Wednesday, December 6, 2023

Ankle Boots To Wear With Dresses

What About The Popular Wedge Heel Ankle Boot

How to Wear Ankle Boots with Dresses

While this has to be one of the most popular and fashionable styles of ankle boots, its not the most versatile or practical, but when worn with aplomb, they can create an incredibly stylish statement outfit. Wedge ankle boots will go great with a pair of black leggings, or skinny jeans tucked in so that you can show off the full design of the boot. Theyre also super cute worn in the winter with thick black tights and an oversized jumper dress for a very chic yet casual daytime look.

Louise Et Cie Jadran Pointed Toe Bootie

Trying to match ankle boots with a dress that leans more towards the formal side? These elegant booties from Louise Et Cie are perfect. The unique combination of suede and smooth leather makes these more than just another pair of black booties. A pointed toe and sculptural heel give the boots a sophistication that could easily go with a midi skirt or a dress that hits above the ankle. Whether you’re dressing up for a fancy dinner or an important presentation at work, these boots will have you striding with confidence.

Pair A Sweater Dress With Black Ankle Boots

Black ankle boots are a versatile choice for pairing with a sweater dress. Not only do they add some subtle color to the look, but they can also be worn with many different types of outfits. The key is to ensure that your boot choice works well with your body type. If you have shorter legs, try on shorter boots if you have long legs, go for longer boots.

If youre looking to dress down an outfit or add some warmth in colder months, black ankle boots make a great option because they wont clash with neutral colors like gray and browns . Theyll also help anchor an otherwise casual look like jeans and a button-down shirt by adding structure to it through their structured shape and height compared to sneakers or flats.

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How To Wear Booties With Work Wear

When I asked yall to send in your questions regarding booties, I got quite a few regarding how to style booties in a way that still looked appropriate for work. After thinking it over, I decided the best way to cover such a broad topic was to pick a few popular/common work silhouettes and then discuss the booties that look best with each.

As a general rule, Id suggest pairing your work outfits with nicer-looking booties. Usually the material and the shape and style are what make a boot look nicer. In my experience, I think a pointed-toe leather bootie works best for work. But again, it truly depends on your work environment and the weather too!

I chose two popular pants to style for you to give you a visual of what I think looks best.

black bootie

I think booties look great with a wide-leg gaucho pant. My main tip for styling here would be to just make sure the ankle of the bootie goes up far enough so that you arent showing any skin it looks more professional that way. Also, I think a pointed-toe bootie looks more flattering in this circumstance and dresses up the look for work. What do yall think?

white booties

Maybe even more popular than the gaucho pant is your everyday skinny pixie pant. I used to wear my J.Crew ones almost every day for work, so I thought it would be a good option to style. I tried on a few different bootie options with these pants and I think my main takeaways are the following:

How To Wear Ankle Booties With A Skirt


If youre ready to swap in separates for a dress, try your ankle booties with a skirt. Bring your booties to work with a pencil skirt and a pair of stiletto ankle booties, then add a polished button-up. Take your booties and skirt combo into the weekend with a pair of stacked heel booties and a flowing midi skirt.

Stylist Tip: If its too chilly try a pair of tights that match your ankle boots for a streamlined and chic look.


Now that you know how to wear ankle booties with a dress, are you ready to add this style staple to your collection of closet essentials? Take your style quiz, order a Fix and let your stylist know what you are looking for. Try on your five curated pieces at home, keep what you like and return the rest. Its as simple as that. Shipping, returns and exchanges are always free.

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Option 3 With Long Jeans: Tuck Your Jeans Into Your Booties

There are no hard and fast rules for tucking jeans into a bootie. It truly depends on the jean and bootie combo. I try to avoid the bulky look though, so when Im tucking jeans in I usually tuck a super skinny jean or legging into a wider shaft bootie.

In this look above, you can see that the booties have a wider shaft opening. In this case, I think a super skinny jean looks really great tucked in because theres room for the jean to breathe a bit.

Leopard booties

It also works great to tuck skinny jeans into booties with a higher shaft that have a wider opening like these booties above. Its kind of hard to tell in the photo, but the shaft of this bootie is not tight around my leg so theres room for the jeans to be tucked in without them bunching up!

And the same goes with faux leather leggings like in this look above! Because the leggings are tight to my leg, they look nice when tucked into a bootie regardless of how high the shaft is.

