kourtney kardasian and random fashion blogger in oversized tops and thigh high boots

5 Ways to Wear an Oversized Top + Thigh High Boots

Is she wearing shorts under there? Here are five of the best oversized sweaters and over the knee boots this fall.

Thigh high boots plus an oversized sweater, hoodie or top works well from day to night. This outfit has been spotted on celebrities such as Ariana Grande, Kourtney Kardashian and Lindsay Lohan. People will ask if you have pants on. But you will be too cutting edge to care!

Both over the knee boots and comfy sweatshirts tend to be wardrobe staples during the fall and winter. These fan favorites are comfortable, fun to wear and they match everything. Accessorize with a long ponytail, clutch, choker and/or statement earrings.

1. Steve Madden X Willow & Paige

Steve Madden Isaac ($109.95) Willow And Paige Oversized Sweater With Tipped Ruffle Trim ($60)

This sweater available from ASOS has the high neck with a ruffle trim AND an oversized appearance. It is paired with the new Isaac boots by Steve Madden that are in a grey velvet perfect for fall and winter.

2. Nasty Gal X H&M

Nasty Gal Pop Up Thigh-High Boot ($120) + H&M Oversized Denim Shirt ($34.99)

Nasty Gal recently debuted a slew of thigh high boots in eye catching prints and colors such as hot pink, metallic silver and mermaid. And this season H&M is betting on basic oversized hoodies and tops.

3. Topshop X Wildfox

Topshop Boxer Thigh High Boots ($190) + Wildfox Mirage Spell Sweater ($180) 

It’s difficult to pick just one oversized top by Wildfox, but this one has a fun 80’s throwback appearance. It would go well with these Topshop boots that have the coveted cone heel and slouchy look.


YEEZY Season 4 Stretch Canvas Thigh High Boots (On sale for $386) + FENTY PUMA BY RIHANNA Oversized Hoodie (On sale for $165)

Go completely street fashion on their ass by wearing both FENTY and YEEZY together in an outfit that screams Top 40 hip hop music. Those sneaker head, label whores won’t know what to do next!

5. Saint Laurent X Alice & Olivia

Saint Laurent Niki 105 Boots ($10,000) + Baron Velvet A-Line Hooded Dress ($330)

When you drop ten grand on a pair of sparkly over the knee boots you don’t need a lot of extra accessories to go with them. This black velveteen hoodie is simple yet soft and luxurious.

To look sexy and be comfortable up in the club or out in the street go with a trusty pair of thigh high boots worn with an oversized top.

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Elizabeth de Moya has contributed to DJ Mag, DJ TechTools, LA Weekly and Thump (Vice). She has a BA in Linguistics from UC Berkeley.