How to Wear Tall Boots

Tall boots can look chic and attractive when worn correctly. They are modest yet sexy, and can be a wardrobe statement piece. Slender, snug boots make your legs look especially long, and when paired with skinny bottoms and a loose top, the elongating power of the boot is only amplified. Whether you go for a conservative English riding style boot, sexy bright red clubbing boots, or cowboy boots, these are a great addition to a woman's wardrobe.

Part 1

Part 1 of 3:

Showcasing Your Boots

1
Show off your thigh-high boots. These boots, because they are dramatically tall, will be a focal point of an outfit. They will bring attention to your sexy lady legs.
- Tall boots, especially over the knee boots, are most dramatic paired with a short skirt or with slim-fit pants.^{[1]XExpert SourceVeronica Tharmalingam
  Professional StylistExpert Interview. 6 April 2021.} You can use them in other ways, such as under a long skirt, but the effect is not as dramatic.
- If you want to tone down the sexiness of the boots a little simply overlap the skirt of your dress with your boots about one inch (or three centimeters). Be sure to stick with plainer colors and embellishments. A sophisticated pair of tall, tan leather boots is less in-your-face sexual than a bright red, shiny pair of night clubbing boots.
2
Pair with leggings or tights. Pair your thigh-highs with opaque tights, leggings, or nylons. These often slenderize and shape legs, and in colder weather help your legs feel warmer.
- Pair brightly colored or interestingly printed leggings with black or brown boots, because attention will be drawn down to your legs, your leggings, and your boots.
- Wear a less intense pair of leggings or tights with a more exciting pair of tall boots (boots that hit your calf, or your knee are both great for this).
Advertisement
3
Wear skinny jeans with tall boots. Tuck your jean leg into your boot to show off the full height of the boot. Skinny jeans hug your legs. As a result, they work with your boots to make your legs look long and slender.
- Avoid tucking in loose or flared jean cuts, such as "boot flare" or wide pant legs. These may bunch up if tucked into your boots.
- You can wear tall boots in wide or "boot flair" pants, however, you will be showing only the lower part of the tall boots.
4
Pair your boots with a miniskirt. You can either pick a more subdued mini-skirt, in brown or black or grey, or you can go all out with a neon blaze of color. You can successfully give the illusion of showing a lot of leg without actually being scantily clad.^{[2]XExpert SourceVeronica Tharmalingam
Professional StylistExpert Interview. 6 April 2021.}
- Be careful of how strong your overall impression is giving. A very short skirt with tall boots may not be appropriate for a professional office, even if you are not actually showing anything inappropriate. You may be better off with a more conservative just-above-the-knee length.
- Wearing opaque with your mini-skirt and boots adds a touch of class to your cute outfit and will also keep you warmer if it's fall or winter.
- Going without leggings or tights creates a more daring look, and shows off your legs. This is a great look for going out at night, or in warm weather.
5
Glam up your weekend boots. If you want your boots to be the focal point of your outfit for a night out at the dance club, choose tall boots in exciting colors, textures, embellishment, and otherwise draw the eye.
- You will need to decide what is fabulously over-the-top and what is just ridiculous. This will be different for each woman. One woman will love her crimson stiletto-heeled boots with lots of metallic chains. Another woman may find it quite silly.
- If you can walk in them (and make sure you practice before going to the club) try out some high stiletto heels with your knee-highs. They are basically guaranteed to draw the eye, especially if you pair them with a little dress, or skirt.
- Metallic studs, chains, cut-outs in the material of the boot are all interesting additions to a pair of boots.
- You might also try out exciting colors. While these are a little more difficult to pull off in the day, they're great for a night at the club. Crimson, bright purple, even yellow are all interesting colors that draw the eye.
Advertisement

Part 2

Part 2 of 3:

