Tuesday, November 28, 2023

How To Wear Ankle Booties

How Do You Wear Ankle Rain Booties

How to Wear Jeans with Ankle Boots | 15 Cute Boot Outfits!

Pair your wellies with skinny jeans or a frayed mini for a day of laughs. Like skirts but prefer a more polished look? Why not try a slim-fitting sweater, stockings, and a mini skirt for transeasonal appeal. Rain or shine, leave the old sneakers behind and grab your rain boots to get you through the weekend.

What Should I Wear On A Rainy Day

8 Cool Outfit Ideas for Rainy Days Quilted Coat + Jeans + Ankle Boots. Puffer Jacket + Jumpsuit + Leather Boots. Raincoat + Skinny Jeans + Lug Sole Boots. Blanket Coat + Denim Jacket + Turtleneck. Oversized Blazer + Loose Trousers + Sneakers. Leather Jacket + Combat Boots. Trench Coat + Trousers + Chunky Boots.

White Booties + Casual Neutrals

This fall casual look is styled with 90s straight jeans. To balance out the forgiving fit of the shawl, I layered a bodysuit underneath. This is one of my very favorite bodysuits because its thick and not see through, and comes in a ton of colors. I finished the look with a pair of white boots and a Gucci Disco Bag. I did a full review of the bag found HERE.

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Final Thoughts On Styling Ankle Boots With Dresses

There you have it! These are just some ways to wear ankle boots with dresses from spring to fall and even winter.

I do how you’ve left this post feeling more confident about wearing dresses with ankle boots. Of course, as I always say, style is subjective if a particular outfit appeals to you, wear it!

House Of Harlow X Revolve Nick Bo

How to Wear Ankle Boots &  Booties

The beauty of snakeskin booties? They practically are neutral thanks to the blend of black and brown shades and thus go with nearly every outfit. This style’s cool pattern and pointed toe deserve to be shown off, so a cropped pair of pants will do them justice. Feel free to coordinate your top with the neutral shades or simply pair them with a bright color for a funky look.

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How To Wear Ankle Boots 9 Ways

Ankle boots are hands down my most worn shoe come fall and winter. And honestly, also in the springtime. They go with jeans, dresses, skirts and help to elevate any look where you may have just thrown a sneaker on. Theyre super versatile in that you can wear them 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. But I think one of my favorite things about an ankle bootie is that they help in transitioning pieces from summer to fall, or winter to spring.

What Are The Different Types Of Booties

After years of putting together outfits, Ive realized that I definitely need multiple styles of booties to make what I have in my closet work. In other words, one style of bootie doesnt really fit all outfits. And it can be challenging to know which style/color bootie is going to be my winner for the season aka the one I actually wear more than once. Its so frustrating when I think Ive found the cutest bootie ever, I buy it, and then Im only able to wear it like 2-3 times that season. I think we all know how that goes, right?

As you can see, there are SO many different kinds of booties! And I think it helps facilitate the booties conversation to give yall a visual. It just kinda shows what I mean when I say low shaft, tight ankle or mid-shaft, semi-wide ankle, etc. But now that weve gotten that out of the way, we can jump into the different ways to style each type of bootie!

I went back and forth on how to organize all of this whether I wanted to talk about the different characteristics of booties and how to style each of them or whether to start with clothes and talk about which bootie works with each style. Well, let me tell you that I have now re-written this post THREE times and I think the way Ive got it laid out here is the MOST helpful!

I truly hope from the bottom of my heart that this blog post serves your styling needs in some way or another! As always, please dont hesitate to leave comments below and ask questions! Im here to help! 🙂

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Ankle Boots With Black Jeans

Black jeans are up there with little black dresses as a women’s wardrobe staple. With a good pair in your arsenal, you’ll always have something to wear. From happy hour and weekend brunch to running errands and a night on the town, black jeans are a flattering fallback you can rock almost anywhere.

On top, slip into a fitted V-neck with a blazer, an extra-long cardigan over a camisole, a crisp white button-down, or a flowy tunic. We also appreciate that nearly every color goes with blackand most shoe styles like snakeskin booties or white booties go, too!

