Ankle boots are some of the favorite footwear options of the late 2010s, and it is not that hard to understand why. Contrary to popular belief, ankle boots go along flawlessly with any outfit, whether one needs something cozy to wear on a long day at the office/ university, or is looking for a night out-approved fancy outfit. The key behind the perfect combination lies in the structure and material of the ankle boots you choose.

How to Wear Ankle Boots

Knowing how to wear your ankle boots with any outfit is of primary importance, as despite what a simple accessory piece the ankle boot seems to be, it does require certain style rules, if you want to always look impeccable. To give you a wider perspective on this iconic fashion statement, we have put together the dos and don’ts of wearing ankle boots with every outfit. We have also rounded up the best ankle boots to show off for winter 2018-2019 (or even up until spring 2019!).

Women’s Ankle Boots Style Guide: Contents

Best Ankle Boots to Get for Winter 2018-2019
How to Wear Ankle Boots Right

Best Ankle Boots to Get for Winter 2018-2019

So if you have decided to step into the ankle boot game, below you’ll find the best ankle boots for winter 2018-2019 from top famous brands and fashion retailers.

1. Gucci Queercore-Embellished Leather Ankle Boots

Combat boots are one of this fall’s biggest trends, and we all know that when there’s a trend around, Gucci has surely revisited it through its own extra-fancy lens. Eighties-inspired and embellished with the brand’s Dionysus’ buckles, Gucci’s combat ankle boots are the best for fall, winter, and spring 2019, for sure! Get yours at Net-a-Porter!

Best Ankle Boots for Women: Gucci Queercore-Embellished Leather Ankle Boots

2. Miu Miu Knit Sock Ankle Boots

This is one of the best pairs of ankle boots for winter 2019 for several reasons. First, it’s perfectly elegant and classy, and the black color will make great pairs with practically any outfit. Secondly, the extra factor of the logo-printed sock style makes it super-dressy and avant-garde, which means you can easily take these ankle booties from day to night! Go get your pair from LuisaViaRoma!

Best Ankle Boots for Women: Miu Miu Knit Sock Ankle Boots

3. Mansur Gavriel Pink Glitter Ankle Boots

Pink is the color of passion and, when paired with glitter, it could make anyone happy within seconds. These pink and glitter ankle boots are just the perfect answer to the pink and glitter 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 (always first yourself!). You can find them at Forward.

Best Ankle Boots for Women: Mansur Gavriel Pink Glitter Ankle Boots

4. See By Chloe Zip Ankle Boots

Do you ever find yourself trapped in the sweetest Seventies-inspired daydreams? Well, if the Seventies and suede materials are your bread and butter, you will always find comfort in any of See By Chloe’s ankle boots. This pair of zip-detail ankle boots is utterly fashionable, whether you would like to sport it at a Seventies-themed party or on a (non-so-)casual night out with friends. You can get it from Net-a-Porter.

Best Ankle Boots for Women: See By Chloe Zip Ankle Boots

5. Isabel Marant Cowboy-Style Ankle Boots

From one extra factor to another, going unnoticed will be impossible with this cowboy pair of Isabel Marant ankle boots. Earth-toned and easy to wear, they are made for walking and dancing, indeed! Find yours at MyTheresa!

Best Ankle Boots for Women: Isabel Marant Cowboy-Style Ankle Boots

6. Pink Curved Ankle Boots

Who says ankle boots can’t be cute? Reike Nen’s pastel pink booties are perfect for any day-to-day activity, especially if you are always on the go and need something that fits and feels always cozy even at the end of the day. Grab yours at Farfetch!

Best Ankle Boots for Women: Reike Nen Pink Curved Ankle Boots

7. Alaïa Appliquéd Booties

Of course, one of this fall’s best pairs of ankle boots had to be Alaïa’s! If you are looking for something unconventional to leave everyone speechless, these cut-out ankle boots are the way to go! You can find their pointy figures and appliquéd leather at Net-a-Porter.

Best Ankle Boots for Women: Alaïa Appliquéd Ankle Boots

8. Chie Mihara Printed Ankle Boots

If too deconstructed or too metallic is just too much for your, Chie Mihara’s patterned suede and leather ankle boots are the best to elevate any outfit. Farfetch has got you covered, if this is the ultimate pair of ankle booties you’ve been looking for!

Best Ankle Boots for Women: Chie Mihara Printed Ankle Boots

9. The Cut-Out Bootie

We know this pair of ankle boots will make all those vintage style lovers fall deeply in love with the cuts and sophisticated structure. Refinished with a tonal lacing, they are also extremely cozy! You can buy this pair in any of the three colors at Nordstrom.

Best Ankle Boots for Women: Vince Camuto Cut-Out Ankle Boots

10. Dr. Martens Embellished Ankle Boots

Embellished with lovely floral embroideries, this pair of ankle boots perfectly exemplifies Dr. Martens’ fall and winter season. Combat-style and wholeheartedly glam-rock-approved, they could easily complement any style. This gorgeous pair sells on Shopbop.

Best Ankle Boots for Women: Dr. Martens Embellished Ankle Boots

11. Rag & Bone Cannon Ankle Boots

Is there anything more classic than a pair of black leather ankle boots designed by Rag & Bone? Probably not! We officially declare this pair of laced and zipped leather boots as the most effortless on this list. They are available through Shopbop.

Best Ankle Boots for Women: Rag & Bone Cannon Ankle Boots

12. The Red Lipstick Leather Ankle Boots

Crafted in Italy from soft leather and refined though the signature kitten heels, Tabitha Simmons’ red ankle boots are already one of this year’s biggest accessory trend, and we won’t be surprised to spot them at every fashion icon’s feet in the months to come. They are available at Farfetch.

