How to Wear Over-the-Knee-Boots and Not Look Like a Street Walker

I've always been intimated by over-the-knee-boots, afraid that I would like Julia Roberts character in "Pretty Woman." At the beginning of the season I made it my mission to find an affordable pair, after seeing some of my favorite bloggers, like Liz of Late Afternoon and Helena of Brooklyn Blonde, rocking them. I figured I needed to kick the fear, so I first started by trying on a different boots even some that I knew I couldn't afford. Which was a totally heartbreaking when I found a pair of soft grey suede Jimmy Choo over-the-knee-boots at Century 21. But I finally found my pair a couple of weeks ago at Aldo. With the right price tag and months of searching I knew I had to take the plunge. So here I am playing dressing up and figuring how not to look like a street walker. Here are a couple of key ideas.

For the Weekdays:

 

Dress: Artzia (old) | Jacket: Zara | Shoes: Aldo | Bag: Marc by Marc Jacobs | Scarf: c/o Hugssy | 

Bracelets: Bauble Bar and c/o Ann Taylor | Sunglasses: No Names

Fitted + Tight = Street Walker.
Flare + Cut high enough just to show a sliver of skin = Chic.
Keep dresses and skirts pulled away from your body. Fit and flares are flattering on all body types, it really enhances your curves. If your boots cut up right above the knee or a little higher pick a dress or a skirt that short enough to show just a peek of skin. A darker colored dress will also keep the look chic. When pairing up with a jacket or coat pick one that is also a little longer, this will help play with lengths and keep you looking long. Keeping accessories to a minimum bracelets and scarves are perfect little accessories that can enhance the look. PS stay away from red lips. If you are a lipstick wearer, especially like me a sucker for richer colors, swap it out for a pink lip.

For the Weekends:

 

Coat: H&M (old) | Sweater: LOFT | Leggings: American Apparel | Shoes: Aldo | Bag: 3.1 Phillip Lim X Target | 

Hat: Glow Accessories

all pictures taken by Brian Cavanaugh

Darker bottoms that can blend in with your boots are preferred. When wearing leggings, keep them a basic black and wear with a chunky sweater or longer tunic. Things that are a little longer, chunkier, or adding layers will help keep from being overly flattering. I know what a backwards thought?! You don't want to look to sexy, just subtle sexiness. Do a nude lip for a laid back look. This look if perfect for Sunday brunches.

What do you think of over the knee boots? Will you be wearing them this season?