How to wear ankle boots with tights? (2024)

Dear VienneMilano,
I recently purchased a cute pair of ankle boots. While I love the style, I'm not sure what to pair the boots with. How can I incorporate ankle boots with stockings for work?

Briana C.

Thigh boots, cowboy boots, or ankle boots - boots are generally a fabulous complement to hosiery. To start, the three things to consider when pairing boots and tights are:

  • The Occasion – Typically, boots are not appropriate for formal occasions (with exceptions, of course). Instead, boots are ideal for work, parties, hanging out with friends, and night out in town.
  • The weather – What's the temperature outside? For warm summer days, give fishnet stockings and ankle boots a try. For cold winter days, try pairing thick stockings (55 deniers and up) with your boots.
  • The Outfit – Dresses, skirts, and pants are all fashionable items that can be paired with hosiery and ankle boots. For cold winter days, thigh highs can be worn underneath your pants for warmth.

The Do's and Don'ts of wearing ankle boots with stockings:

DO's:

  • Do wear ankle boots that match the color of your stockings - otherwise, your outfit may get a bit overwhelming.
  • Do wear fishnet stockings with ankle boots - Rock this classic look fiercely.
  • Do wear pattern stockings with ankle boots - Kick your outfit up a notch by mixing pattern tights with boots.
  • Do wear boots and hosiery during cold weather - stay warm by wearing thick tights underneath your dress or skirt.

DON'Ts:

  • Don't wear ankle boots and hosiery of two different colors - Let's be honest, that's a lot going on!
  • Don't wear boots and stockings to formal occasions (unless you're going to a cowboy-themed wedding or some other exception); we recommend keeping boots at home for co*cktail parties, weddings, horse racing events, and funerals.
  • Don't wear over-the-knee socks with ankle boots and a skirt. Over-the-knee-socks tend to emphasize on the exposed part of your thigh that sits between your skirt (or dress) and the top of your socks which can make your legs look short. Instead, wear thigh highs that reach the top of your thighs so that your legs will look even more fabulous!

To illustrate our recommendations, here are a few looks.

How to wear ankle boots with tights? (1)
How to wear ankle boots with tights? (2)
How to wear ankle boots with tights? (3)

At VienneMilano, we always believe that legs are a canvas for color and texture, and hosiery allows you to express your creativity. Ankle boots and stockings are a fabulous complement. How do you wear your boots with stockings? Leave us a comment below.

February 14, 2020

How to wear ankle boots with tights? (2024)

FAQs

Can I wear ankle boots with tights? ›

Do wear pattern stockings with ankle boots - Kick your outfit up a notch by mixing pattern tights with boots. Do wear boots and hosiery during cold weather - stay warm by wearing thick tights underneath your dress or skirt.

Should you wear tights with booties? ›

The combination of tights and boots is one of the most versatile outfit options you can have in your wardrobe. Tights and boots pair together for work, for travel and even for a fun night out.

What not to wear with tights? ›

A shimmering top, a fancy blouse, or a baby doll dress simply don't go well with a stretchy, tight pair of leggings. Resist the temptation to be too adventurous with your style, as leggings are not sophisticated enough for dinner dates or other more formal events.

How to wear ankle boots 2023? ›

TLDR: You can wear ankle boots with skinny jeans that are tucked in, rolled under or with a pair of jeans that hits at the ankle. The same rule applies for straight-leg jeans. If your booties are short, don't tuck them in. If your booties are tall, they'll look best with tucked-in skinny jeans.

How do you wear booties over 50? ›

roll up and leave 1/2″ of ankle between the boot and your pant. You can fold over twice to have a narrow cuff or one large fold. Be aware, the wider the cuff, the shorter your legs will look. If you cuff your jeans, wear a shorter top to help elongate the look of your legs.

Can you wear tights with open toe booties? ›

So, yes, you can wear hosiery with open toed shoes – but only if you choose an appropriate style of footwear, and a certain type of hosiery. Sounds like a complicated fashion formula, but getting this look right doesn't require a degree.

Is there a right way to wear tights? ›

While sitting, hold your tights at the waist and gently gather each leg with your thumbs until you're at the toe of your tights. Next, gently slide your foot into the tights one foot at a time. Pull your tights up, while still keeping your thumbs inside to avoid snagging.

