How To Wear Socks With Ankle Boots & Booties

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Ankle booties – including cutout boots – are the perfect go-to footwear for any season. Whether you’re looking for a touch of fashion or practicality, booties are the perfect choice for all occasions.

But, what kind of socks should you wear with boots? In this article, we’ll discuss all the types of ankle boots and booties, the different types of socks you can (and should) wear with them, and the best way to style them including outfit ideas.

The most important thing to remember is that ultimately the socks you choose to wear with your short boots will depend on your personal style and the look you are trying to achieve.

Ankle Boots vs Booties

While the terms ankle boots and ankle booties are often used interchangeably, there is a subtle difference!

Ankle boots are typically slightly taller boots with a higher shaft than booties and come in classic styles like Chelsea boots, while booties often offer a more casual look as they are low-cut shoes that you would wear with jeans or a skirt.

Both styles of boots can come in a variety of materials such as leather, suede, and fabric. They also come in countless styles and may include cutouts, a pointed toe, gold hardware, and even a stiletto heel.

Either one of these boots is not only a great option for cooler weather but they make a great stylish addition to any outfit in warmer months as well!

Different Styles of Boots

Cutout Boots

Cutout booties are a style of boot that features cutouts around the ankle, heel, and/or toe area. These boots come in a variety of different styles and materials, from pointed-toe to tall boots, and from leather to velvet material.

Cutout booties are perfect for elevating any outfit making them a great versatile and fashionable option for dressier occasions.

Chelsea Boots

Chelsea boots are a classic and timeless type of ankle boot that features a low heel, a rounded toe, and the signature elastic side panel. They are characterized by their sleek and simple design and are most often made from leather.

These boots are popular among men and women and are versatile enough to be worn with both casual and formal attire.

Combat Boots

While originally created for soldiers in combat or trudging through rough terrain, combat boots became a fashion staple during the late 20th century. They are identified as large black boots made up of leather with lug soles.

These boots are best worn with taller socks, particularly wool socks, as they will prevent rubbing against the calf muscles and will help to keep your feet dry.

Tall Boots

These boots are generally classified as any boots that extend above the ankle, this can include knee-high boots or thigh-high boots, riding boots, or even combat boots. They can come in a variety of different styles and materials.

Tall boots are best worn with tall socks that extend nearly to the top of the boot if not over the top of the boot.

Knee Boots

Knee boots are a type of tall boot that extends above the calf, reaching the knee. The difference between them and over-the-knee boots is that knee boots do not extend above the knee.

These are worn for both fashion and aesthetic purposes and pair well with everything from skinny jeans and sweaters to formal outfits.

A woman wearing black ankle booties

Do you wear socks with cut-out booties?

Cut-out booties are a fashion-forward and stylish alternative to traditional ankle boots and can add a unique and edgy touch to any outfit, but the answer to the question “do you wear socks with cut-out booties?” is simply – it depends! It depends on the style of the cut-out booties as well as personal preference.

Some people prefer to wear cozy socks with cut-out booties for added warmth and comfort, while others prefer to show off their ankles and legs. This will obviously depend on the weather as well.

If you do choose to wear short socks with cut-out booties when the style allows, it is best to opt for a low-cut sock (or no-show socks) that won’t peek out above the cut-out “V” or the top of the boots. You will also want to consider the color of socks and boots as well.

If you’re wearing white ankle boots or cut-out booties you’ll want to choose neutral-colored socks that match well with the boots.

Ultimately, whether or not you wear socks with cut-out booties is up to you and what you feel most comfortable and confident wearing.

Can you wear socks with open-toed shoes?

While you can wear socks with open-toes shoes, it is definitely a more difficult look to pull off. For most people, this look will require coming out of their comfort zone.

Typically, socks are not worn with open-toed boots or shoes because the purpose of the toe cutout is of course to show the toes.

However, if the weather or occasion permits, wearing a solid color sock with open-toed shoes might be an option. You should of course take the rest of the outfit into account and consider the look and style you’re going for.

If you’re unsure whether or not to wear socks – when it comes to open-toed shoes it’s best to err on the side of caution and ditch the socks for a bare-foot, open-toed look!

A woman wearing black ankle boots with no show socks

Should you wear socks with ankle booties?

Yes! The great thing about ankle booties is that your socks are concealed. It is generally appropriate (and recommended) to wear socks with ankle boots or booties for several reasons.

For starters, wearing socks with ankle boots provides added warmth and comfort to your footwear which can be especially important during cooler or winter months!

Second, wearing socks with any type of closed-toed shoes is recommended for hygiene purposes! Wearing boots with bare feet increases the risk of foot conditions and infections such as athlete’s feet.

Not to mention the higher risk of developing painful blisters due to the friction caused by bare feet rubbing against the material on the inside of the boots.

