I like the look of over-the-knee boots but sometimes it’s hard to wear them and not look a little like Pretty Woman. For most of us, that’s not the effect we’re going for. Elly, from one of my street style posts, knows how to work the look. She wore wedge heels, thick tights, and a flowing boho dress.
Another way to wear OTK boots is with jeans. I kept my look casual by wearing flat-heeled tall boots.
Top: Express
Jeans: The Gap
Boots: Cri de Coeur
Cuff: Craft Fair
These boots are versatile because I can fold over the cuff and turn them into regular knee-high boots. I lose the studs that way, but it’s still a nice option. I bought these on sale from a local shop that is unfortunately not open anymore. Luckily, I can still shop online.
With an OTK boot, I think it’s best to keep the rest of the outfit relaxed (like Elly’s loose dress or my simple jeans). I’d probably steer away from a dress so long that it covers the tops of the boots. Part of having tall boots is showing them off! Plus, a bit of leg shape is nice. Notice that I said leg shape. Tights or jeans are still good to wear. If you have a bare leg with a short skirt and tall boots, a flowy dress and shorter heel is the best way to work the right proportions.
Do you ever wear OTK boots?
I’ve joined Visible Monday today. Check out what other bloggers are wearing.
jeanofalltrades 
I don’t have any OTK boots, but you are inspiring me – these look so smart. I have to check out that site! Thanks for sharing with Visible Monday.
Thank you! These are my first pair. I thought they’d be too OTT (over the top) but I found ways to wear them!
Funny you should ask! I bought some (they are pleather) and I wore them for the first time in my recent post!
http://fashionableover50.wordpress.com/2013/12/14/covered-perfectly-a-rave-review/
Yours look great with studs!
Wow! I was so focused on your tops that I didn’t notice your boots! Love who you wore yours with black pants!
Mine are faux too. Cri de Coeur is an all-vegan company.
Don’t let the Pretty Woman comparisons for OTK boots sway you at all. There are all kinds, and yours look sweet and casual and cool. The boots I’m wearing (in my Visible Monday post … the second one) are OTK, but they’re suede and have stretched so much they fall below the knee nowadays!
I just checked out your boots! Love them. So tall. Even scrunched a bit, they’re high. If they weren’t OTK to begin with, they’d be booties by now! LOL! You’re so right about there being all kinds of OTK boots. It’s impossible to generalize!