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Dress: SheIn Sweater Dress c/o (similar, similar)
Gray OTK Boots: Stuart Weitzman ‘Highland’ in londra medium gray (go down 1/2 size, this one on sale!, similar, more affordable option)
Bag: Grey Velvet Crossbody (similar, splurge)
Earrings: J.Crew Hoop Drops (old, similar)
Over-the-knee boots are my obsession and they are hands-down my most-worn shoe style once the weather cools down even the slightest! I’m pretty much always looking for an opportunity to wear my gray OTK boots so I wanted to share this recent chic yet comfy look. I love the versatility of this dress and it’s the perfect length to pair with gray OTK boots as it hits right above where the boots end. The material is a light waffle knit and the top opening is stretchy so that it can be worn one-shoulder or even off-shoulder! The waist belt gives it some shape and I love the cuteness of the bow — plus it makes this one-size-fits-all dress fit even on someone who’s petite (I’m only 5′!).
Meanwhile my favorite gray OTK boots from Stuart Weitzman were just marked down so I thought I’d share a few ideas on how you can style your very own gray OTK boots! Read on for 12 more outfits (12!) featuring different ways I’ve paired over-the-knee boots as well as my favorite picks if you’re looking to pick up a pair to style this season too!
Dress: SheIn Sweater Dress c/o (similar, similar)
Shoes: Stuart Weitzman ‘Highland’ in londra medium gray (go down 1/2 size, this one on sale!, similar, more affordable option)
Bag: Grey Velvet Crossbody (similar, splurge)
Earrings: J.Crew Hoop Drops (old, similar)
otk boots I love:
Sweater Dress
left to right
outfit 1: plaid dress (similar, similar) | chestnut otk boots | clare v leopard satchel (similar) (original post)
outfit 2: teal sweater dress (similar, similar, similar) | leopard belt | highland otk boots in nutmeg (similar – on sale!) (original post)
outfit 3: blanket scarf | sweater dress (similar) | chestnut otk boots (original post)
Of course let’s start with sweater dresses as it’s the star of today’s post as-is! I love the ease of a one-and-done dress and pair it with over-the-knee boots to look chic and glam all at once! The key to styling this look is to keep the length of the dress short enough to let the tops of the boots still peek out as the hint of skin helps distinguish the dress from the boots. A few of my favorites are in the widget below (I just bought this white one and love it!):
Poncho
left to right
outfit 1: colorblock poncho (similar, similar) | burgundy otk boots (similar)| long-sleeve top | prada bag (similar – on sale!) (original post)
outfit 2: floppy hat | ruffle tiered poncho (similar) | striped turtleneck | skinny jeans | flat otk boots (similar) | leopard clutch (original post)
Ponchos come a close second to sweater dresses for me when it’s time to get dressed and I need something in a pinch! Put on a t-shirt, jeans, and throw on a poncho with over-the-knee boots for an outfit that looks effortlessly glamorous! The over-the-knee silhouette pairs perfectly for creating an elongated leg line that perfectly offsets the volume of the poncho. I was wary at first thinking that a poncho would overwhelm my petite frame, but paired with skinny jeans and a skinny fitted pair of over-the-knee boots and it’s a look that will actually give the illusion of a few extra inches! A few of my favorite ponchos below:
Oversized Sweater
left to right
outfit 1: lace-up sweater | white jeans | nutmeg otk boots (similar – on sale!) | crossbody bag (similar – on sale!) (original post)
outfit 2: v-neck tunic | blanket scarf | distressed jeans | flat otk boots – on sale! (similar) | crossbody bag (similar – on sale!) (original post)
outfit 3: choker sweater (also here) | distressed jeans | buckle belt | lowland flat otk boots in walnut (on sale in praline!, similar) | crossbody bag (similar – on sale!) (original post)
I live in oversized sweaters and blanket scarves this time of year and it’s just so cozy to bundle up in something big, soft, and warm. To keep it from looking like I literally rolled out of bed though, I pair my sweaters with a slim pair of over-the-knee boots and it’s like magic how it all just pulls together! And if I’m not in the mood for tall boots, flat boots work just as well here although I’ll do a little front tuck with my shirt just so it doesn’t look like I’m being swallowed up in fabric! A few oversized sweaters I have my eye on:
Mini / Skater Skirt
left to right
outfit 1: pink coat | white top | camel mini skirt (similar, similar)| nutmeg otk boots (similar – on sale!) | gucci marmont bag (original post)
outfit 2: plaid shirt – on sale! (similar) | gray skater skirt | highland boots in topo suede (similar – on sale!, similar – under $100!) | tory burch bag (original post)
outfit 3: striped sweater (similar, similar) | suede mini skirt (similar)| lowland flat otk boots in walnut (on sale in praline!, similar) | mustard velvet crossbody – on sale! (original post)
Probably one of my favorite pairings is an otk boot with a flirty mini skirt! This is a perfect date night look that looks sleek and sexy yet will still keep your legs warm and toasty. I personally only let an inch or so of leg peek out from above the boots and usually will choose boots in a color that closely matches or complements the skirt just to keep the outfit looking cohesive. A few mini skirts I found and love:
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And now for this week’s On Trend Tuesdays linkup! Sandy and I are excited to feature Sarah from Sew Sarah R this week. She’s sharing the perfect holiday look and some festive booties!

