How to Wear Over-The-Knee Boots

Sharing the BEST over-the-knee boots that are under $100! Plus, I’m showing you exactly how to style them this season! It’s style for a steal this week on Pursuing Pretty.

Over-The-Knee Boots Under $100

In order from left to right, top to bottom:

Sam Edelman Peyton Tall Taupe Boots $44 |Steve Madden Giselle $84 | Jessica Simpson Leopard (also in black) $90 | Elinna Boots in Black $43 |

Ruvonenn Black Boots Knee-High $69 | Little Burgundy Riley Knee-High Boot $74 |

Adivan OTK Boot in Taupe $69 |Marc Fisher JayWalk Studded Boot $84 | Sam Edelman Vivica Tall Grey Boots $49 |

How To Wear Over-The-Knee Boots

Friends, I can’t deny it, I LOVE OTK boots! But they can be tricky to style correctly sometimes. I’m wearing the Elinna Boots ($43) from Aldo although I have a hard time keeping them up! They fit best when I wear them over jeans or tights or with really thick knee-high socks like I’m doing here. If you’re worried about fit when purchasing online, take a moment to read the customer reviews. You’ll get a good idea of how they fit (too loose, too tight) or if they actually stay up.

Fit:

Over-the-knee boots can be tricky as every pair fits differently around the calf and thigh. If you have slim legs, suede boots may not be the best option for you. They aren’t formed so it’s easy for them to slide right down your leg. You don’t want them to end up looking like a slouchy pirate boot! Choose a boot with a little more structure, like these Sam Edelman ones in my previous blog post. Trying boots on in-store may be the right move if you have time.

Heel:

If you don’t love wearing heels, then these boots may be perfect for you. OTK boots lengthen your legs without actually adding height. A chunky heeled style adds a little height without compromising on comfort. Stiletto heeled styles make me think of Julia Roberts in Pretty Women but they don’t work well for us Canadians during the snowy, icy winters! Don’t forget to add a spray protector on your boots before wearing them in the elements.

Colour:

Black is obviously the most slimming colour and helps to make your legs look elongated. Light grey and beige have also become really popular this year! These boots instantly add an element of chic to an outfit. It easily dresses up a casual look!

Clothing:

Wear your OTK boots over tight-fitting jeans, pants, leggings and pantyhose. I love the look of these boots with a short, mini skirt and a bulky sweater in the winter! Be careful about the length of your skirt. You want to have at least 3-5 inches between the hem of your skirt and the top of your boot. Stay away from knee-length skirts when wearing these boots. Layer with a longer trench coat for a more polished look!

Height:

If you’re on the shorter side, then opt for a knee-high boot instead. I love the two styles that I linked above, the Ruvonnen and the Riley. These will still give you a high boot without being TOO high! You don’t want a boot that covers your entire leg!