Incorporating Boots into Your Outfits

1
Wear you knee-high boots for work. Tall boots can be a refreshing change from flats or high heels. Be sure they are sophisticated and modest for your office, and leave the shiny, loud ones for the weekend.
- Pair with fall-ready textures like tweeds, wool, and cashmere, like a knee-length tweed skirt and a cashmere sweater. These all make for subtly stylish work or school attire.
- You could also pair your knee-highs with a pencil skirts and tailored shirt. Toss on a cardigan for the cooler months.
2
Temper the over-the-knee style. The over-the-knee boot can be great for showing off your legs, but be sure that your boots do not overwhelm the outfit. If in doubt, go with a longer skirt and use tights or leggings.
- For a sophisticated, conservative look, try various shades of brown or black in natural-looking leather. Keep bright colors, patterns and finishes for more casual moments.
- Wear a long skirt, to shin or ankle. This covers up the boot, only showing part of it, while giving you the warmth and protection of the over-the-knee boot. But it does give you another way to wear your boots.
3
Wear riding boots. There are two different types of riding boots: Cowboy boots, and the English style riding boots. Both types can help foster a great casual look for your outfit.
- Both best with sleek lines (like skinny jeans or leggings ^{[3]XResearch source}
- Cowboy boots can be a very regional fashion trend. For example, it may be common in Texas, USA, but seen as acceptable but perhaps rather quirky in Quebec.
- For a subtly Western look pair cowboy boots with sleek trousers or skinny jeans (distressed jeans are particularly good) and a blouse.
- You can also do leggings and sweater/sweater dress for a good fall fashion.
- Riding boots, especially cowboy boots, can go a long way towards toning down a really feminine dress. They can help balance out a really frilly or flowery dress, an especially good look for spring.
4
Pair jeans with any boot. Jeans are often a good choice to wear with boots, because they can be dressed up, or dressed down, depending on the boot. You can show-case the boot (as described above with skinny jeans) or you can downplay it (wearing boot cut jeans that cover the boot).
- A great casual look for fall or winter is a pair of distressed skinny jeans with slouchy black suede boots and a chunky cable-knit sweater.
- A nice looking blouse paired with sleek suede or leather boots and dark narrow jeans is a dressier look (and good for a first date!).
- The only boot that does not usually work with jeans is the thigh-high. Thigh-high boots tend to go best with short skirts or leggings.
Advertisement

Part 3

Part 3 of 3:

Choosing the Right Boots

Some boot styles are meant to have some slouch, but for most tall boots, you want to avoid pairs that gape around the top. Your boots should fit snugly yet comfortably. There should be enough room to tuck in skinny jeans or leggings, but not enough for your leg to slide back and forth inside the boot.
This is especially true for women who consider their legs to be one of their problem areas. If you have thicker thighs, avoid boots that reach up to your mid-thigh. The horizontal line across the top will only make your leg look wider. Instead, opt for knee-high boots or boots that rise just above the knee.
3
Choose a boot that works well with your height. Tall women can get away with heeled and flat boots of all sizes. Shorter women may wish to stick with heeled boots, especially those that have a skinny heel, since these help to elongate the leg.
- Shorter women should also stick with snug boots that closely hug the leg. Looser boots may make a leg look stouter.
- If you are shorter, remember that proportions matter. Pair a tall pair of boots with tucked in jeans and a short jacket. If you go for a long jacket, like a trench coat, you're going to be completely swallowed up.
4
Choose the right color. It can be a little difficult to pick the right colors, because boots come in so many different shades! However, there are some things you can consider to help you figure out which colors work best with your hair color and with your choices of outfits. Grey is good because of how flexible it is and cognac brown not only looks more expensive but goes with most outfits.
- Consider what boots might be the most versatile for you, in terms of color. Black, of course, is always good, although you want to be careful with it. Black thigh-highs can be pretty intense and so aren't the best choices for work.
- One of the ways to pick the color for your boots is to match it to a shade of color on your head. Fashion advisers say that this make it so the eye travels the full length of your body, drawing attention back up from your boots to your hair again. So for example, if you have golden-blond hair you might choose boots with a golden sheen. If you have black hair, you would go for black boots.^{[4]XResearch source}
- You can also pick colors that match with your outfits. If you have a tendency to wear a lot of earth-toned outfits you would be better suited to wear brown or earth-toned boots (like olive green).
5
Rock tall boots year-round. Tall boots tend to be relegated to fall and winter fashion. However, you can wear these fashions all year long. A cowboy boot is perfect with the right summer dress, for instance. Or your black Gothic boots perfect even in the middle of summer.
- Tall boots in the summer and spring are best saved for a night out on the town. They give a little bit of class and style and can draw the eye, because most people will be wearing sandals or heels.
- A fun spring look is a pair of tall boots (like knee-high black boots) with a light, floaty spring dress. The two opposing fashion choices balance one another out.
Advertisement