Now it’s your turn to share a recent outfit with the rest of our community for a chance to be featured! Just link up a recent outfit and remember to include either the button below or link to both me and Sandy in your post. We’d love if you could comment on 5 other bloggers too as this is a community where we can all get to know and support each other! Tag us on social media too to join the conversation with #OnTrendTuesdaysLinkUp!
I have always been terrified to try over the knee boots cause of how short I am but this post gave me so much inspiration to try them!
yay!! that makes me so happy!! otk boots are surprisingly flattering even for petites! I’ve personally found that the more lower-priced options have a thicker fabric and end up making my short legs look even shorter. The more high-end boots have a more sleek fabric that hugs your leg and actually makes them look slimmer! The closest dupe for the Stuart Weitzman boots is this pair (with the biggest difference being that the toe is a bit more rounded instead of almond shaped): http://amzn.to/2nrLx4T
hope that helps and thank you so much for commenting!!
xo,
kileen
A beautiful and stylish outfit 😉 Those OTK boots are perfect with your outfit!
https://4highheelsfans.wordpress.com/2017/12/01/league-of-extraordinary-heels/
Oh, look at all the pretty outfits! I am currently obsessed with OTK boots myself. In fact, I just order like 6 new pairs from Shoe Dazzle! My husband may kill me when that box arrives! Thanks for sharing so much outfit inspiration so I have some new ideas to style me boots.
Shelbee
http://www.shelbeeontheedge.com
I love over the knee boots and have several pairs. I just got a pair of burgundy and can’t wait to style them. I love how you styled your burgundy boots. All your looks are perfect!
Cheryl
I can’t live without my OTK boots! They are the best!
Oh my goodness, so many cute looks! I LOVE all the ways you styled OTK boots. You certainly do know how to wear them!
I absolutely adore my OTK boots! I have been trying to figure out other ways to style them, so this is so helpful. Especially loving the look with the skirt!
I love the OTK boots with the shorter skirts, it’s such an amazing look! I love them with oversized sweaters, I feel warm and cozy!
I am a HUGE fan of OTK boots and wear them with almost every fall/winter outfit! I’m loving all of the ways you styled yours!! xo Kimmie
Love all these ideas on how to style otks!
Belle | One Awesome Momma
love all the ways you styled your boots!
I totally live in my OTK all winter long! Love your tips on how to style them!
xo, Steph
http://www.urbanblonde.com
Wow, alot of work went into this post! Such gorgeous looks! I have several pair and have yet to style them with jeans. I do love the look, but really love your grey monotchomatic sweater dress look, gorgeous!
Enjoy your day!
jess xx
http://www.elegantlydressedandstylish.com
Classy look and pretty!
Okay, I am seriously bookmarking this post! I’m always looking for new inspo for styling my OTK boots!
x, B || http://www.brianaanderson.com
You can rock the OTK boots like no other! I love all your looks!
http://www.mylittlenest.org
Over the knee boots are the best! I love your collection of OTK boots and how you styled them!
http://www.rdsobsessions.com
Love this dress with the these boots!!
This is such an awesome post! All of your styles are perfect. People are always asking me how to style these. They are so fun.
xo,
Steph
@trendyinindy || trendyinindy.com
I love OTK boots with sweaters and dresses!
I’m loving your grey sweater dress along with your OTK boots! It’s so perfect and comfortable to wear to work❤️
You’ve definitely given me a new way to style OTK boots. I love your looks!
I love styling mine with mini skirts and sweater dresses. You’ve great styling options here, thank you 🙂
xx
Iliana | http://www.sophisticatedfashionista.com
There are so many cute looks here! I love them all!
We are scarf twins! I have the same plaid scarf that you are wearing with your wine/burgundy sweater dress! OTK boots are such closet staples. I love at how it elevates at look within seconds. Great styling tips! Hope you are having a great mid week so far.
http://www.littlemisscasual.com
Love over the knee boots! You style them so well!
http://www.thefitbrunette.com
I actually have such a hard time dressing up my OTK boots because of my petite frame. This looks great on you!
Aww, thanks so much for featuring my look! XO
I love all of these looks and all of your OTK boots!
xx, Elise
http://www.sparkleandslippers.blogspot.com
The over the knee boots look just perfect with the sweater dress! Loving this!
Thanks for linking up!
OXOX
Dawn Lucy
https://fashionshouldbefun.com/
Thanks for linking up to Top of the World Style. You look stunning in the gray dress with the OTK boots.
Love these OTK boots! There are so many ways to style them!
~Jessica
Jeans and a Teacup
I love over the knee boots and these are just too stylish and elegant. I prefer at work and at leisure too, they transform your personality and look.
This looks really nice on you. I love your fashion sense.