How To Style Ankle Boots Like The IT Girls This A/W

It’s the time of the year when we get to throw on our favourite pair of ankle boots from day to night! This is always my favourite season and there’s no denying the power of a pair of ankle boots. Ankle booties are always the ultimate pull-on-and go Autumn/ Winter outfit that will never let you down regardless you’re heading to the office meetings, running errands, or keep it casuals for a cocktail session with your friends. In short, they are literally the life safer which can elevate your daily outfit instantly. Today, I’ve rounded up some outfits which you can style it together with ankle boots to create that BAAAM combination! Without further do, let’s check out how these stylish IT girls styled their ankle boots this season!

Aimee Song
Aimee creates that fun and high fashion look by pairing her multi-colored striped sweater, mini leather skirt and a pair of burgundy leather ankle boots.
Currently Caro
She teams up a black lace long sleeve top with a frayed hem a-line denim skirt and a pair of black ankle booties to create that elegant and edgy look!
The Rue Collective
The coordination of a dress and a pair of ankle booties give you that cute and girl next door look.
Michella Choi
Michellea anchored her off-duty uniform with a button down shirt, a pair of skinnies, a trench coat and a pair of printed ankle chunky boots
Michella Choi
Create that edgy girl vibe by channeling all black outfit including the ankle boots. Michella finish off the look by toping off a nude trench coat and a black baseball cap.
Chantal Li
Who says ankle boots can’t be feminine? Chantal creates a lovely and edgy ensemble by wearing her ankle boots with a black oversized sweater with a white patterned midi skirt.




Anchor your office or running errands look in style with this first combination.

For top, I’ve picked the most on-trend floral embroidered blue button down shirt. Since it is a button down, it creates that work appropriate look yet maintaining some fun and sassiness.

For bottom, I will be opting a pair of denim skinnies which come with this ripped knee hole detailing.

To beat the cold, layer this outfit with a beige lapel double breasted trench coat.

Lastly, slip into a pair of nude pointed toe ankle boots with rivets embellishments and carry a black leather handbag to call it a day!


Beige Lapel Double Breasted Trench Coat

This beige lapel double breasted trench coat is a timeless piece that can be worn season after season.

$48.00 USD


Flower Embroidered Blue Button Down Shirt

Spice up your everyday look with this blue button down shirt that features gorgeous and exquisite flower embroidery. Regardless you’re styling for work or casual outing, this shirt definitely will complement your look!

$29.99 USD


Dark Blue Skinny Denim Jeans Featuring Distressed Knee Hole

A pair of skinny jeans featuring dark blue hue and a distressed knee hole is a wardrobe staple which can transform from season to season!

$28.40 USD


Nude Rivets Embellished High Heel Boots

A pair of pointed toe high heel boots showcasing gorgeous rivets detailing which definitely add a splash of edginess.

$50.99 USD


Black Embossed Faux Leather Handbag Featuring Detachable Shoulder Strap

This black embossed faux leather handbag featuring detachable shoulder strap is a perfect handbag for the office. Stuff in all your essentials including files without the need to worry of ruined documents.

$14.00 USD


If you lust over monochrome look or want to channel the edgy chic look, this combination is PERFECT for you!

For top, I’ve opted a black cold shoulder top. Then, I will be teaming it with a pair of black skinny jeans with distressed detailing.

For shoes, I’ve picked a pair of black pointed toe high heel ankle boots.

If the weather is chilly, layer a black and grey color block baseball jacket.

To add the athleisure vibe, wear this cute yet edgy black “somebody to love” baseball cap.

Last but not least, carry a black leather backpack to complete the look!


Black and Grey Color Block Baseball Jacket Featuring Front Zipper Detailing

This baseball jacket featuring black and grey color block, front zipper detailing is everything you need to create that edgy athleisure chic look this A/W!

$27.50 USD


Black Cold Shoulder Knitted Fitted Top

This black knitted cold shoulder which is in a fitted silhouette is the perfect daily staple which you can easily transform into different look depending on the bottoms you coordinate it with.

$21.99 USD


Black Skinny Distressed Jeans

Nobody can ever live without a pair of black jeans. This black jeans is in a slim fit silhouette which will flaunt your curves. The distressed detailing give the bored pair of jeans an edgy accent.

$34.99 USD


Black Pointed Toe High Heel Boots

A pair of minimal and sleek black pointed toe high heel boots is every girl MUST have item this Autumn/ Winter!

$49.99 USD


Black Somebody To Love Baseball Cap

Elevate your daily look with this cute and fun baseball cap with a printed logo and ‘somebody to love’ quotes.

$7.92 USD


Black Leather Backpack Featuring Rivets Embellishments

A black leather backpack featuring rivets embellishments on both sides and a flap closure.

$69.96 USD


Looking for something in between fancy for a daytime look, check out this combination.

Slip dress is definitely having a HUGE moment this year and if you do not wear it well, you will look like wearing lingerie out from your house.

