OutFIGHT of the Day: how to wear over-the-knee boots

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Do you still find it pretty impossible to figure out how to wear over-the-knee boots? 

I remember a few winters ago, when the over-the-knee boot bug was biting everyone around me, I swore I would never be able to wear a pair. They always sent me flying back to Julia Roberts’ character in Pretty Woman and I was certain that I would go down the same outfit road should I attempt a look with them.

Well, the boot bug just kept biting and managed to entice me to want a pair. I tried on several, but always ran into one of two problems: styles with high heels made me feel vulgar, while the flat variety combined with my short legs made me look like a midget in boots.

Finally, the fateful wardrobe-changing day came. I was walking down the streets of New York when I spotted platform heeled over-the-knee boots in the window of an Aldo store. It was love at first sight! 

I took them home and we’ve been inseparable since. They’re an integral part of my winter days and I often want to put together an outfit that includes them. I ask myself how they would look with this or that piece and before I know it, and OutFIGHT is taking shape. 

And that’s what happened here today – I wanted to wear my dress/skirt/suspenders (call it what you may) and I immediately thought of the boots I love so dearly. Let’s do it?! 

I’ve been known to wear the thing with nothing but a full-coverage, cute bra that allowed the cutouts to shine in all their glory, but this is a winter look were talking about, so I decided to give an actual shirt a shot. I went for my go-to black crop top but I definitely did not like how all the different shapes and cuts looked together.

how to wear over the knee boots

I decided to try a cropped tee instead, and picked out my kitty cropped from Urban Outfitters because it’s been too long since I’ve worn it and its cuteness made m miss it! hahaha! Cuteness factor aside, though, it really didn’t work out. It’s loose all over and extra fabric stuck out from all sides. 

how to wear over the knee boots

And then I had an epiphany (well, ya know): why not wear the cropped tee over the thing? I figured it’s short enough that the cutouts would still show, but I was clearly mistaken and once again it felt all wrong. Sorry kitty shirt, not this time. 

how to wear over the knee boots

Then I decided I’d just forget about  wearing a top and a jacket and just go for something long-sleeved. For this, I picked out my long-sleeve striped American Apparel crop top, and loved it! The stripes worked really well with the horizontal cutouts and still left a little bit of skin to show. Perfect. 

how to wear over the knee boots

Finally, I put on the boots to see if it really worked and I loved the look!

how to wear over the knee boots

I finished everything off with a bucket bag from Fendi, Arezzo and Tiffany rings and a few from my personal collection and Asos earrings. All the details are in the gallery below:

This is what the final look came out like:

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I’m wearing: 

Urban Outfitters dress
American Apparel crop top
Aldo boots
Fendi bucket bag
Arezzo rings
Tiffany ring
Asos earrings

So how about you, girlies? Did you also go through a major rejection phase before falling crazy in love for over-the-knee boots? Tell me!

Leave your comments below and if you like this post, share it!

Oh, and check out previous OutFIGHTs of the Day by clicking here!

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