How to Wear Over The Knee Boots — 12 Outfits to Copy Right Now!

One of the most common styling questions I get asked is “Can you post more outfit ideas for over the knee boots!?” While I absolutely love OTK boots (and you’ve seen me style them countless times on the blog), I can see how they can be an easy piece to fall into a style routine/rut with! So, I refreshed this roundup of OTKs boot outfit inspiration–pulling from outfits I’ve worn over the years––to get you through the rest of winter and into spring! Let this be your #1 go-to next time you need outfit inspiration and ideas for new ways to remix your favorite pair of OTK boots!

First, let’s talk about my tried-and-true favorite boot styles:

Over The Knee Boot Styles:

Blondo boots: 

My #1 most worn pair of boots––you’ve likely heard me talk about Blondo boots because I feel like it’s ALL I talk about! SO many of you are equally obsessed — they topped the list in our Real Women Approved post on winter essentials! And for good reason as they are all waterproof, which is a game-changer in snow, slush, rain and general commute grime! (You wear them right out of the box, no proofing needed!)

They come in way more styles, not just OTK, but I’ve had my pair for years and they hold up so well, even in the slush! They come out with an OTK version every year, and I recently purchased the NEWEST version so I could review and compare, and I love them even more because the newest pair (called the Presto) has great traction on the bottom! Right now, they’re also 50% off!  Blondo runs true to size in my experience.

Stuart Weitzman Lowland boots: 

The Lowland boots are TOTALLY a splurge, and one of my few designer items. I don’t wear these nearly as often as the Blondo boots, simply because I don’t want to wear my nice boots in crappy weather, but they’re probably my favorite pair of boots I own. They are so high quality and are the only pair I’ve found that TRULY hug my legs. (I have very small child-like calves haha.) These also run true to size.

How to wear over the knee boots for any occasion — 12 over the knee boots outfit ideas:

Over the knee boots with a leather skirt:

Sweater: Evereve, runs TTS!, Coated Denim Mini Skirt: Old, (similar here!), OTK Boots: Stuart Weitzman (also available at Shopbop!)

How cute would this outfit be for Valentine’s Day?! This is one of those outfit formulas that you can really adapt to wear anywhere. If you want to wear it to work, go with a skirt that’s on the longer side. If you want to wear it out for a date or the girls, go with a shorter skirt. The formula is just top, skirt, boots–that’s it! The only thing you want to ensure is that there’s still a BIT of skin showing in between the top of the boot and the bottom of the skirt, otherwise you’ll look a little frumpy.

Over the knee boots for work with a blazer, silk button down and skirt:

Sweater Blazer: J.Crew (TTS), Silk Button Down: Everlane (TTS), Corduroy Mini Skirt: Old, (love this similar Madewell option (50% off right now!) and this one from Topshop), OTK Boots: Blondo

This is a polished look that is great for the office if you work in a more casual environment (I would totally wear this to Equilibria!) If you work in a more conservative environment, you may need a skirt that’s a bit longer, but the outfit formula still works! You can also add opaque tights for the office/cold weather.

Casual Weekend Night Out: Over the knee boots with leggings and a black turtleneck:

Turtleneck: Old, (similar version here that’s on sale!), Faux Leather Leggings: Spanx, OTK Boots: Blondo, Earrings: Old, (loving these similar options here, here & here!)

I think this is the perfect outfit for a night out when you want to be comfy, casual, but still stylish! I think OTK boots with leggings are like PB&J–you just want to make sure that you’re wearing suede boots with faux leather–leather on leather will look too intense.

Over the knee boots with a moto jacket and a mini skirt:

Moto Jacket: BLANKNYC (they have so many great styles and colors right now!), Coated Denim Mini Skirt: (Old, similar here!), OTK Boots: Blondo

One of my favorite style tips: When in doubt, add a suede moto jacket! It adds a great twist to any outfit. Remember the juxtaposition rule? This is a great example of that.

With a bodysuit, cardigan and mini skirt:

Cardigan: Madewell, Bodysuit: (Old, love this similar version too!), Coated Denim Mini Skirt: (Old, similar here!), OTK Boots: Blondo

On the contrary, if you want to dress down an outfit, add a chunky cardigan! The juxtaposition rule wins again! Notice how this is actually the same outfit as the one above–it just looks and feels completely different because I’m wearing a casual, chunky cardigan instead of a leather jacket! Tricky tricky, right? This is a great example of an outfit you could pack on vacation and go from day to night with a quick change of layers.