Expert Q&A

Search

Add New Question

Question
What can I wear with high boots?
Veronica Tharmalingam
Professional Stylist
Veronica Tharmalingam is a Personal Stylist who runs her fashion consulting business, SOS Fashion, in Los Angeles, California and Paris, France. She has over 10 years of experience crafting stylish wardrobes for men and women. Veronica is also a professional model and has worked with international brands like Harrods, LVMH, and L'Oreal.
Veronica Tharmalingam
Professional Stylist
Expert Answer
Wear bottoms that don't cover up or extend past your boots. Shorts or miniskirts work really well for this.
Thanks! We're glad this was helpful.
Thank you for your feedback.
If How.com.vn has helped you, please consider a small contribution to support us in helping more readers like you. We’re committed to providing the world with free how-to resources, and even $1 helps us in our mission.Support How.com.vn
Yes No
Not Helpful 1 Helpful 1
Question
How do I wear thigh-high boots without looking trashy?
Veronica Tharmalingam
Professional Stylist
Veronica Tharmalingam is a Personal Stylist who runs her fashion consulting business, SOS Fashion, in Los Angeles, California and Paris, France. She has over 10 years of experience crafting stylish wardrobes for men and women. Veronica is also a professional model and has worked with international brands like Harrods, LVMH, and L'Oreal.
Veronica Tharmalingam
Professional Stylist
Expert Answer
Pair your boots with a modest top that isn't too revealing. You could go for a full-sleeved shirt or a turtleneck.
Thanks! We're glad this was helpful.
Thank you for your feedback.
If How.com.vn has helped you, please consider a small contribution to support us in helping more readers like you. We’re committed to providing the world with free how-to resources, and even $1 helps us in our mission.Support How.com.vn
Yes No
Not Helpful 0 Helpful 1
Question
I am 38, am I to old for knee-high boots?
Community Answer
No. Knee-high boots are a fashion statement that can be made well into middle age.
Thanks! We're glad this was helpful.
Thank you for your feedback.
If How.com.vn has helped you, please consider a small contribution to support us in helping more readers like you. We’re committed to providing the world with free how-to resources, and even $1 helps us in our mission.Support How.com.vn
Yes No
Not Helpful 2 Helpful 14

See more answers

Ask a Question

200 characters left

Include your email address to get a message when this question is answered.

Submit

Tips

Shop for boots at the end of a long day. Your feet will be a little more swollen at this point, but this will allow you to get an accurate idea of how the boots will feel after spending a day in them.
Thanks
Helpful0 Not Helpful0
A fun fall look is to layer socks over your jeans or leggings so that they show up over the tops of your boots.
Thanks
Helpful0 Not Helpful0
Balance out your accessories by drawing attention to your neck or face. Bold earrings, a bright necklace, or a colorful scarf around your neck may add enough detail to the top of your outfit to prevent your appearance from getting too bottom-heavy.
Thanks
Helpful0 Not Helpful0

Show More Tips

Warnings

Remember, if you wear your boots to work, choose a fitted boot that has no studs, zippers, or other decorative elements.
Thanks
Helpful19 Not Helpful10