Wear A Long Sweater Dress With Ankle Boots

A long sweater dress is an easy way to look pulled together without having to wear pants. It also gives you the comfort of an oversized shirt, but looks much more professional than that can sometimes. And, of course, you can pair it with all sorts of accessories: scarves, hats, beltsthe list goes on!

This trend works well all year roundin spring and summer when temperatures are warmer and in fall and winter when the weather gets colder. I love pairing my sweater dress with ankle boots because they add some height and keep my legs warm during cooler months since they cover most of them up!

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Sorel Womens Joan Of Arctic Wedge Boots

This is a wedge shoe that women can wear with skirts or dresses. It has zipper detail and waterproof full grain leather. This wedge boot is super comfortable and you can wear it all day. Irrespective of the weather, you are good to go.

This boot is retailed for about Bottom of Form

$164.99 as of the writing of this article. But you can look the current price with link below.

How To Wear Ankle Boots With Sweater Dresses

How to Wear Ankle Boots With Dresses

Ankle boots look good with mini to maxi sweater dresses that are either boxy or tight.

With mini sweater dresses, wear leggings that match your dress or shoes, or you can wear hose or leggings. If it’s not too cold, you can wear socks that pop out above your boots.

I love speckled socks, myself for fall, but thin, dainty socks will also add some nuanced appeal!

Maxi sweater dresses also look great with flat ankle boots for a casual outfit. Make sure there is enough space between the boot top and the dress’ hem so that it doesn’t get caught on the boots as you walk.

That’s why lower ankle boots are better. However, you can bypass this rule by wearing a wide sweater dress style with a front or side slit.

Want to elevate your look? Pair your sweater dress with tight ankle boots like stiletto satin sock booties, and add a small metallic purse to make a statement! Learn how to wear sweater dresses with boots, here.

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Isabel Marant Metallic Pink Ankle Boots

Pink is the color of passion and, when paired with metallic accents, it could make anyone happy within seconds. These metallic pink ankle boots are just the perfect answer to the pink and metallic trend that is making everyone run amok both on the runways and down the streets, and will surely give you the needed extra-factor whenever you are in the mood to dress to impress . You can find them at Farfetch.

How About Styling Up The Stiletto Heel Ankle Boot

Automatically adding more va va voom to an outfit and elevating your look to a whole new sophisticated level, the stiletto ankle boot never fails to look sensational and to deliver an upscale vibe. Best worn at night for when you want to make an entrance or know that you wont have too much standing around to do!

A gorgeous dressy stiletto ankle bootie will go with a sharply tailored and tapered trouser suit, a pair of leather trousers or with a little black cocktail dress. This style of ankle boot will deliver a polished finish to a daytime look or bring real drama and elegance to your dressier nighttime styles.

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A Final Thought About Womens Flat Heel Ankle Boots

No heel or flat ankle boots can be more challenging to carry off, especially if you happen to be on the more petite side. You definitely wouldnt want to pair these kinds of shoes with anything dressy or glamorous.

The flat is best worn in the summer with shorts, in the spring with a swing dress and the winter with your jeans. This type of boot is also loved by the Boho self-styled girl who loves a long floating maxi style dress with a pair of strategic flats for a very casual but still chic vibe.

Last Updated on December 19, 2021 by admin_comfortabledressshoes

How To Wear Ankle Boots To Work

How To Wear Ankle Boots and Booties With a Dress: 10 Chic Ways

In true versatile style, ankle boots can be dressed up as well as down! You can pop on a pair for work, before continuing the evening at a fancy restaurant without having to switch your shoes. The key for super formal events is to choose a smart pair of leather ankle boots and ensure they are well-cleaned and polished.

Ankle boots with pointed toes and slender heels are a fabulously sophisticated choice. Pair your ankle boots with a smart dress or suit for work, or for evening events wear them with a smart trouser and blouse combo.

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Pointed Black Ankle Boots Match Every Dress

If you want to invest in only one pair of boots, it has to be a pair of pointy black ankle boots.

These boots are the supporting act to your outfit, allowing your dress to take center stage if you chose a solid jewel tone color or animal print.

Chloe Paige, Sophie Porley, and Paris Hilton in animal-print dresses with pointed-toe ankle boots

If you are looking for a more minimalistic outfit, then nothing beats a pair of black ankle boots. These shoes can be paired with midi-dresses for formal events or mini dresses for a girls night out.