Should ankle boots be tight or loose around ankle? ›

Different styles of ankle boot will have a slightly different fit, but generally, your boots should fit nice and snug around your ankles without feeling too tight or too loose. One way to tell if your boots fit properly is to pop a finger between the back of your ankle and your boot.

Are ankle boots in style 2023? ›

Timeless and versatile, the best ankle boots of 2023 are absolute wardrobe essentials. Chelsea boots, platforms, kitten heels — whatever your preference, these tried-and-true staples are endlessly versatile. So finding a pair you can dress down with classic denim or up with playful dresses is not difficult...

What kind of pants go best with ankle boots? ›

Cuffing jeans works best with ankle boots, because the cuff will fall right at the top of your boots. You can cuff straight-leg jeans and boot-cut jeans. Alternatively, you can also wear ankle jeans or cropped jeans with ankle boots—the jeans will naturally fall at your ankles so you will not need to cuff them.

Do pants go over or under booties? ›

With wider leg openings, it's not about cuffing or the hem grazing the top of your booties. These jeans are normally worn longer, so the most comfortable way to wear them is when the shaft of the bootie goes up under the leg of the jeans.

What time of year should you stop wearing boots? ›

Boots are a great year-round staple, keeping you warm and stylish in the Winter while easily transitioning into a must-have Spring accessory for the chic, cowgirl or not. Boots give us that extra pep in our step for the warmer months, from pairing them with dresses, skirts, shorts, denim jumpsuits or jeans.

Should booties be tight or loose? ›

Boots should not be too loose or too tight on your foot. The best fit should be snug (but not tight) around the whole of your foot, with enough room to move your toes and a maximum of a quarter to a half-inch of slippage at the heel.

Are tights in style 2023? ›

After numerous trend cycles of bare legs being a major theme on the runways, hosiery is returning to the spotlight—and in all forms. From tights and stockings to socks (of all heights) and even stocking-like things, hosiery has become a big part of 2023's trend conversation.

When should I start wearing black tights? ›

Black tights are best worn in the transitional months like fall and early spring, and of course, they save any winter wardrobe. However, because of the heat, you will probably avoid them in the summer months. Black tights can be worn in casual daytime events and evening events.

Can you wear black tights with everything? ›

You can wear black opaque tights with anything.

We all know that black is a neutral color and can be paired with anything.

What length pants to wear with ankle boots? ›

Your straight leg or skinny pants and jeans that end several centimetres above the top of your ankle boots are an ideal pairing. There's no need to make that space with a cuff or roll because it is already there.

Do jeans go in or over ankle boots? ›

Skinny jeans should be worn inside your ankle boots. All other styles of denim like straight leg or flare should be worn outside your booties. Either look for a pair that is cropped and hits above the boots, or do a messy cuff that rests on the top of your booties.

What boots are in style for fall 2023? ›

In 2023, sleek, heeled, black leather boots will be the most popular shoe on everyone's feet. The key to this trend is wearability—the heel height itself shouldn't be very high at all! Instead, look for a boot with a kitten heel height. This style looks amazing with long dresses and skirts.

How do you wear fashionably ankle boots? ›

They go with jeans, dresses, skirts (both minis and maxis) and help to elevate any look where you may have just thrown a sneaker on. They're super versatile in that you can wear booties with casual looks like jeans and tees, but can also be dressy enough to pair with a dress for the office or a date night.

How do I not dress frumpy at 50? ›

How Not To Look Frumpy Over 50
  1. Bold, Bright Colors. A great way to avoid feeling bored by your clothes as you get older is to keep things fun! ...
  2. Fun, Funky Patterns. ...
  3. Experiment With Silhouettes. ...
  4. Spice Any Outfit Up With Accessories and Handbags. ...
  5. Take It to the Next Level With Shoes. ...
  6. Related Articles.

Is it OK to wear socks with booties? ›

But most booties can accommodate socks, and it's fine if they show, as long as they work with the rest of the outfit. In fact, sometimes they add another element of interest that can really make the look.

