Shorts and over-the-knee boots. At the surface it sounds like a recipe for recreating Julia Roberts’ iconic outfit in Pretty Woman, but if you dig a little deeper, you’ll see there’s great potential for a cute outfit that is far from coming off risqué.
I have been obsessed with these Jessica Simpson over-the-knee boots since I spotted them on the clearance rack at Dillards for ONLY $25 (they retail at $150!)! Now that it’s officially fall but not quite feeling like fall here in Dallas, I figured I could go ahead and break out these tan suede boots with this casual cut-offs and plaid shirt look. I had to buy this red, white and navy plaid shirt I found at T.J. Maxx because hello, it’s really cute, AND I know I will be able to wear it so many different ways throughout the year (and who doesn’t love buying pieces that you know you’ll get good wear out of?).
 
 
I think the key to wearing shorts with over-the-knee boots is keeping your top half covered. What do you think? Will you be rocking over-the-knee boots this fall? Check out some of my favorites at the links below!
 
Shirt: T.J. Maxx $19.99 // Shorts: H&M $19.99 // Boots: Jessica Simpson (purchased on clearance at Dillards!!) // Bag:Â // Earrings: Forever 21
Hands down my favorite look of the day!! The boots paired with the plaid is serious fall perfection! -xx
Shauna
http://www.lipglossandlace.net
Oh thank you so much!! 😀
You are gorgeous!! I really love how you styled this outfit and the boots definitely do not look risqué. 😉
Hannah Shanae
hannahshanae.com
I still have never owned a pair of over the knee boots but I love the idea. I just don’t know if I myself can pull it off, but you’re totally rocking it. I love the photos in this post and you look fantastic! xx, adaatude.com
Cannot believe you got those boots for only $25!!! What a steal!
http://www.amemoryofus.com
I can’t wait for the cooler temps this weekend, even at 80 degrees as a possible sign fall is on the way. Love the OTK boots! Cant wait to break out mine!!
http://alwayzfashionablylate.blogspot.com
I absolutely love that your over the knee boots are wedges! This is such a cute casual early fall outfit 🙂
those are a steal!!! i love OTKB, especially pairing them with shorts/skirt.
elle
Southern Elle Style
can’t wait to break out my boots too! love this plaid top & the shorts!
xoxo. | cymone.
The Block is Haute
So darling! I love this country chic look! Those shorts are perfect and I love them paired with the boots!
Sportsanista
You look so pretty in plaid! And I’m so into over-the-knee boots these days— how amazing that those boots were such a steal!!
xo, Christina
Fashion & Frills
You are so cute wearing this!! I love this plaid shirt! I debated all last year whether to get some OTK boots or not. I’m thinking that I should this year! Love how you styled them!
XOXO
Katey
http://www.twopeasinablog.com
Thanks for joining our Tuesday Fashion Party Link-Up!
I really love the color of your hair! I can’t wait to start wearing my over the knee boots…I love the color of yours!
Love this outfit, I am definitely going to recreate this for the transition months! Obsessed with anything plaid and over the knee boots!