Throwing on a black dress with black tights, cute booties, a great coat and throw a scarf over it. I think simple accessories and, if you want to make a pop, a great red lip Meghan Markle

This style of shoes is a staple in the closet of legendary Vogue Editor in Chief Anna Wintour, who is one of the biggest advocates for wearing ankle boots with a dress.

Alexa Chung, Karen Gillan, and Nicole Scherzinger wear dresses with black pointy ankle boots

How To Wear Booties With Dresses And Skirts

In my personal experience, there arent any strict rules for wearing booties with dresses and skirts. I feel like most booties work with all sorts of dresses and skirts and that it truly just depends on your personal sense of style and preference.

However, I will say that my favorite bootie to wear with dresses and skirts is a tall shaft with a pointed toe. This elongates my legs and the entire look! With that said, rounded toes and shorter shafts also look great. So wear whatever makes you feel most comfortable!

I hope these looks made my point that I think all booties pretty much work when youre pairing them with any sort of dress or skirt!

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How To Wear Ankle Boots With Jeans

Wearing ankle boots with jeans is a great way to ease into the bootie trend if you’re just not sure what to pair them with. Whether you are dressing your jeans up or down, there are different types of ankle boots you can wear to stylishly assist in the process.

Cropped jeans and ankle boots are a match made in heaven. Cuff the hemsinstead of tucking them into the bootsfor some major ankle action. The cropped hemline creates a frame for showing off your favorite booties. If you’re going for a really casual look, wear brown ankle boots with cuffed jeans for a relaxed vibe. If you want to add an extra element of style to your denim outfit, make sure your booties have a pop of color. Finally, pair the look with an oversized sweater for a casual fall ensemble that still looks polished.

How Should Your Boots Fit Around Your 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. There should be enough space for one finger to easily fit in there, but any more than that and the boots might be a little on the loose side! If you cant even manage to squeeze one finger between your ankle and your boot, then they might be a bit too tight.

Its worth trying on your shoes before you make a purchase, or why not make the most of our in-store fitting service to find your perfect fit and style?

From Chelsea boots and walking boots to chunky-soled styles and pointed heels, theres an ankle boot for every style, preference and occasion. For more style tips and advice, take a look at our guide to knee high boots, or discover how to rock a pair of biker boots.

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Chelsea Boots With Dresses

Chelsea boots are a great type of boot to wear with dresses. They add a touch of edge and style to any dress, whether it is a maxi, mini, slip, or sweater dress. Plus, they are comfortable, which is an added bonus!

Chelsea boots are mostly just over the ankle, but you can find many that are almost knee high. Trendy Chelsea boots come with an elevated platform, making them an extra rugged look.

These boots can be easily dressed up with a silky dress and blazer or dressed down with a sweatshirt dress, a moto jacket, and a crossbody purse.

You can’t go wrong with wearing a pair of brown or black Blundstones with a dress for a classic, everyday look. I love these with a floral sundress, tights, and a slick leather jacket.

There are many great ways to wear Chelsea boots with dresses and other outfits. Check out my post all about how to wear Chelsea boots for more!

Best Dresses to Wear with Chelsea Boots:

Silver Shoes & Metallic Hues

When worn with metallic shoes like silver or even metallic gray, black looks stunning. The greatest part about silver is that it will bring your ensemble a lot of pizazz and flair, which is why silver shoes are almost always featured in style guidelines like these. Put on a pair of silver ballerina flats with your little black dress for a relaxed appearance. When attending a night party, switch it up with a striking pair of stiletto heels, and youre good to go!

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What About When Your Skinny Jeans Are Long

In other words, when your jeans are not cropped.

Usually, when we buy jeans, we buy them to fit the length of our legs. They look great with normal flats or sneakers, but when you try and wear normal-length jeans with booties, you have an issue. Meaning your jeans and bootie overlap with the shaft of the bootie going up your ankle and running into the bottom hem of your booties. This overlap can look pretty messy and bunched up, which is why it has become so popular to ROLL your jeans up.

So, with that said, Ill show you the different ways you can wear your jeans with booties when your jeans are FULL length.

When youre wearing full-length jeans with booties, you have three style options:

  • Roll up your jeans
  • white booties

    First, I do want to mention that Ive found showing a little skin by either rolling up or under my jeans elongates my legs. Note how in the photo above I have one leg tucked in and one rolled up. I think they BOTH look great but for some reason rolling up my jeans always makes me feel better and I think its oftentimes more flattering. I realize this isnt always possible though when its super cold outside. OK, moving on!

    Now lets discuss when to roll up vs roll under vs tuck in your jeans!

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