Is it OK to wear socks with ankle boots? ›

As a general rule of thumb, taller boots work best with knee or over-the-knee socks, while shorter styles (think trouser or crew socks) pair well with ankle boots or booties.

Is it fashionable to wear socks with ankle boots? ›

It's best to avoid wearing them sans socks, as to keep them smelling their very best, for as long as possible (and, of course, to prevent freezing your feet off when the temps drop). As it turns out, though, pairing ankle boots with socks can actually look very stylish, and fashion girls have nailed the combo to a T.

What makes tights attractive? ›

Tights show your curves much better than anything else apart from perhaps a waist cincher or corset under your dress. They're often figure-forming if you go for compression tights, but even if they are not then the way they draw your gaze means that your curves are easier to show off.

Should you size up or down in tights? ›

Bigger is better

After consulting the size chart, if you find yourself to be in-between sizes or at the upper end of a size range, you should always opt for the bigger size. Tights are typically made small and considering their close fit, it's better for them to be bigger rather than too small.

How far up should tights go? ›

Ideally, your stocking band should be tucked away underneath your pencil skirt or dress. Wherever your hemline ends, your thigh highs should start (or above that!) The aim is to keep it hidden away even as you walk, strut, dance, etc. In the fashion world, there are no hard-set rules.

How tight should an ankle boot be? ›

We suggest using one under the ankle strap as there is no padding there. Fasten the remaining straps until your foot feels snug but not tight. If you fasten the boot too tight you may cause pressure to your skin. Ensure your heel is positioned right at the back of the boot.

Should I size up or down for ankle boots? ›

Most boots should be purchased a half size smaller than your true size. Check with the company if this is true for them before making your purchase.

What is the point of ankle boots? ›

They transform a midi skirt, or trousers or jeans cropped at the ankle, into an interesting look. The ankle boot has risen as hemlines have fallen. An ankle boot is not particularly flattering, so when skirts were short and leg-lengthening illusions were called for, it didn't really work.

What toe shape is in style 2023? ›

The square toe shoe trend is back in fashion for 2023.

Can I wear ankle boots with a dress? ›

Short boots, like ankle boots and Chelsea boots are perfect for wearing with dresses through every season, whether it be winter or summer. Ankle boots are perhaps the most popular style for wearing with dresses as their short silhouette will elongate the appearance of your leg.

Can you wear ankle boots with short pants? ›

But it turns out cropped trousers can work wonderfully in autumn, and arguably look even better with ankle boots than full-length trousers. Think about it; the higher the hemline, the more boot is visible.

Can you wear ankle boots with wide leg pants? ›

Done right, wide-leg and high-waisted pants can be worn with booties for a beautifully chic look. In most cases, you'll want to try pairing some type of heeled ankle boot with these styles to balance a wider pant.

Can you wear ankle boots with a dress or skirt? ›

Ankle boots can also look incredibly stylish when worn with a dress or a skirt, no matter the length. Whether you're rocking a maxi skirt on the weekend or sporting a midi dress to work, there is an ankle boot that will work with your outfit.

What does it mean when you tuck your pants in your boots? ›

Tucking your jeans into your cowboy boots serves three purposes: First, it prevents your jeans from getting dirty. Second, it gives you better access to the roper boot's kick-off heel if you need to take them off in an emergency.

How are boots supposed to fit with pants? ›

The jeans should be long enough to protect your legs and cover the shaft of the boots, but not so long that they drag in the back or get stuck under your heel. Ideally, they should rest just above the heel of your cowboy boots by a quarter to a half inch.

Where should pants fall on boots? ›

The hem of your pants with a half break should sit ½” to ¾” past the point where your pants first meet your shoes, this will allow a slight horizontal fold to make contact with the front of your shoes.

Can you wear booties in 70 degree weather? ›

Thankfully, 70-degree weather posits a great opportunity to ditch your winter jacket. For those looking for a fashionable (and dramatic) way to say goodbye to snow and slush, an outfit composed of a cream sweater, a corduroy skirt, and a pair of ankle booties will definitely do the trick.

Is it OK to wear the same boots everyday? ›

We define ample time as around 24 hours – so ideally give it a day between wears. If you don't give your shoes a day to air out, the sweat-soaked leather will warp, and your shoes can start to lose their shape — not to mention get musty and start to smell.

