Styling Thigh High Boots

It’s my favourite fashion time of year here in the southern hemisphere – boot season!! And thigh high boots are a big trend for this Autumn and Winter, but I know for a lot of us thigh highs can be a bit scary. If you’re going to rock this boot trend you need to make sure you’re not stepping into “Pretty Woman” territory.

I’ve had this pair of boots hiding in the closet for a while. I bought them with “thigh high” hopes (excuse the pun – but I had to!) but haven’t been daring enough to actually wear them out…until now! I decided it was time to embrace the boot, so I decided to put together some outfits and share my thoughts on styling this trend…

Firstly, I think the key is to remember that thigh boots are already considered to be sexy so you don’t need to show too much skin or wear anything super tight to complete the look. So keeping that in mind, these are the looks I came up with…

LOOK 1: The Conservative Look… By keeping the hemline of the dress a bit longer, and wearing tights underneath, it keeps the look a bit more conservative and with a jacket, this is perfect for chilly weather.


LOOK 2: The Sweater Dress… Well I didn’t have a sweater dress handy, but I did have a cable knit poncho! Sweater dresses are another big trend and they are super comfy and warm.


LOOK 3: Keeping it Casual… Jeans and a sports team t-shirt can be jazzed up a little with a pair of sexy boots. The look is pretty casual but the boots just add a little bit of extra fashion to an otherwise simple look. It was a bit cold so I added a plain black sports jacket and I’m a bit of a ‘cap’ lover so had to include the hat!


LOOK 4: The Chic Look… I love this one, its classy, chic and super cute! I work in an office Monday to Friday and it’s easy to get complacent with fashion day after day. This look is professional but also cute, and you could add a pair of tights or a longer skirt to make it a bit more conservative.


I hope this gives you some ideas to step into a pair of thigh highs this winter!

What would you pair with these boots and what was your favourite out of these 4 looks?


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