• Spend $150+ and receive $25 OFF a belt. Shop Now
  • Free shipping over $200. Easy returns, always.
  • Earn, redeem, and save with Poppy Perks Rewards. Join Now

How to Style Ankle Boots

6-minute read

If there’s one staple your closet needs, it’s a great ankle boot. Our bestselling Two Point Five Ankle Boot has been a mainstay in closets since 2015. The ankle boot style is versatile, comfortable and flattering.  

“The V-shaped topline elongates the leg while making the boot playful enough to be paired with jeans, midi-skirts or trousers,” says Justine, co-founder of Poppy Barley and designer of iconic Two Point Five Ankle Boot. 

Here is a roundup of outfits to wear with your ankle boots. We kept the styling uncomplicated, chic and ready for copying.  

Flat lay photo of the two point five ankle boot

How do you wear pants with ankle boots? 

Don't be afraid to try different pant styles – ankle boots look great with trousers and jeans. No need to choose between slim-leg pants or a more relaxed fit, both look great.  For slim-fitting pants, a cropped hem that hits at the ankle is best. When the details are in the topline of the boot, a higher-cut hemline will lend a proper proportion. 

Ankle boots with cuffed jeansPhoto Credit: Samantha Thompson
Style Tip:

To show off the curve of the boot, cuff  your jeans if they bunch and hit lower than your ankle.

Opting for a bootcut pant or wide-legged trouser will give the ankle boots a modern feel. 

Ankle boots with cropped trousers
Ankle boots with bootcut jeans
Style Tip:

Stylist and Product Designer Kalie recommends, “the pants should hit above the ankle or just above the floor.” 

How do I wear dress pants with ankle boots? 

Ankle boots are a great choice for your work wardrobe or elevated weekend looks. Pairing ankle boots with dress pants is all about playing with hemlines. Select a wide-leg cropped dress pant or a tapered fit that will hit at the ankle. Add a blouse and blazer to complete the outfit.

Ankle boots worn with blazer and dress pants
Style Tip:

Choose a heel low enough heel to make sure your feet are comfortable all day long. “The Two Point Five Ankle Boot name comes from the 2.5” heel height – the perfect combination of height, stability, and all-day comfort,” explains Justine. 

How do you wear ankle boots with a dress or skirt?

There are many ways to pair ankle boots with a dress or skirt. Knee, midi and maxi length skirts all look with ankle boots. Stay away from mini-skirts length hemlines to keep the skirt and boot ratio proportional.

Wearing the boot with a sundress lends a slightly western feel to the boot, while wearing it with an a-line skirt will modernize it. To transition the look from summer to fall, add tights during the cooler months.

Ankle boots worn with an a-line mid-length skirt
Marielle Tehart wearing ankle boots with a dressPhoto Credit: Marielle Tehart for Nettle's Tale
Style Tip:

A midi skirt is the perfect way to show off your ankle boots. It could be a sleek shift dress or a flowy printed dress, just have fun!

Additional outfit ideas to wear with ankle boots;

If you own a matching sweatsuit, try it on with your ankle boots, add a long wool coat overtop and a crossbody bag. You might be surprised with how adorable and put together you look!

Ankle boots paired with socks

What socks should you wear with ankle boots? 

A no-show sock lets the boots take centre stage. Keep the sock below the topline of the ankle boot. For the Two Point Five Ankle Boot, a sock that dips low around the ankle and coordinates with the colour of your boot is best.

Pairing ankle boots with fun tights or socks can look very stylish. The combo is really having a moment and is a great way for your unique style to show through!

For our Two Point Five Years Campaign, we enlisted our team members to showcase the boot as versatile as the people behind it. Our product designer and in-house stylist, Kalie, explains how the look were chosen to suite everyone's personal style and personalities. 

Two Point Five Year Campaign

We worked with what was trending currently – elevated joggers paired with a relaxed cable knit sweater and some pretty gold chains on Kassandra. This "winter whites" look paired really beautifully with the ankle boot in Desert Tan.

Wide-legged trouser jeans were used on Vanessa to show a peek of the toe of the boot and give her the height needed to make long lines. To play with silhouettes, she wore a fitted black turtleneck sweater to balance out the leg of the jeans. 

Doris wore a very simple outfit, showcasing a simple, everyday Two Point Five Ankle Boot look. Skinny grey jeans with and an Olive over-shirt was the perfect look on her.

For myself, I wanted to put a spotlight on the ankle boot in Snake, but wanted to make the outfit contemporary and show some alternative pant shapes. A peg-legged belted faux-leather trousers paired with a basic white tee helped to achieve this look.

