Knee-high boots are a divisive wardrobe staple. So, you just got a new pair of knee-high boots, and you’re not sure what to wear them with, what is the best match? Whether you’re a fan of the style or not, there’s no denying that they can be a bit tricky to style.
You can wear knee-high boots with skirts, dresses, and skinny jeans. It all depends on your fashion taste, occasion, and what you have at your disposal.
In this post, we’ll give you some tips on what to wear with knee high boots going out so you can rock the look no matter where you’re going.
What to Wear with Knee High Boots Going Out
Knee-high boots not only keep you warm, but they also look great. Since the height is slightly higher than other types of footwear for women or men, they ensure that you’re not left feeling chilly on those cold days, and their classic style makes them an easy choice for any event or occasion.
Below are some outfits you can look good wearing with knee-high boots when going out.
1. Skinny jeans
There’s no need to worry about your outfit when wearing the perfect skinny jeans. These versatile garment fits like a glove and can be styled with anything from t-shirts, tanks, or blouses. You’ll find yourself reaching for these classic blue or black denim items because they blend well with knee-high boots.
2. Sweater Dress
If you want to be cozy and warm simultaneously, there’s nothing better than wearing a sweater dress with knee-high boots.
Sweaters are available in different lengths, so make sure that whichever one fits well will also complement your figure. A more extended size would probably suit most people better if they prefer extra warmth during freezing weather.
Pairing these outfits together is an easy way to get stylish while staying comfortable. Grabbing knee-high boots in a color that will match your favorite sweater dress is always wise.

3. Plaid Skirt
The plaid is a great print that’s mostly worn during the fall. It’s fun and youthful, perfect for those looking to add some color into their wardrobe without going too far outside of style norms. Pair this outfit together by wearing your knee-high boots, and you’ll be sure not only look good but feel fabulous too.
4. Shift Dress
Knee-high boots are a great choice to wear with your shift dress. The garment will hug every curve and does not dictate age. Shift dresses are something that you can either rock as is or take up to a higher level with accessories such as knee-high boots. The looseness of the shift style makes it flattering on everyone, no matter what shape your body might be.
Also read: Best thigh high boots that stay up
5. Asymmetrical Skirt
Knee-high boots are the perfect addition to any outfit including an asymmetrical skirt. Not only will they keep your feet warm and dry, matched with knee-length skirts with an asymmetrical hem, but they can also give you a chic fall look that could easily take on different styles from casual office attire up through formal events.
The best part? One side does indeed cover some aspects of this decorative footwear while leaving other sides exposed.
6. Pencil Skirt
If there is one type of skirt that will make you look like a model, it’s the pencil. The flattering cut and slimming design alone can take any outfit from ordinary to extraordinary.
It highlights your hips and gives you a smaller waist, which looks great when paired with knee-high boots.
7. Maxi Dress
The maxi dress is a wardrobe staple for every woman. It’s easy to transition into fall by simply wearing your favorite piece with some knee-high boots. The extra warmth from these types of footwear will make you feel cozy, while the dress will feel comfortable and stylish with your knee-high boots.
8. Knee-length Dress
Dresses are the perfect item to wear in both summer and winter. They’re light enough for warmer weather and offer some coverage when it gets cool out – especially if you throw on a pair of knee-high boots.
Also read: Top-rated snake proof boots
Outfits to Avoid When Wearing Knee-high Boots
1. Loose or Baggy Pants
The perfect outfit starts with the proper footwear. If you have knee-high boots, wear them only when paired together carefully to avoid creating an awkward look for your clientele or peers.
If you wear your knee-high boots with the wrong type of pants, it will make a confusing figure that’s not sleek or fashionable.
Choose skinny jeans or leggings to fit in seamlessly with modern trends for best results.

2. Tights and Shorts
The combination of knee-high boots and shorts or tights is still popular, but it’s an outdated look that can be difficult to pull off. If you really love this style, try wearing mini dresses instead.
Also read: Can you wear boots in hot weather?
Frequently Asked Questions
What Can I Wear with Knee High Boots Going Out?
Knee-high boots are not just for the winter. You can wear them with any outfit, no matter what season. They’re perfect to transition into springtime because they offer warmth without being too bulky or heavy. The knee-high boots are ideal for adding height and complexity, perfectly matching with dresses, miniskirts, and skinny jeans.
Is It Ok to Wear Knee-High Boots in Summer?
Knee-high boots are perfect for any season including summer and can be worn year-round. Pair them with a cute outfit to take you from fall through winter into spring. Keep it basic with jeans and sweaters for a cozy thatch look, or try knee-high boots paired against fitted shirts for an edgier vibe.
Knee-high boots can be a versatile addition to your wardrobe. Whether you’re dressing up for a night out on the town or just want to look your best for an upcoming holiday party, they can add a touch of glamour to any outfit. It’s important to know what outfits to wear to make the most of this style.
We’ve put together a few different looks for you above to look stylish and confident when heading out. Feel free to choose from any and rock them with your pair of knee-high boots.