant and classy. Do you find that the boots irritate the skin around/ behind your knees as you walk, sit, bend?
    Have agreat photo shoot!

  3. Over the knee boots are my fave; I loved this post. I save all your outfits on Pinterest but it was helpful to see several outfits and get the details in one post. Thanks so much!

  4. Looks great on you but don’t think I could pull it off at my age. I am partial to short booties. Especially in south where warmer winters.

  5. At 5’3 I never got on the OTK band wagon. Just not for me and I know I wouldn’t wear them. You however have styled yours with great class and I especially like the leather jacket and white denim and skirt shots the best.
    Have fun with your photo shoot can’t wait to see some of your rooms🤗

  6. Your outfit of tweed skirt with black top & boots is one of my favs. I hope you wore it often because it is an outfit that people will stop to look at, and in a good way. 
    Have fun with your photo shoot! 

  7. Love this post. Breaking from my ample supply of ankle boots & booties I purchased my first pair of OTK boots this season in a lovely black suede. I bought them to complete an outfit (just above knee length dress paired with a long sweater coat). It’s perfect for an upcoming bridal shower lunch and frigid Chicago weather. I’ve been looking for other pairing ideas to get some mileage out of my new boots. This post is very helpful. The tweed skirt, black top & black suede OTK boots is a gorgeous ensemble!

  8. You wear boots so well. I loved all of these looks. I finally gave up on the OTK boots last year. Some bodies aren’t built for them and I had to accept mine was one of them. 😔No worries, I wear flip flops like a BOSS. HAHAHA!

  9. Love, love, love the tweed skirt/black boots outfit, you look gorgeous!! If I was 25 years younger I would have to have that outfit and as your aunt I know you would give it to me! ha! ha! xoxo

  10. Being 4’10, with muscular calves,  OTK boots and I wouldn’t get along.  I even have a problem finding tall boots that don’t turn into OTK boots – and not in a good way.  Ha ha  But, I did manage to find a pair of black and a pair of brown riding boots that aren’t too tall and I can zip them up!  I love your outfit ideas and I can just sub out my tall boots for the OTK boots.  I’m trying to work up my nerve to wear white jeans with them. I have loved your winter outfits with your white jeans.  Looking forward to watching your FB Live today.  I was out of town yesterday.

  11. In your opinion, is there an age when you shouldn’t wear this type of boot? I love fashion and have 3 pairs of OTK boots and I love them but never want to seem like I’m trying too hard or trying to be too young! Any thoughts?

    1. Hey Stacy, I dno’t think so, but I think it depends on the style of the boot and what you wear it with. Also, the quality matters as we get older. I try to wear them with other classic items to keep it classy. Hope that helps!

  12. Jo-Lynne – I loved everything you styled today, especially the moto jacket outfit and the white denim look! I don’t always think of wearing white denim in winter but your look really pulls it together! Great post and so glad I could catch your FBL yesterday- such great information! Enjoy your photo shoot and have a blessed day!

  13. Love, love, love the looks. You wear OTK boots in such an elegant and classy way Jo-Lynne, wow.

    Thank you for all you do to show us how to pair outfits and show it in a classy way. I love all the outfits you showed us today. You look fabulous!!

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