Before I figured out how to style knee-high boots for my personal style, I was certainly guilty of just mimicking whatever was “in” at the time. I looked like a hipster cosplaying Christian Girl Autumn in dark-wash skinny jeans (or leggings) with a boatneck sweater, an infinity scarf, and – you guessed it – a pair of knee-high riding boots. Then, it was the only outfit I knew how to put together with my beloved Steve Madden shoes. And while I’d argue that it still is a tried-and-true look, I’ve since learned there are so many more styling possibilities than whatever I was regurgitating from Tumblr.
The biggest myth around wearing knee-high boots is that they don’t work with a lot of bottoms. I would challenge that they actually go with any bottom, from minidresses to long jorts, midi and maxi-skirts, and more. Just remember to layer up with a trusty pair of thermal tights in order to stay warm and cosy all day.
Whether your personal style leans more preppy, sporty, classic, or anything in between, there are endless iterations of tall boot styles that fit the latest fashion trends and match with your wardrobe. Ahead, find nine outfit ideas and inspo for how to wear knee-high boots, plus more styling tips and tricks to get the looks for yourself using items in your closet.
Featured in this article
- 1. Classic Knee-High Boots & Co-Ord
- 2. With a Turtleneck & Printed Skirt
- 3. With Micro Shorts & A Playful Coat
- 4. With An Oversized Jumper Dress
- 5. Knee-High Riding Boots & Miniskirt & Sweater
- 6. With A Puffball Skirt
- 7. With A Wool Coat & Suede Shorts
- 8. Chic Midi & Oversized Jumper
- 9. Trench Coat
- 10. Tailored Midi & Blazer
- 11. Knee High Boots & Capris
- 12. With A Sparkly Mini Dress
- 13. With Skinny Jeans & A Cropped Jacket
1. Knee-High Boots & Classic Co-Ord
Try out a pair of heeled black knee-high boots with a matching miniskirt and autumn jacket set for a fail-safe outfit. A tall boot is the perfect complement to a shorter-length skirt, and since the top and bottom already match, it’s an easy look to throw on for a night out or a day at the office. Just throw on some sparkling jewellery and a statement bag to round it all off – and don’t forget tights when the cold weather hits. I love chocolate brown tights RN.
2. With a Turtleneck & Printed Skirt
Pointed-toe boots have risen in popularity over the last few seasons, and no one is surprised. The sleek style goes with literally everything. Who said chic had to be neutral? Add a print and a pop of colour to your knee-high boots look for a playful spin on the sleek trend.
Want to take your boots from day to night? Just add a fun mini skirt or skort. Something with texture like appliqué or sequins is sure to make you evening ready. I love to balance out a feminine evening look with a statement wrap coat, or oversized biker jacket. Cool girls, look no further.
4. With An Oversized Jumper Dress
A wardrobe staple for the winter months, jumper dresses are seriously cosy, and look gorgeous paired with any kind of knee high boots. Pick something in neutral hues for a day in the office, or go for something with a bolder tone if you like the sound of making a statement.
After something else? Discover how to style a jumper dress.
5. Knee-High Riding Boots & Miniskirt & Sweater
If you're looking for a failsafe wear to style your boots, let this be your cheat code. A plaid mini, blue shirt and brown knit and you're ready for the office and beyond. This is an outfit formula you can repeat again and again with what's already in your wardrobe.
6. With A Puffball Skirt
Puffball hems are still everywhere, and if you're bored of the classic mini skirt – although that's hard to imagine – opt for something like this Mango one for an easy wardrobe update. This feminine style pairs well with a chunkier boot and leather.
7. With A Wool Coat & Suede Shorts
Mini skirts not your thing? Shorts are just as chic, even moreso if they're suede. Styled, of course, with your favourite shirt and wool coat. When the temperature drops you'll probably want to wear tights too.
8. A Chic Midi Skirt & Oversized Jumper
Not everyone would agree that long boots work with a midi-skirt, but this outfit is a masterclass in sophisticated styling. From satin slips, to more structured pleated skirts, midis always look exceptional when paired with an oversized jumper – while knee high boots are great for grounding the who outfit.
9. With A Trench Coat:
Update your usual camel trench coat this winter season with something two-tone or denim. Obviously we'll be wearing them over everything this season, graphic tees et al.
10. Tailored Midi & Blazer
We told you these boots weren't reserved for short hemlines. Don't overlook your favourite structured midi skirts when it comes to styling your boots. Whether you prefer fitted tailoring or a borrowed-from-the-boys look your maxi-skirt look will be complemented with either.
11. Knee-High Boots + Capris
Don't let yourself be fooled into thinking that you. can't rock a pair of culottes or wide-leg capri pants with your favourite knee high boots. Go for cowboy boots or rain boots, and pair them with culottes and a statement jumper or jacket – maybe in a dark accent colour, like burgundy or plum.
12. With A Sparkly Or Shiny Mini Dress
There's no denying that knee high heeled boots are the ultimate shoe for party season. Go for a hi-shine pair, and couple them with a shiny and colourful mini dress. Bonus point for sequins and sparkles.
13. With Skinny Jeans & A Cropped Jacket
Wondering how to style knee high boots with your old pair of skinny jeans that are suddenly back in fashion? We've got you. We love these Dune chunky boots, paired with Levi's 720 jeans. Be brave. We know you've got it in you.
This article was first published on Glamour US.
