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

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.

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. 

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. 

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. 

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

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:

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!

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

Kisses! ?