Versatile and Comfortable Ankle Boots Outfits

The ankle boots are certainly a worthy investment piece and not just because they are trendy, but also because of the wearing advantages that they give. Such as:

  • ankle boots give you a far more sturdy/supported feeling than, for example, heels do;
  • you can wear socks with them to avoid possible blisters, etc., so regarding comfort and wearability they have more versatility;
  • the ankle boots work well paired with a number of outfits (like jeans, other skinny pants, khakis, shorts, dresses, skirts, any color,) instead of being limited.
  • ankle boots have the little scoop in the front that really helps elongate your legs.

So, what is the key of the ankle boots fashionably flexibility? The answer is probably the greatest number of types.

There is a huge list of ankle boots depending on the style of the heel (like wedge, heel, flat) or the toe-bed shape and type (such as pointed, rounded toe, closed-toe, peep-toe, broad-rounded, roper-shaped toe-beds, etc.).

How to Wear Booties

How to wear and style:

  • the low block heeled ankle boots

The low block heeled ankle boots are the everyday go-to booties, which stay the most comfortable whether you wearing them for 2 hours or 12.

Wear them with rolled up jeans, swing dresses, skirts, leggings, jeggings, and straight jeans mixed with less formal tops.

  • The high block heeled ankle boots

The high block heeled ankle boots

Wear them with just about anything, including jeans (both rolled up or even tucked in), skirts, dresses, leggings and a flashy shirt, or a tight mini skirt and black top.

  • The wedge heel ankle boots

The wedge heel ankle boots are the great alternative for the everyday stacked heel booties.

They pair nicely with rolled up jeans.

  • The stiletto heel ankle boots

The heeled booties are always more dressy, so stiletto ankle boots work better for dressier outfits worn at night or for a polished daytime look.

  • The no heel/flat ankle boots

The no heel/flat ankle boots are the perfect everyday boots.

They look cute with swing dresses and/or shorts and rolled up jeans.

  • The pointed toe ankle boots

The pointed toe ankle boots always give you a dressier look.

They look cute with black tights or leggings tucked in.

  • The rounded-toe ankle boots

The rounded-toe ankle boots can be dressy or casual depending on the material, embellishments, or shaft-height.

If we speak about the materials, then usually ankle boots are made of suede, leather or faux leather.

The ankle boots are designed for many purposes and can be worn, for example for the weekend trip, on a date, for the office, to clubs/bars or the dinner with the family.

Today you can find a wide range of colors of the ankle boots either solid-colored or multi-colored. But the most wearable, versatile and most practical color combinations are black, brown and taupe.

How to Wear Booties with Jeans

How to wear the ankle boots with jeans? There are a few great ways to wear ankle boots, so they are flattering you:

  • tucked – creates a long, lean leg line;
  • rolled hem – rolled or double cuffed jeans will keep your ankles from looking wide (this look works best with skinny jeans because the straight-legged or wider-legged jeans can shorten your leg line when rolled);
  • cuffed – fold them inside, so they seem the perfect length. It will keep your ankles looking as slim as possible;
  • half cuff – pairing booties with half cuff jeans will make you look effortless and a little haphazard.

Make a note of these  few tips on how to wear if you have muscular-ish calves:

  • wear ankle boots with straight leg jeans that you can pile a little around the mouth of the boot before tucking it in to create a long, straight line from heel to hip;
  • if your ankle boots are skin-tight, they make your legs look disproportionate. So aim for booties/boots that don’t cling to your ankles;
  • ditto the black tights.

Or if you are short:

  • look for booties with a short shaft (it may not seem like a lot, but at petite height, an extra half inch of material going past the ankle can make a drastic difference in how it affects your proportions);
  • look for booties with a tighter opening (it creates a longer visual line of your leg) compared to something like foldover combat boots which break this line;
  • heels always help (especially if there are no patterns/details in the front panel that would break the flow);
  • matching the color/hue of the booties with your pants or tights (e.g. Black booties with black pants or a dark wash jean);
  • look for boots with some kind of heel to elongate the leg;
  • also, boots that curve in the front will lessen the shortening effect.

