Thigh High Boots: 30+ Dresses To Pair With Them

Have you ever stopped yourself from buying a pair of thigh high boots because you don’t know what you would wear them with? Well, that ends today. 

Thigh High Boots 30+ Dresses To Pair With Them

We are going to show that just in the category of dresses, there are over 35 different styles you can wear thigh high boots with. 

Let’s jump straight into the list. 

1. Monochromatic Sweater Dresses

If there is ever a perfect time of the year to wear thigh high boots – it’s the fall. If you want to stay warm but look glamour you should consider wearing a sweater dress that perfectly matches your boots. 

2. Amber Dress With Matching Scarf

Speaking of fall, who doesn’t love an outfit that will make you crave pumpkin spice lattes just from looking at it. We love the combination of cool-toned boots with a warmed-toned dress. 

3. Silk Oversized Shirt

We love a silk shirt with any outfit, so we are not surprised that we love this combination. You cannot go wrong with oversized shirts. The jewel-tones in the first make the similar tones in the boots really sing.  

4. Floaty Floral Dress

If you need the perfect outfit for a spring date then look no further – this outfit is it. We love that the boots match the base color of the dress too. 

5. Summer Dresses In Fall Tones

We love the light summer fit of this dress paired with the deeper shade of mustard yellow. To make it even better, the boots come in a complementary tone of yellow. 

6. Sleek Pinafore

 If you do not have a sleek, black pinafore dress in your wardrobe then you need to rectify that right now. Not only do pinafore dresses look stunning with thigh high boots, but they also look great with nearly every type of shoe. 

7. Floral Maxi Dress (With Shiny Boots)

This suggestion is as much about the amazing latex boots in this image as it is about the flowing, floral maxi dress. We love the juxtaposition of the pair. 

8. Shapeless Mini Dress (With Slouchy Boots)

If you have the confidence, why not rock an 80s inspired look and pair a pair of slouchy thigh high boots with a slouchy, shapeless but comfy mini dress. 

9. Simple, Plain Dress (With Animal Print Boots)

 This crisp white dress, with clean and straight lines, looks amazing when paired with these snakeskin thigh high boots. A dress like this would look good with any kind of animal print boots. 

10. Off The Shoulder Mini Dress

Thigh high boots are often worn to show off a bit of skin on your legs, why not pair that with a dress that shows a bit of skin too. Off the shoulder dresses pair beautifully with these types of boots. 

11. Long Coat, High Boots

If you want to feel like a model walking around Greenwich Village during fashion week then you are going to want to try out this look.  

12. Low Cut Dresses

Early we talked about showing off skin while wearing thigh high boots. You can also do this by wearing a low-cut dress that shows off some decolletage or cleavage. They won’t know where to look. 

13. Bright Suede Boots With A Dark Coat

We challenge you to look at this image and not want to replicate it immediately. We want to and we’re in the middle of doing something. This shade of blue is perfection. 

14. Tight Lace Dress

We love how the plain, dark, thigh high boots only make this dress look more glamorous. Wearing a pair of black boots is a great way to tone down a bold look. 

15. Figure Accentuating Wrap Dress

Tight thigh high boots make your legs look both longer and slimmer. So why not add to the illusion and pair these boots with a wrap dress that makes you look like you have the perfect hourglass figure. 

16. Cut-Out Suede Dress

We are obsessed with the shape of this dress, and the little cut-outs on its shoulders only make this look sexier. We also love the way that suede dresses hold their shape throughout the day. 

17. Animal Print Dress (With Plain Boots)

We said we love a plain dress with animal print boots, so it will be no shock to you that we love an animal print dress with plain boots – especially when the look is monochromatic. 

18. Denim Dress With Chunky Belt

You get bonus points if you can get a belt that matches your thigh high boots! But in all seriousness, this is a look that you can rock from early spring all the way through to late fall – and know that you look great. 

Did somebody say, cowboy?! 

19. Turtle Neck Chunky Knit Dress

Do we really need to say anything about why this is such a good look?! 

20. Blazer Dress

You do not need a Channel belt to pull off this look, but a gorgeous blazer dress will help. If you love showing off your hips, then this will be a great look for you.  

21. Casual Plaid Oversized Shirt

This is the same concept as the silk shirt we were talking about earlier but it’s more pumpkin patch than it is fashion week. That’s not to say that this outfit isn’t adorable – because it most definitely is. 

22. Leather Boots With A Leather Jacket

You’ll want to pair this look with a simple dress but putting leather boots and a leather jacket together is always a win. There is no way to look bad when you are rocking this combination. 

23. Monochrome Outfit With A Contrasting Long Coat

This outfit has everything going for it – a matching dress and shoes, snakeskin pattern, and a matching bag too. But what really makes this look so special is the long coat that clashes with it all. 

24. Trench Coat Dress

Trench coats (despite their reputation) somehow many to toe the line between classy and sexy. We think that they look best with a black or brown boot, but honestly, you could pair them with any color. 

Keep your accessories simple with this look and try to match them to the color of your boots. Don’t forget about your watch. 

25. Simple Dress, Big Bag

If you have a really cool bag that is too big or too bright for you to pair with any look then try it out with this suggestion. Take a simple oversized shirt dress, or a skintight dress and layer the bag over that. 

26. Body-Con Mini Dress

If you are hitting the clubs then you might want to try out this really simple look. A super tight dress with tight thigh high boots. 

27. Hoodie Dress

If it is good enough for Ariana then it is good enough for us. In this look, she is matching her hoodie with her boots, but you could try rocking any combination of colors.  

29. Body-Con Maxi Dress With Slit

This looks gives us witch on the way to ruin her ex’s life vibes and we adore it. This is a perfect look for fall that you could wear to the coffee shop, to dinner, or to a house party. Pair it with a big hat and a vampy lip and we would never want to take it off. 

29. High Neck, Mod Rocker Dress

Channel the 60s with this cute dress and boot combo. 

30. Big Shoulders, Tight Boots

 We love this very high fashion looking dress with the intricate pattern across the chest and shoulders paired with the simple and tight thigh high boots. The boots elevate this elegant look even more. 

31. Sports Jersey Dress

Sometimes there is just no getting out of wearing a sports jersey to an event. But that doesn’t mean you have to let the jersey swallow you and your fashion sense up. A belt, a nice clutch, and a good pair of thigh highs will fix that in no time. 

32. Matching Two-Piece

We know that including a two-piece set in this list is cheating a little bit – but look at that outfit, we couldn’t just ignore it. 

33. Winter Look

We are completely obsessed with this coat and dress combination – and the inclusion of thigh high boots sends this look off the charts. Our life goal is to be able to stay warm while looking good. 

34. Let The Boots Steal The Show

Sometimes, it’s not about the dress you are wearing – instead, it’s all about the boots. If you have a pair of boots that you want to show off to the world – then wear them if they make you happy.