What Ankle Boots Go With Black Jeans?

When it comes to wearing boots with black jeans, you’ve got lots of options. We love stacked-heel wedge booties, as well as heeled ankle boots with leather uppers. Slip-on sneaker booties are great, too, if you’re going for a sportier look.

How To Wear Ankle Boots To Work


Think ankle boots are only good for the weekend? Think again. These versatile shoes can be worn any day of the week, even when youre heading into the office. All you need to do is keep your look smart and chic to elevate your ankle boots to be business-appropriate. Start by selecting a pair in leather. The smooth and clean finish will provide a polished aesthetic thats ideal for work. Then, partner your boots with pieces that are both serious and stylish. A pair of tailored pants, fitted shirt, and longline blazer makes an excellent choice, but dont be afraid to try a dress or a suit .


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Maxi Dress & Ankle Boots = The Dream Team

This duo is the ultimate autumnal chic look and is a favorite of celebrities like Rosie Huntington-Whiteley and Katie Holmes. Ankle booties can make any of your favorite summer maxi-dresses more wearable for autumn and winter.

The key to carrying off this look is to choose ankle boots in monochrome or earth tone colors.

Ankle boots with a high heel achieve a sophisticated vibe, whereas flat ankle boots can help dress down this look to make it everyday appropriate.

Myleene Klass, Emma Roberts, and Kristin Cavallari in maxi dresses and ankle boots

Choose A Waterproof Ankle Boot For Its Practicality

Waterproof boots dont have to look dull and unstylish. Opt for a balance of fashion and function by choosing one of these styles that are highly recommended by our readers.

A timeless black boot such as the Blondo Villa pictured above will ensure you look fab anywhere from the streets of Paris to London.

Youll want to look your best when you travel! Read my travel tips to Pack Light Stylishly!

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How To Wear Booties With Mom Jeans

I usually loathe mom jeans. I just dont think they look that great on my frame because not only am I short but my legs are super short too for my body! But even still, I want to discuss mom jeans because theyre super in style right now.

In my experience, Ive found that a skinny and high shaft tends to look the best with mom jeans. The contrast of the wide leg and skinny bootie shaft makes for a great, flattering combo!

Embrace The Western Look

How to Wear Booties and Ankle Boots

For the bohemian fashionista, cowboy ankle boots can help create a laid-back retro-inspired look. For a fashion-forward look, choose a dress in an electric color like yellow or purple, and add a matching belt to fully embrace the modern western aesthetic.

This style of ankle boot tends to feature a low and wide heel, making them ideal for wearing for hours on end while youre running around town.

If you want to stay true to the heritage of these boots and embrace your inner cowboy, chose a pair of western-inspired ankle boots in a tan brown or distressed black.

Rachel Stevens, Karina Smirnoff, and Katharine McPhee go western in printed dresses and western boots

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Over The Knee Boots Outfits

Over-the-knee boots are the sexiest type of boot that you could wear, in my opinion. Like with knee boots, you either go bare-legged or wear something very form-fitting. Below Ive shared three completely different ways to wear this type of boot. You can wear over-the-knee boots with black skinny jeans, a dress or a skirt. As you can see going bare-legged is easier to wear. Depending on the type of over-the-knee boots you get they can be a little difficult to put on at times and you definitely dont want any cloth bunching up because that is very uncomfortable.

If you do opt to wear a dress or skirt, make sure that its not super short or too tight. You want to keep your outfit classy and a super short skirt and very high boots are the opposite.

Over the Knee Boots with Dress

This is one of my favorite dresses with boot pairings. The light shirt dress is a great contrast to the heavy over-the-knee boots. This outfit has an overall nice appeal because the shirtdress is more conservative and the boots are sexier. The balance between the two make for a very stylish look. Also, the vertical lines on the shirtdress create the illusion of looking taller.

To complete this over-the-knee boots outfit I added a large structured bag to keep this outfit of the dressier side.

