One of the most common styling questions I get asked is “Can you post more outfit ideas for over the knee boots!?” While I have a TON of outfits I’ve worn on the blog with my favorite OTK boot styles, I don’t have them all in one place–so I thought it was time to change that 😉Let this be your #1 go-to next time you need outfit inspiration and new ways to remix your favorite pair of boots!
First, let’s talk about my favorite boot styles:
Over The Knee Boot Styles:
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 are all waterproof–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! The pair that is closest to mine is this pair! Blondo runs true to size in my experience.
Steve Madden OTK boots:
The tan pair of boots you’ll see below are Steve Madden. Again, they’re an older pair, but this pair is super similar and is on sale for $77! They also come in black! Steve Madden in general 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 bodysuit and mini skirt:
This is a look you guys have seen most recently in my “How to wear all black” post! Black on black with black boots is a no-brainer. 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 a leather skirt:
Stuart Weitzman Lowland Boots–huge splurge, but they’re my favorite boots that I own! However, I do wear the Blondo boots more often simply because they’re waterproof and in the Chicago weather I don’t have to worry about ruining them! Old sweater (it’s convertible to off the shoulder!) but similar sweater here. Leather skirt is also old, but this BlankNYC one is similar and they are my favorite skirt brand! (Same brand of every other skirt I’m wearing here haha!) Madewell Transport Tote (I also have the zip-top version which I got more recently, and I prefer that version for the added functionality!)
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:
This is one of the outfits from my Fall Capsule Wardrobe – if you haven’t seen it yet, you’ll definitely want to download my free 30 Days of Outfits guide! This is a polished look that is great for the office. Of course, if you work in a more conservative environment, you may need a skirt that’s a bit longer–but again, look at this outfit as a formula, not quite so literally! That said, I would HIGHLY recommend both the Everlane silk button down and J.Crew Sophie blazer to add into your workwear rotation (you’ll wear them a ton outside of work, too!)
Casual Weekend Night Out: Over the knee boots with leggings and a black turtleneck:
Similar black turtleneck, leather leggings–I also love this pair! (If you’re in between sizes go with the larger size). Blondo waterproof suede boots (mine are from a couple years ago but these are similar! Old earrings–but similar here!
Forgive the Christmas tree in the background of these next couple outfits, haha! They were from my NYE outfit ideas post (but definitely check it out for lot’s of Date Night outfit ideas across the board!) 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:
Another outfit from my non sequined NYE outfit ideas post – one of my best 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:
On the contrary, if you want to dress down an outfit, add a chunky cardigan! The Juxaposition rule wins again 😉Notice how this is actually the same outfit as Outfit #1 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 just a change of layers.
With a cashmere turtleneck and mini skirt:
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:
Blondo waterproof suede boots (mine are from a couple years ago but these are similar! Plaid scarf (looks like Burberry but is $30!!) black leather leggings, Black Barbour coat–other colors available here!
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 are the perfect footwear of choice (plus, they’re really warm, haha!)
Tan over the knee boots outfits:
Over the knee boots with a dress and leather jacket:
Leith ruched t-shirt dress (I’m wearing a small here–if I wanted it tighter I would’ve gone XS, FYI, for size reference) They come in a TON of colors, sleeveless and with sleeves, and regular and plus size! Similar blush jacket (this one is old but this is the new version! Runs TTS!) Very similar OTK boots on sale here for $77!! Beret
If you do not yet own this dress, do yourself a favor and go snag it right now! You’ll wear it for SO many occasions, all year long. From date nights with heels to baby showers with flats to running errands with sneakers–this dress does it all. It especially looks cute with some OTK boots and a leather jacket. You guys often ask me for ideas on stylish outfits you can wear to more conservative occasions (like showers, church, etc) and this is definitely one of them!
Over the knee flat boots with jeans:
Sometimes the best thing to pair with your OTK boots is good old fashioned, classic skinny jeans, a t-shirt, and a sweater! It’s a combination you can always count on, and one that will always be polished!
OTK boots with a sweater dress:
Sadly this sweater dress is very old (linked a couple similar above) but I think OTK boots and a dress are always a fool proof combo. You know what I’m going to say (because I’ve said it a lot above) just make sure the hemline is above the boots and that there’s a bit of skin showing through in between–otherwise it will feel frumpy! You can honestly make this look work with ANY dress!
Over the knee boots with a floral blouse and white jeans:
Very similar OTK boots on sale here for $77! White Madewell jeans (run TTS! The best white jeans!), old top from LOFT, but if you’re looking for a cute floral top I lovethis one , this one, and this one –they’re all on sale and and they would all look super cute with this outfit!
And for seasons like this one, where you are DYING to wear something springy but it’s still freezing outside–I offer up this outfit combination to steal. Tan over the knee boots with with white jeans and a floral top. White jeans always put a fresh feeling spin on any outfit, and it’s a great hack to feel springy and warm at the same time.