Should you wear the same boots every day? ›

When it comes to how often you should wear your favorite pair of footwear, Dan recommends trying to rotate every other day. This not only extends the life of the shoes, but it's best for your feet. “The repetitive stresses of wearing the same shoes day after day, hour after hour, can eventually make us uncomfortable.

Can I wear ankle boots with leggings? ›

Making printed leggings work with ankle boots is tricky business, but it absolutely can be done. Try to stick to classic black or dark brown footwear, to give your funky leggings a solid base. Then, add a textured knit in a complementary color up top.

What is the difference between ankle boots and booties? ›

The main difference between bootie and ankle boots is their height and where the shoe falls on the line of your leg. Booties are shorter in height and should ideally end right at your ankle, while ankle boots will end one to four inches above your ankle, like a Chelsea boot, combat boot, or work boot.

Should you size up in booties? ›

Boots should be the half a size bigger than your shoe size for summer use and should be the same size for winter use. If your feet are wider than average, you will need a larger size to provide more space. Your toes should be from 1 inch to 0.5 inches from the toe cap of the boot.

What clothes can you wear ankle boots with? ›

They go with jeans, dresses, skirts (both minis and maxis) and help to elevate any look where you may have just thrown a sneaker on. They're super versatile in that you can wear booties with casual looks like jeans and tees, but can also be dressy enough to pair with a dress for the office or a date night.

Is it OK to wear ankle boots with a skirt? ›

Ankle boots can also look incredibly stylish when worn with a dress or a skirt, no matter the length. Whether you're rocking a maxi skirt on the weekend or sporting a midi dress to work, there is an ankle boot that will work with your outfit.

Can you wear black tights with white ankle boots? ›

And the plain answer is yes.

You can wear black, white tights and even colored tights with white boots.

How to wear ankle boots over 50? ›

With Skinny Jeans

roll up and leave 1/2″ of ankle between the boot and your pant. You can fold over twice to have a narrow cuff or one large fold. Be aware, the wider the cuff, the shorter your legs will look. If you cuff your jeans, wear a shorter top to help elongate the look of your legs.

Is it fashionable to wear pantyhose with open toe shoes? ›

As previously mentioned, sheer stockings and any type of open-toe shoes do not work. On the other hand, wearing opaque stockings with open-toe shoes is arguably acceptable. Opaque stockings cover your toes which offer a degree of modesty. Matte stockings and peep-toe shoes are the only exceptions to this rule.

Do you wear tights with thigh high boots? ›

Thigh-high boots add a dose of sexiness to all your outfits so it would be a smart idea to avoid all bodycon dresses. Instead, try wearing something oversized, like a sweater or jumper to make a perfect balance. By layering your boots with skinnies, leggings, or tights, you are making space for volumes on top.

Can I wear tights with heels? ›

Heels. If you're stuck on what heels to wear with tights, you're in luck. Any style will complement your outfit, coupled with a cosy addition or two. Paired with leggings and tights, heels can make your bottom half appear long and lean, adding elegance to your look.

What kind of skirt to wear with ankle boots? ›

Try styling a floaty midi dress or skirt with a chunky pair of ankle boots, or pair an elegant co*cktail dress with a more casual leather ankle boot.

Are ankle boots still in fashion? ›

From subtle versions like the Siempre Di Ruched Ankle Boot and the Popa Nude Suede Boot to more traditional ones, western-inspired ankle boots are a perfect long-term investment. They're never out of style and you can wear them with pretty much everything!

What tights to wear with white ankle boots? ›

White boots look best when they "pop", and the color of your skin won't do the trick. I always, always recommend tights by Spanx. Spanx tights are particularly well constructed. And no matter your body type, it's my opinion that everyone could use the smoothing effect of tights constructed with compression.

Is it OK to wear brown ankle boots with black pants? ›

Short answer: yes, you can wear black pants and brown shoes together, but keep a few things in mind. Brown shoes elicit more personality and modern sensibility than standard black shoes but still look professional and appropriate for the workplace.

Do black tights go with anything? ›

You can wear black opaque tights with anything.

We all know that black is a neutral color and can be paired with anything.

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