With a blazer, graphic tee and mini skirt:

Oversized Plaid Blazer: Everlane, Graphic Tee: (My friend Juley’s company, Femme Next Door! They’ll be available soon! I also love J.Crew’s and Sezane’s graphic tees!), Croc Mini Skirt: (Old Topshop, but found select sizes at Nordstrom Rack for a steal of a deal! Runs small–wish I’d sized up to a 4!), OTK Boots: Stuart Weitzman (also available at Shopbop!)

Another blazer, mini skirt and tee combination–but a completely different look than the one above, am I right? This one is definitely more on-trend with a little bit of edge! It’s a great outfit that can really be worn anywhere from brunch with the girls to drinks on Saturday night. (It would also look adorable with sneakers or loafers, too!)

With a cashmere turtleneck and mini skirt:

Cashmere Sweater: Old, (but adore this similar Everlane Cashmere Turtleneck Sweater that comes in 9 colors! Run TTS), Corduroy Mini Skirt: Old, (love this similar Madewell option (50% off right now!) and this one from Topshop), Scarf: Lord + Taylor (20% off right now!), OTK Boots: Blondo

I LOVE mixing hues of brown/tan and black together. (Can you tell?! Haha!) This is no exception. This look is perfect for so many different occasions from day to night. (Which is why some form of this outfit is almost always packed with me on trips!)

With leather leggings and a Barbour jacket:

Coat: Barbour Quilted Beadnell, Cashmere Sweater: Old, (similar here!), Faux Leather Leggings: Spanx, Scarf: Lord + Taylor (20% off right now!), OTK Boots: Blondo, Beret: Halogen

I think a lot of times, we can feel like leather leggings are a bit too edgy, trendy or just “too much”–but this outfit is a good example of how to make them feel preppy instead of trendy. The OTK boots tone down some of the edge (plus, they’re really warm, haha!)

Over the knee boots with a flannel and suede skirt: 

Plaid Boyfriend Shirt: Treasure + Bond, Suede Skirt: Old, (love these similar styles from BLANKNYC), OTK Boots: Stuart Weitzman (also available at Shopbop!)

I love how OTK boots look with suede skirts! And this flannel top acts as a great neutral to pull everything together. This look would actually be adorable for daytime or nighttime!

Over the knee boots with a long-sleeve LBD and statement coat:

Coat: Topshop, Dress: Old, (similar here and here!), OTK Boots: Stuart Weitzman (also available at Shopbop!), Bag: Old, (I love Topshop’s selection of fun purses!)

I absolutely adore a loose, flowy mini dress, and they look ESPECIALLY great with OTK boots for the perfect balance of sweet + spicy! This would also look so cute with a sweater dress. Again, the trick here is to pair OTK boots with a dress that still shows a little skin in between your boots and your dress, otherwise it will look frumpy.

Over the knee boots with a bodysuit and mini skirt:

Bodysuit: Old, (love this similar version too!), Coated Denim Mini Skirt: Old, (similar here!), Leather Jacket: Old, (this great Amazon steal is very similar!), OTK Boots: Blondo

Black on black with black boots is a no-brainer. This is such a great go-to date night look! If it’s feeling a bit too much for you, you can add a jacket in a contrasting color! (Yes, you can wear brown with black!)

Over the knee boots with leather leggings and a tunic:

Clearly this is a combo I wear often 😂

Turtleneck: Dudley Stephens (full review here!) Faux Leather Leggings: Spanx, OTK Boots: Stuart Weitzman on the left (also available at Shopbop!), Blondo on the right Scarf: (Old, similar styles here), Beret: Halogen

This is another great example of the juxtaposition rule––a little classic/cozy/feminine and a little edgy with the faux leather––it just works! Add OTK boots to a tunic and leather leggings combo in the winter/cold months to polish off a look, not too mention add an extra layer of warmth!

I hope this gives you new wardrobe inspiration and many ways to shop your closet with OTK boots!

You might also like — The Comfiest Shoes I Own!

Looking for more outfit ideas? Right this way!