Tall boots can look chic and attractive when worn correctly. 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.
Showcasing Your Boots
Show off your thigh-high boots. These boots, because they are dramatically tall, will be a focal point of an outfit. They are sexy, while still being entirely modest! They will bring attention to your legs, in a feminine and tasteful way. 
If you want to tone down the boots a little (for example, if you’re wearing them to work) simply overlap the skirt of your dress with your boots about one inch (or three centimeters).
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 people’s attention will be drawn down to your legs, your leggings, and your boots.
You can also 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). While still showing off your legs the attention will be on your boots.
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 loose or flared jean cuts, such as “boot flare” or wide pant legs. These may bunch up if tucked into your boots.
Pair your boots with a miniskirt. There’s nothing better for showing off legs and tall boots than a nice little mini-skirt. 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. This is not a look, however, that you particularly want to wear to work, or on a family outing.
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.
Glam up your weekend boots. If you want your boots to be the focal point of your outfit, especially if you’re going out with them, then you’ll want to choose ones that are exciting and draw the eye. It’s best not to try and incorporate a bunch of glam into one pair of boots. For example: crimson stiletto-heeled boots with lots of metallic chains is going overboard. 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 (although you might want to avoid trying to look like a flower child from the ’70s).
Incorporating Boots into Your Outfits
Use knee-high boots for work. There are certain boots that are great for fitting into your wardrobe. They don’t draw too much attention, but instead give you a little quiet boost in the fashion department. Knee-high boots are great for incorporating into outfits without taking them over. 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 tailoredshirt. Through on a cardigan for the cooler months.
Temper the over-the-knee style. The over-the-knee boot can be great for showing off your legs, but you can also temper it with certain fabrics and outfits so that it doesn’t take over what you’re wearing.
Go for soft colors like various shades of brown in the boot. Also, you want to pick soft fabrics like a soft suede. This allows the boot to seem more casual.
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.
Wear riding boots. There are two different types of riding boots: cowboy boots, and the regular riding boots. Both types can help foster a great casual look for your outfit, without drawing too much attention. Riding boots look best with sleek lines (like skinny jeans or leggings). 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 toningdown a really feminine dress. They can help balance out a really frilly or flowery dress, an especially good look for spring.
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 doesn’t really work with jeans is the thigh-high. Thigh-high boots tend to go best with short skirts or leggings.
Choosing the Right Boots
Avoid gaping. 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.
Avoid boots that land at the thickest part of your leg. 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.
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.
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.
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).
Rock tall boots year-round. Unless it’s really hot, there’s no reason that you can’t wear boots all year round! Of course, some tall boots (like rain boots) can be more useful and necessary than others, but that’s not the only reason to wear boots.
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.
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.
A fun fall look is to layer socks over your jeans or leggings so that they show up over the tops of your boots.
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.
Black leather and suede have a classier feeling to them and may help you dress an outfit up.
Remember, if you wear your boots to work, choose a fitted boot that has no studs, zippers, or other decorative elements.
Sources and Citations
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