Lastly, wearing socks with booties can add a lot to your overall look and outfit! If you’re opting to show the socks by choosing higher socks that go above the boot, assuming it’s cohesive and intentional, it can create an aesthetic and stylish look!

The Best Socks To Wear With Booties & Ankle Boots

Ankle Socks

These low-cut socks extend only as high as the ankle and are a good option for many different styles of booties and ankle boots. While they come in numerous materials, cotton is a lightweight material that’s great for all seasons!

No-Show Socks

These types of socks are the most popular for cutout booties as they are designed to stay hidden within the shoe. They are also known as foot liners or liner socks and are not visible above the shoe’s top line.

No-show socks are also typically worn to prevent foot odor by keeping the feet dry and to prevent blisters and chafing.

Crew Socks

Crew socks extend above the ankle and up to the calf and come in a variety of materials like cotton, wool, and even spandex blends.

They are a great option to wear with booties and ankle boots as an everyday sock – even if they extend above the top of the boot, it’s very stylish to bunch them at the top of the boot.

Wool Socks

Socks made of wool material – particularly merino wool – are great options for wearing with boots as they are a moisture-wicking material that helps to keep the feet dry as well as warm.

However, while they’re great for cooler weather, they may be too warm in warmer weather in which case it’s a good idea to opt for a cotton style.

Alternatively, socks made of bamboo fiber are another great option for both winter and summer as it helps to regulate body temperature.

Knee Socks

Tall socks like knee-high socks are simply socks that extend to the knee. They come in a variety of different colors, textures, and materials and can offer a fun look when worn with the right boots!

Trouser Socks

Trouser socks also known as dress socks or pantyhose have traditionally been worn with trousers or dress pants. They are made of lightweight materials such as nylon and polyester and were designed to be invisible.

However today, trouser socks come in fun patterns and can make a great addition to a stylish outfit.

Styling Tips for Socks with Booties

When styling socks for ankle boots or cutout booties, there are a few things to keep in mind:

  • Choose the right socks

Opt for thin, low-cut socks to avoid bunching and to keep the look sleek. If you are going for a look with visible socks, ensure they go well with the rest of the outfit!

  • Keep the color neutral

Stick to neutral colors such as black, gray, or nude to match the boots. A bright color will be harder to conceal.

  • Be mindful of the length

A general rule of thumb is to make sure your socks don’t peek out above the top of the boots or bunch around the ankles unless, of course, this is the look you’re going for!

  • Consider the weather

Opt for a thicker, wool sock in colder weather for added warmth. When wearing cutout booties in warmer months, you may opt for thinner, shorter socks or no socks at all.

  • Experiment with texture

Mix up the texture of your socks and boots to add visual interest when wearing socks that will extend above the top of the boots.

  • Pair it with the right outfit

Ankle booties can be paired with a variety of outfits, from skinny jeans to dresses. Ultimately, the most important thing is to choose boots or booties with a pair of socks that complement the rest of your outfit.

Outfit Ideas To Wear With Booties

There are so many different options and stylish ways to put together outfits with boots and booties. Here are a few simple looks you can recreate with items you probably have in your closet already.

Skinny Jeans

A pair of ankle boots and skinny jeans is a popular fashion trend that can be worn in both casual and dressier settings. The combination of the slim-fitting jeans and the snug fit of the booties creates a sleek, more polished look.

Leather Jacket

Pairing booties and a leather jacket is a classic and edgy look that is great for any occasion. With a leather jacket and pair of booties, you can make countless stylish casual outfits or pair them with a dress for a more formal look!

Straight Leg Jeans

Straight-leg and wide-leg pants are very trendy right now and pairing them with ankle boots or booties makes a great outfit option. The versatility of straight jeans allows them to be dressed up or down and you can easily add a pop of color with a vibrant sweater or blouse.

Midi Dress Or Midi Skirt

Short boots are a great compliment to midi skirts, especially for those with short legs! Ankle boots are just the right height to pair with a midi dress or skirt to show just a bit of skin and are a great look no matter the weather.

Black Tights

Black tights and black booties make a chic and stylish combo, especially for the cold weather. This pairing works perfectly for everything from an afternoon of lunch and shopping to a more formal work event. This is an easy and classic look to pull off by pairing it with a dress or cozy sweater.

For a fun way to easily change up this look, choose a pair of tights in a patterned style.

Little Black Dress

Booties make a beautiful addition to all sorts of dresses. A little black dress is a classic staple that can be dressed up or down depending on the boots you choose. You can never go wrong with a black dress and a pair of cutout ankle boots!

Cropped Pants

Cropped pants with a shorter hem are a great way to show off your boots and possibly a little skin. This combination of clothing is relaxed yet still gives you a polished appearance!

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