Aritzia Skirts & Chloe Woody Outfit

Style Edit

How to Wear Over the Knee Boots in 2022


Over the knee boots were originally created as a man’s riding boot in the 15th century. But now they are one of my cult favourite wardrobe staples!

I have been a fan of over the knee boots for a very long time. Even though knee high, loose fitting boots have been the favourite this year I still can’t stay away from over the knee boots. I think when it comes to trends you just have to give things a try and then stick with what you know and love. And most importantly what makes you feel amazing! Here are some suggestions on how I’ve been styling my over the knee boots this season and how I plan to keep styling them in the future.

Below you will find every outfit that is outlined in my YouTube video above as well as links to where you can shop similar items online.

STUART WEITZMAN Genna stretch-suede over-the-knee boots


Genna stretch-suede over-the-knee boots


Chloe Woody Tote


Medium Size


TIGHTS: more opaque seamless & sheer seamless

Aritzia Skirts & Chloe Woody Outfit

Outfit #1

White Ribbed Turtleneck

Midi Check Skirt *Similar Vibe

Option 1

Option 2

Option 3

Clueless Inspired Outfit

This is the first outfit I put together when creating this post. I was thrilled with the gorgeous richness of the boots and reached to the back of my closet to find a skirt I hadn’t styled in eons! This outfit is very much serving me Clueless vibes mixed with a long fitted blazer. Things one might not notice necessarily in an outfit like this is a pop of gold, the crisp white turtleneck and a curled under hair style. I can definitely see myself grabbing for this when the temperatures warm up again!

The One I Could See Rachel From Friends Wearing

When looking into style inspiration for 2022 a huge trend this year will be Y2K fashion. Even though this isn’t everyone’s cup of tea we can still embrace this kind of trend in our own way. I really see outfit two as a “Rachel from Friends” inspired look. This outfit truly makes me feel like I am playing a character who isn’t necessarily me and I love it!

Rachel but make it Festive

I know we’ve already covered Rachel Green but I just can’t help but to think of her every time I see a fitted mini skirt. This is why I love blogging and shopping my own closet. It gives me an opportunity to try different combinations. Who said you can’t wear a mini in winter! By adding on a chunky knit and some tights this outfit becomes a little more facetted for cooler weather! Now I have to admit I haven’t worn this combination just yet but come the spring I am going to give it a go!

How to Wear Over the Knee Boots in 2022

Outfit #3

Chunky Turtleneck

(Cream Camel Colour – 16 options)

Sunday’s Best Mini Skirt (Blue Gingham)

Cozy and Cute in a Sweater Dress

Okay give me a star for at least trying on this one. I have never been one to shy away from wearing black and brown together but I have to admit I think this look might have been even better with a truly chocolate brown belt or a black belt. When colour blocking I really try to stay to 2 tones. However it’s not all together horrible and at least gave me a chance to see what this sweater dress belted might look like. With all of this being said I am still so in love with the oversized sweater dress and think it certainly has a place in everyone’s wardrobe!

Chic and Date Night Ready

Do you see what I mean!? (In comparison to the outfit above). Keeping this entire look within the two tones completely elevates it overall. I am so in love with this dress from Oak + Fort. I purchased it fall 2020 online and really think it highlights the best bits of me. We all know I love a mock neck/ turtleneck and this short sleeve number certainly does the trick with a midi-maxi length. The slit up the leg is a perfect pairing for a little peek-a-boo over the knee boot! The chef’s kiss! xo

A Sweater Dress but Make it Creamy

Over the last bit I have been doing some major wardrobe recon. I have been purging the pieces that truly do not serve me or my style anymore and I have been sticking to a colour palette when purchasing new or pre-loved.

Cream is a big part of this palette. I believe I purchased this gorgeous sweater dress from & Other Stories last winter and am finally getting around to styling it. Keeping in mind we aren’t exactly out and about just yet I need to commit to wearing this more. I am giving this outfit high praise for the quality and the fact that it is truly following the guidelines for where I want my style to go!

A Classic Everyday Favourite

If we are on the topic of wardrobe staples let’s include some more shall we! The white shirt and a good pair of jeans cannot be missed in a capsule wardrobe. All of these together are a simple everyday uniform!

I wanted to elevate this look a little more and add some warmth for those cooler months. Adding a blazer to this looks shows how easy it is to achieve both of these things. This look is a little equestrian and a little business woman and I am digging it.

My Winter Uniform

If we ever happen to cross paths during the winter months I can almost guarantee I am going to be wearing an iteration of this look. A chunky knit, hoop earrings, pair of jeans and a stylish pair of boots (fingers crossed haha!). I love this look so much and truly it’s my go-to!

An Old Favourite

As soon as I put on this outfit I have to admit, it felt like stepping into an older version of myself. I still love this kind of outfit formula but I really think I am moving into a new style decade. An oldie but a goodie!

New Flavour of the Month

I know I already mentioned the joys of shopping my own wardrobe to find new combinations and this outfit is exactly what I am talking about. I have loved this vegan leather shirt/dress for so long but I simply had no idea how to style it. By mixing things up and grabbing some style inspiration from my friends we have landed on this cute outfit. I have to say I am so excited to get to go out with the girls again so I can rock outfits like this!

Thanks for following along – I’d love to hear your thoughts on the OTK boot trend and if you are already participating or you are considering it for next fall/winter season. I think next season I’m going to invest in another pair of a lighter shade! Slowly growing the wardrobe of my dreams!

Much love,

Amanda xo

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I'm Amanda – blogger, content creator, photographer,  videographer,  and founder of Below the Blonde: a space for vibrant, ambitious women who are looking to live their best lives in style.









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