What to wear with ankle boots:

  • matched colored tights – try brown tights with brown boots, gray with gray, or mustard with your light brown boots;
  • colored tights – it will incorporate some color into your outfit;
  • dress – keep the hem of your dress above your knee to create the longest leg line possible.
  • pencil skirt – choose a light, neutral boots to elongate the legs and keep the outfit feeling balanced;
  • shorts and stockings – even for work it won’t get you a fashion boo-boo if you combine it with not high heeled ankle boots;
  • knitted dress with black tights;
  • black skinny jeans;
  • maxi skirts;
  • knee-length skirts;
  • dark denim shorts, opaque black tights and a cute top;
  • boyfriend fit jeans, cuffed to the top of the boot.

Outfits with Booties

For the everyday fall look, go for a combo of cropped jeans and denim jacket, worn atop of black turtleneck. Add fabulous golden ankle boots and trendy hat, and you’re ready!

On drizzling days, opt for a cozy and comfortable set of cropped jeans, warm socks, and bright red leather ankle boots. Team up it with a nice sweatshirt and a cute umbrella.

Add some French flair to your look with an ensemble of black button-down skirt and striped white&black sweatshirt. Add ultra-hot black leather heeled ankle boots and little leather purse to end the look.

Mix fabrics and textures to create your unbeatable style. Classic white shirt and cropped jeans look amazingly well with a fur coat, brimmed hat and beautiful floral ankle boots.

Who said that ankle boots are for fall only? Combine them with skinny black jeans, nice gray turtleneck and warm long cashmere coat, and you’ll get a perfect winter outfit. Simple yet chic!

Stylish black leather ankle boots is a great addition to this smart men’s street style set. The skinny black jeans, the striped shirt worn atop burgundy turtleneck and warm classic coat create a perfect combo with a cool baseball hat.

For an extraordinary alternative to traditional office look, go for this black and white combo of the dressy blouse, ripped jeans and a super stylish white low-heeled ankle boots.

You will never go wrong with an all-black look. Go for a nice dressy blouse, leather skirt, and a pair of chunky heeled ankle boots. End up the look with tights, cute purse, and matching accessories.

Keep it cool and stylish with a pair of skinny leather pants and an awesome black moto jacket. Add a dope black ankle boots, and your perfect rock outfit is ready.

For a more casual option, choose this amazing summer outfit. Funny T-shirt and light floral skirt team up perfectly with the brown chunky heeled lace ankle boots. Add a brownish leather purse and sunnies to finish the image.

Try a pair of ankle booties in cognac—the color of the season. Style them with black ripped skinnies, brimmed hat and a warm cashmere coat for the perfect fall look.

For the edgy dress, style a long dark gray cashmere coat and cropped pants with a trendy hat and a pair of heeled ankle boots. Complete the look with a cute purse.

Dress down a gentle pale pink suit of the trench coat, cropped trousers and—that’s right—slipping into a pair of cut velvet ankle boots instead of heels. Finish the set with a black brimmed hat and trendy sunglasses.

With a solid base of a crispy white sweatshirt, light blue cropped jeans, and suede ankle boots, you can mix and match everything from a casual day look to really cute feminine date outfit.

When in doubt, keep it classic with a black knitted dress and low-heeled ankle boots. Complete the look with a metallic necklace, wrist watch, and trendy sunnies.

Pair the chunky heeled ankle booties with an amazing light dress, worn under a warm leather jacket for a cute layered fall outfit. Team it up with a knitted scarf and pretty purse to end the image.

A super-low ankle boot is a modern alternative to traditional flats. Just combine them with all white set of crop top, crop pants, and trench coat to create a trendy autumn go-to look.

Try something new this season and try a pair of low heeled ankle boots and an oversized overcoat with colorful details. This look will become more interesting teamed up with a bright purse.

Play with color this season and style a plain sleeveless brownish coat with leopard print stiletto ankle boots. It’s not just an easy way to dress up, but it’s also a great idea for cold days.