Kendall is wearing two looks to show different sides of her personality. The colours of the floral print dress were complimentary to her hair and showed how the boots can be worn with softer, bohemian items in your closet. The structured blazer and faux leather joggers show the business leader side of her personality, as it exudes confidence. The elasticated hem works well with the v-topline on the Two Point Five Ankle Boot.

Justine wore the boots with pleated midi skirt with fitted turtleneck sweater to give the boots a 70's cool vibe, which goes to show how versatile the boots really are. She appears again in a cozy natural coloured sweater and faded black cropped jeans, which again interact with the top of the boots perfectly!


Do you have any other questions on how to wear the Two Point Five Ankle Boot?! If so, please reach out to our concierge team at concierge@poppybarley.com and we’d be happy to help.

Shop The Look

Older Post Newer Post

All Day Comfort

Feel-good footwear in medium and wide widths.

Reformed Pricing

We skip the luxury markups to offer fair prices on high-quality products.

Responsibly Made

Ethically made in audited factories with planet-conscious materials.

Subscribe for early access to new releases and $25 off your first purchase.

The Harley Heeled Sandal Ankle Size Guide

How To Measure:
The Harley Heeled Sandal: Take a tape measure and wrap it around your foot, right below your ankle bone as that is where the strap will sit (see product imagery and fit video for a visual demonstration). This measurement is based on the last adjustment point on the strap.

Size Strap length will accommodate an ankle measurement up to the size below
5 26 cm
5.5 26.5 cm
6 27 cm
6.5 27 cm
7 27.5 cm
7.5 27.5 cm
8 28 cm
8.5 28 cm
9 28 cm
9.5 28.5 cm
10 28.5 cm
10.5 29 cm
11 29 cm
11.5 30 cm
12 30 cm

The Esther Heeled Sandal Ankle Size Guide

How to Measure:
The Esther Heeled Sandal: take a tape measure and wrap it around your ankle, above the ankle bone, as that is where the strap will sit (see product imagery and fit video for a visual demonstration). This measurement is based on the last adjustment point on the strap.

Size Strap length will accommodate an ankle measurement up to the size below
5 23 cm
5.5 23 cm
6 23 cm
6.5 23 cm
7 24 cm
7.5 24 cm
8 24.5 cm
8.5 24.5 cm
9 24.5 cm
9.5 25 cm
10 25 cm
10.5 25.5 cm
11 26 cm
11.5 26 cm
12 26 cm

Belt Sizes

Natural Waist Measurement Typical Jean Size Belt Size for High‑rise Pant Belt Size for Mid‑rise Pant Infinite Belt Size
23-25" 23/24 26" 28" 1
25-26" 25 28" 30" 1
26-27" 26 30" 32" 1
27-28" 27 30" 32" 1
28-29" 28 32" 34" 2
29-30" 29 32" 34" 2
30-31" 30 34" 36" 2
31-32" 31 34" 36" 2
32-33" 32 36" 38" 3
33-34" 33 36" 38" 3
34-35" 34 38” 40" 3
36-37" 36 38" 40" 3
38-39" 38 40" 42" 4
40-41" 40 40" 42" 4
42-43" 42 44" 46" 4
43-44" 43 44" 46" 5
44-45" 44 46" - 5

Sizing Note: For the most accurate fit, measure around your body where you plan to wear the belt. Choose the closest belt size to that measurement.

Belt Diagram Accent Belt and Complement BeltThe Accent Belt, The Polished Belt and The Complement Belt size measurements start from the beginning of the leather to the middle hole.

Belt Diagram Infinite BeltThe Infinite Belt size measurements cover the entire length of the leather.

Belt Measuring Guide

Belt Measuring Guide

A - High-rise style:

If you plan to wear your belt around your natural waistline, wrap a measuring tape around the narrowest part of your midsection. Then, add 3” to determine your high-rise belt size.

B - Mid-rise style:

If you plan to wear your belt lower than your natural waistline, you will require a dierent size. If you have a particular pair of bottoms you intend to wear your belt with, wrap a measuring tape through the belt loops while in a relaxed position.

When wearing your belt in your preferred style, it should fasten in the middle hole. The belt will relax with wear allowing you to cinch it tighter, as needed.

If you plan to wear the belt in both the high and mid-rise styles, you have two options:

  1. Select your high-rise style and fasten it more loosely when worn in the mid-rise style.
  2. Select your mid-rise style and fasten it more tightly when worn in the high-rise style.