Skinny Jeans with Over the Knee Boots

Skirt with Over the Knee Boots

Black Flat Over the Knee Boots Outfit

Sweater Dress with Over the Knee Boots

Stay Stylish,

Dont Treat Your Leggings Like Tights

It can be mighty tempting to slip on those fleece-lined leggings between a skirt or dress and cute booties mid-winter, but were not particularly big fans of this combination. Realistically, wearing your leggings as tights all too often ends up looking bulky, especially at your middle where the waistbands layer atop one another. Not to mention, they can add extra heft to your legs when paired with boots. Lucky for dress-lovers, there are plenty of fleece-lined tights available for a look thats just as warm and all the more streamlined and flattering.


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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 Sleek Pair With Wide

How To Wear Ankle Boots With Skinny Jeans

The most basic yet classic way to wear ankle boots? Under slightly cropped, wide-leg jeans. To really nail the look, choose a black pair that is tighter and hits higher up on the ankle , which will work to create a seamless line and elongate your legs. To create a French-girl aesthetic, wear other pared-down pieces with your jeans and boots, such as a sweater set.

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Outfit Ideas For Wearing Ankle Boots With Cropped Jeans

Cropped jeans or pants can make you look shorter and wider than you are, so a great way to mitigate this is to team them with a sock boot. Sock boots are tight around the ankle and sit neatly inside the leg of a cropped jeans.

Get the look :

Get the look :

Get the look :

Get the look :

Get the look :

How To Wear Ankle Boots With Jeans Neutral Color

Combine them with dark wash skinny jeans, a jacket layered over a tunic top, or long button up top. Alternatively, you could also pair with black leggings. Leggings can be worn as pants so long as your top is long enough to fully cover your crotch and bottom. Another option is to find legging style knit pants!

Where to wear: Columbus | Amsterdam | Portland

Shop more tan ankle boots:Nordstrom |

Heres the list of the best skinny jeans according to our readers!

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Add An Oversize Sweater Over Your Workout Gear

How to Wear Ankle Boots &  Booties

Sometimes, a busy schedule means finding ways to wear your workout ensemble for the rest of the day. Our tip for heading to brunch in this mornings yoga pants and your cute new booties? Be sure to add a thigh-grazing knit into the mix. The sweater will help to bridge the gap between your structured ankle boots and your techy leggings, so you dont look like you got dressed in the dark and accidentally pulled out the wrong legwear.

Shop similar styles: A New Day sweater Free People sweater Cotton Citizen sweater Lilybod leggings Summersalt leggings All Access leggings Bella Vita boots Linea Paolo boots Kork-Ease boots

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Avoid Bunching At The Ankles

Slouchy fabric around the top of your boots is going to give off major 80s leg warmer vibes . Plus, all that excess can make petite frames or short legs look squat. The solution may be tucking your lengthy leggings into a pair of slightly taller boots, or it might be discreetly rolling the hem, so they fit just right. If you find yourself dealing with pooling fabric often, you should consider taking your leggings to a tailor to have them hemmed to just the right height, once and for all.

These Booties Go With Everything

I tend to wear a lot of colorful prints and dresses to the office and am always looking to find shoes that will go with items I already own to maximize use. This classic black shade was just the solution. Whether you plan to sport them with a bold maxi dress or simple skinny jeans, they have a way of pairing perfectly with almost any outfit.

But in my opinion, these Chelsea booties are clearly designed for more casual activities, like walking around a city or strolling through Central Park. They feature more of an edgy look, so if your style leans more “super feminine” or youre searching for options for a swanky dinner with friends, I would keep shopping.

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Shacket + Skinny Jeans + Booties

We all love our cozy shackets in the cooler months! Pair your favorite shacket with a graphic tee, dark denim skinny jeans and black heeled booties for an effortlessly cool look.

This is an outfit I would wear in the Fall to drop my girls at school and head to work meetings! I love that it looks stylish and trendy without being too forced.

Try recreating this look with a sherpa jacket as well to mix it up! The options are endless here and you are guaranteed a chic look.

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