When heading to the office, reach for short classic pants, a dressy blouse worn under a cardigan and chunky heeled ankle boots. Grab a smart handbag, and you’re good to go!

Here’s a very simple, yet pretty outfit that you could throw on in seconds and wear on a cool summer day. The cropped jeans and matching jacket look perfectly with low ankle boots and leather purse.

This cool combo of pointed toe low block heeled ankle boots ant black leather jeggings makes your legs miles longer! Just add a simple white T-shirt, knitted cardigan, and a little black purse to complete your look.

The silver ankle booties are a great option when you want to create a cool street style for weekends. Just pair them with plain black leggings, black turtleneck, and rock T-shirt.

For weekend activities this fall fashion an outfit of a loose sweatshirt, coat, and black ripped skinny jeans. Finish it off with a pair of chunky low-heeled booties that keep your feet just as comfortable as your favorite flats.

If you like to stand out of the crowd, then make a note of this ensemble of hooded jacket, long skirt, and low-heeled red suede ankle boots. Stylish and warm.

This dressy burgundy polka-dotted shirt looks gorgeous paired with the button-down denim skirt. Combine it with a pair of stylish short red ankle boots for a simple girly spring look.

Do you like the fashion of the 80s? Then go for a combo of black flared pants, knitted sweater and a pair of comfortable milky white ankle boots. Functional and cute at the same time.

Add a bright yellow coat to the combo of short floral dress and black tights, and you’re totally set for cold spring days. Finish the look with a pair of black low ankle boots and trendy sunglasses.

Top this smart outfit (of black leather shorts and dressy crispy white blouse) off with a pair of classy ankle boots. Complete the look with black tights and the matching purse.

The long checked gray cashmere coat, black ripped jeans, and a warm burgundy sweater is a great option for cold days. Complete this look with stylish flat burgundy ankle boots and big leather bag.

If pink’s not your thing, you can always choose a pale gray for a win-win look. Wear a combo of skinny jeans and shirt for a simple casual look. Add leather purse and taupe ankle boots, and you’re set!

Most color combinations pair beautifully, as long as one chosen hue is light, while the other remains slightly darker. So try to team up classic beige trousers with a brown textile turtleneck and beige ankle boots.

Modernize your usual office look by opting for a cute dress worn atop classy blouse. Finish your outfit off by adding a pair of heeled booties and a matching leather purse.

Keep it simple with skinny jeans and the nice sweatshirt worn under a warm jacket. Pair it with black leather ankle boots that add a bit of style to your weekend casual outfit.

If you need an idea of simple and comfy spring outfit, then try this combo of a high-waisted cuffed blue jeans and fun black T-shirt. Complete the outfit with a backpack and a pair of cozy low ankle boots.

For an evening out, style your combo of decorated with flowered jeans and cute sweater with a pair of Alexander Mcqueen’s low ankle boots with floral embroidery.

This light-gray trench coat looks super hot and stylish worn atop black crop top and wrap around mini skirt. Complete an outfit with a pair of classic ankle boots and beautiful purse.

For everything from the office to a date night, there’s no easier way to look stylish then pairing your outfit with a pair of heeled beige ankle booties and a cropped mint jeans.

No matter what you wear on top, make sure you own a pair of trendy pink ankle boots. Team up it with crop deep blue jeans and cool leather purse and your smart everyday set is ready.

Anchor your urban uniform with an ensemble of black denim mini skirt, sweatshirt, and long pale gray coat. Jazz it up a little bit with a pair of shiny heeled ankle boots.

Do you want an idea of totally casually and cool fall look? Then mix a cropped denim and plain black textile sweater and a pair of snakeskin low-heeled ankle boots.

Keep it chic with plane cuffed denim, white&black striped sweatshirt and trendy brimmed hat. Add a pair of flat ankle boots to help you weave through those crowded city streets.

Go for cozy red sports pants and warm brownish jacket for a fusion sporty street style. Add a pair of low heeled ankle booties and cool red purse to finish the look.

Choose the classic combo of crop deep blue denim and black leather jacket to create a cool fall set. Pair it with black socks and low heeled ankle boots to complete the look.