For this combination, I will be layering a black plunge v long slip dress which featuring a high slit over a white collarless button down shirt.

The button down shirt will create the perfect balance for the slip dress and even make it appropriate for formal event.

For shoes, go for a pair of black suede chunky heel ankle boots as the suede material gives you a splash of luxe and elevate your look instantly.

Finish off this look by wearing a pair of minimal and sophisticated gold hoop earrings with circle pendant and carry a black leather chain crossbody with quilted texture.


White Collarless Button Down Shirt

A white shirt featuring a stretch of buttons on the front and a collarless crew neck.

$22.00 USD


Black Plunge V Long Slip Dress Featuring High Slit

This black long slip dress features a plunging neckline which will accentuates your bosom. The showcasing of the high slit on the side will shows off your slender legs and adds a seductive touch.

$23.00 USD


Black Suede Thick high Heel Ankle Boots Featuring Buckle Straps

A pair of black suede ankle boots showcasing thick heel which gives you the ultimate comfort to walk all day long and a buckle strap closure.

$61.60 USD


Gold Hoop Earrings Featuring Circle Pendant

Elevate your minimal look with this exquisite pair of gold hoop earrings with circle pendant beneath the hoop.

$6.99 USD


Black Leather Chain Crossbody Featuring Quilted Texture

A minimal yet sophisticated black leather crossbody featuring chain shoulder straps and quilted texture.

$23.99 USD


Channel the fall florals and your inner romaticism with this edgy yet romantic look.

For top, I’ve chosen a simple black off the shoulder long sleeve top to flaunt some skin in this cold weather season.

Then, I will be coordinating it with a floral patterned long chiffon skirt.

When the weather turns chilly, layer a black leather jacket over the off shoulder.

To amp up the glam, wear a pair of long gold hoop earrings.

To complete this look, carry a color block envelope crossbody and a pair of brown chunky heel ankle boots with rivets detailing.


Black Leather Jacket

Upgrade your daily cold weather look with this black leather jacket featuring front side zipper, belted on the hem and a lapel design.

$169.00 USD


Black Off The Shoulder Long Sleeve Top

A minimal long sleeve top in black hue featuring a off the shoulder neckline which will flaunt your sexy collar bone.

$15.00 USD


Chiffon Floral Pleated Long Skirt

Channel fall florals this cold season in this gorgeous romantic chiffon floral pleated long skirt. The long chiffon material gives you the ultimate comfort to transform from a day to night look.

$28.99 USD


Gold Long Hoop Earrings

This pair of gold long hoop earrings is the perfect pair for those minimalist out there! It adds a splash of sophistication to your simple and sleek everyday look!

$6.99 USD


Color Block Leather Envelope Crossbody

An envelope inspired crossbody that showcases a flap closure and beautiful color block effect.

$18.99 USD


Brown Faux Leather Chunky Heel Ankle Boots Featuring Rivets Detailing

A pair of brown faux leather boots showcaases chunky heels, giving you the height while maintaining the comfortability. It also showcases a side zipper which make it easier for you to slip in and out. The rivets detailing adds a splash of edgy accent to the shoes.

$44.00 USD


For those girls who always wear skirt regardless of the season, this is the ultimate look for you.

For top, I’ve picked a nude knitted cold shoulder top so that you can wrap yourself in style and keep yourself warm.

For bottom, I’ve opted a black A-line skirt which comes with this minimal hoop zipper.

To elongate your look, I will suggest you to go for a pair of matching color high heel boots.

To finish off this look, wear a pair of gold hoop earrings to add a splash of glitz and carry a color block vintage inspired shoulder bag.



Nude Knitted Cold Shoulder Sweater 

A nude knitted sweater featuring cutout shoulder which flaunts your skin without bearing it all.

$25.00 USD


Black A-Line Skirt With Hoop Zipper

This black skirt showcases an A-line silhouette which will complement any body type. The hoop zipper also adds a minimal and sophisticated accent to the skirt.

$18.99 USD


Black Pointed Toe Ankle Boots

This minimal pair of black pointed toe ankle boots will give you spice up your everyday look instantly.

$35.99 USDgold-hoop-earrings

Gold Hoop Earrings

Update your jewellery box with this gorgeous and exquisite pair of gold hoop earrings.

$6.99 USD



Faux Leather Color Block Vintage Shoulder Bag 

This vintage inspired shoulder bag will level up your bag game with its gorgeous color block effect and the cute metal handle.

$24.99 USD

That’s all for today’s topic and I hope you guys are inspired and find this article useful!

Out of these 5 outfits which  I’ve created, tell me which OOTD you will likely to wear?

I would be delighted to hear from you!

Do not hesitate to share with me your styling tips as well!

Stay tuned for more awesome tips as we update on every Monday, Wednesday, Friday and Saturday.

Till next time and don’t forget to be awesome.

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Hello, you! I'm Wendy. A millennial, fashion enthusiast, avid traveller and a music lover! "Art Has No Rules So Does Fashion"
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