Best Ankle Boots for Women: Tabitha Simmons Red Ankle Boots

13. The Classic Leather Chelsea Boots

Feeling special with Common Projects is, pardon the pun, not uncommon. That’s mainly because, besides the uncanny quality of their accessories, their footwear designs are stamped with gilded serial numbers on the sides. This pair of ankle boots, which is as classic as elegant, features the brand’s serial numbers along with the finest leather structure fabricated in Italy. You can easily find yours at Net-a-Porter!

Best Ankle Boots for Women: Common Projects Ankle Boots


How to Wear Ankle Boots Right

Wearing ankle boots with any outfit and for any occasion may be perceived as a difficult task, as many believe that ankle boots are a definite no-no on all fronts unless one is blessed with a pair of super-long legs. Many women under 5’1’’ have made up several excuses to not wear them, let alone the fact that they are often advised not to buy them because they won’t flatter their petite figures.

That’s however incorrect. There are a few useful tricks that will make any petite figure appear elongated with ankle boots as well, and we are here to reveal them!

• Proportion is key in fashion, whether you are about to wear your favorite pair of ankle boots or not. When showing them off, however, we suggest making sure the silhouette is well balanced with a relatively long trench coat or blazer, depending on the season, and a pair of cropped pants. They will easily break up the line of your legs, and you will instantly look slender.

By the way, using a long trench coat is a trick we suggest whenever you have to wear a pair of flat shoes, as well!

• Colored ankle boots are cute, that’s true. But so are coherent outfits that don’t break the figures. Make sure your ankle boots and tights or trousers share the same color tones, as monochromatic combinations are key, too!

• Back to proportions, always keep the following rule in mind – “the shorter the ankle boots, the longer hemlines you can opt for (and vice versa).” Use this rule also to remind yourself to always buy ankle boots that, most and foremost, fit your feet and ankle right. Shaggy ankle boots, for example, could easily weigh you down visually.

As for those who are tall and think they can wear ankle boots whenever and however they like, you’d better think twice! The industry is filled with different ankle boot styles, colors, and structures aplenty, meaning that not only isn’t it easy to find the perfect pair of ankle boots, but also pairing them according to the right occasion.

What to Wear Ankle Boots With

How to Wear Ankle Boots with Jeans

Ankle boots and jeans are two different protagonists of the same love story, and we can’t help but adore ‘those’ two whenever they are together. Although wearing ankle boots with jeans is pretty much always a good idea, there are a few dos and don’ts it is always better to take into consideration when channelling them.

First of all, jeans are so diverse in their styles and cuts that even tucking them might cause indecisiveness. Speaking of this, just follow this simple golden rule: never tuck loose fitting, boot-cut or bell-bottom jeans in your ankle boots.

When in doubt, always opt for a pair of tight skinny jeans and have fun tucking them in! Otherwise, pick a pair of cropped jeans that will always look amazing with ankle booties.

How to Wear Ankle Boots with Jeans

Another ankle boots-jeans golden rule is that of investing in a good pair of brown ankle boots to wear with any pair of jeans, from the lightest to the darkest. Such a combination will give you something fancy to don on a daily basis, whether you are about to spend the day at the university or at the office.

For a night out with friends or on a special date, opt for a pair of bell-bottom jeans paired with a pair of block-heeled ankle boots, and you will instantly feel like a Seventies-inspired queen!

Keep in mind that tight-fitting pants or leggings, or high-waisted skinny jeans or tailored pants pair perfectly well with ankle boots, visually elongating your legs and slimming you down.

How to Wear Ankle Boots with Jeans

How to Wear Ankle Boots with Skirts and Dresses

As with being petite, wearing ankle boots with skirts and dresses is something many perceive as a bad idea. Well, they couldn’t be more wrong! Ankle boots and skirts always go along together fabulously, especially when:

• The skirt is midi or longuette, as such a combination will flawlessly elongate any figure while at the same time adding an always flattering overall classic touch to the entire outfit;

• The dress runs a little below the knees and is flowy and A-lined in its cuts, as it could help any look find its glorious way into the Hall of Fame of romantic outfits;

• The dress or the skirt is maxi and features a sensual slit on one (or even both) side. Here proportion and balance surely rejoice.

• Your ankle boots are in a neutral color, matching your skin tone, which will create the effect of an elongated figure, breaking any harsh contrasts.

Extra tips: favour skirts that show some skin over those that don’t during springtime, and never forget to match your ankle boots and tights or, alternatively, the colors of your skirt and your tights during fall.

Another amazing tip is pairing black ankle boots with black opaque tights to visually elongate the figure. On the other hand, it’s not a good idea to wear colored ankle boots with black opaque tights, as this will create a stark contrast, breaking your nice proportions.

How to Wear Ankle Boots with Skirts and Dresses

Night Out-Approved Ankle Boots

What if we tell you ankle boots can come rescue any night out look, particularly when something elegant yet extremely cozy is needed? Dancing Queens, rejoice! Ankle boots are the best night out footwear option for anyone who could (and actually does) spend hours dancing the nights away, as they make it possible to move freely from 11.00 PM to 06.00 AM without experiencing feelings of intense sore feet.

If you are willing to invest in a good pair of night out-approved ankle boots, whether you know you will pair them with a pair of edgy trousers or a dress, just remember to focus on the heels or on the one-of-a-kind details your booties will feature!

Bejewelled heels, cuts on the sides, or quirky fabrics such as metallic leather or heels are always a go-to whenever it comes to a fancy night out outfit, and ankle boots just work together so well with any of these details. You’ll just need to complement your look with just a little bit of self-confidence, et voila! You’ll be ready to rock the night away!

Photos via @mikutas, @vivaluxuryblog, @bartabacmode, @aylin_koenig