Love Booties? The Dos and Don’ts of Wearing Ankle Boots

1,252 products
Maison Margiela Four Stitch Soft Touch Ankle Boots

Maison Margiela Four Stitch Soft Touch Ankle Boots

$995.00
Aquazzura Saint Honore' Booties 50

Aquazzura Saint Honore' Booties 50

$875.00
Loeffler Randall Cynthia Mid Heel Ankle Boots

Loeffler Randall Cynthia Mid Heel Ankle Boots

$395.00
Acne Studios Jensen Suede Booties

Acne Studios Jensen Suede Booties

$539.00
Alexandre Birman 85mm Evelyn Snow Booties

Alexandre Birman 85mm Evelyn Snow Booties

$895.00
Isabel Marant Dusta Boots

Isabel Marant Dusta Boots

$595.00
Freda Salvador The Ace Lace Up Booties

Freda Salvador The Ace Lace Up Booties

$495.00
3.1 Phillip Lim Alexa 40mm Boots

3.1 Phillip Lim Alexa 40mm Boots

$525.00
3.1 Phillip Lim Alexa 25mm Loafer Boots

3.1 Phillip Lim Alexa 25mm Loafer Boots

$495.00
Sam Edelman Hilty Booties -70%

Sam Edelman Hilty Booties

$180 $54.00
Ankle Boots Dos and Don'ts So You Style You Style Your Booties Correctly

About Booties Boots

The fashion world is obsessed with booties. Edgy and trendy, ankle boots offer an abundance of options from classic leather granny boots to heavily embellished suede and patterned boots. Booties are everywhere! And if you don’t have a handful of bootie options in your shoe closet, it’s time to catch up.If you have a pair of ankle boots collecting dust because you can’t figure out what to wear with them, it’s time to dust them off and start planning outfits. The short height associated with booties can make them difficult to pair successfully with bottoms. A good rule of thumb is to choose a closely fitted skinny or straight-leg jean that ends right at the top of your boot. Ankle cut jeans are ideal for this.But there are more ways to wear them. Take a look at the following dos and don’ts of ankle boots:
Read More

The fashion world is obsessed with booties. Edgy and trendy, ankle boots offer an abundance of options from classic leather granny boots to heavily embellished suede and patterned boots. Booties are everywhere! And if you don’t have a handful of bootie options in your shoe closet, it’s time to catch up.

If you have a pair of ankle boots collecting dust because you can’t figure out what to wear with them, it’s time to dust them off and start planning outfits. The short height associated with booties can make them difficult to pair successfully with bottoms. A good rule of thumb is to choose a closely fitted skinny or straight-leg jean that ends right at the top of your boot. Ankle cut jeans are ideal for this.

But there are more ways to wear them. Take a look at the following dos and don’ts of ankle boots:

Cuffed Jeans

If your jeans are a little too long or not as closely fitted as you like, you can cuff them. There are three main styles of cuffs:

  • 1-inch cuff – To create the 1-inch cuff, simply turn the bottom of your skinny jeans up one turn. Do use this cuff if you’re wearing short leather booties no taller than your ankle. Do allow a little bit of skin to show between the cuff and boot. Do not let the cuffs tuck into your boots.
  • 3-inch cuff – This cuff is similar to the one above. Simply turn your jeans up one turn. Do use this cuff if your skinny jeans are a bit too long. Do not use this cuff if you have short legs, as it can make your legs look even shorter.
  • Rolled cuff – Create a rolled cuff by pegging the legs of your jeans and turning them up two times to create a 1-inch cuff. Do use this option if your jeans are too long or loose at your ankles. Do not use this cuff if it shows too much skin.

R13 Boy Skinny Jeans with Cuffs

R13 Boy Skinny Jeans with Cuffs

$365.00
DSQUARED2 JEANS WITH ZIPPED CUFFS 36 Blue Denim -40%

DSQUARED2 JEANS WITH ZIPPED CUFFS 36 Blue Denim

$563 $337.80
Style & Co Curvy Cuffed Capri Jeans, Created for Macy's

Style & Co Curvy Cuffed Capri Jeans, Created for Macy's

$39.50
Kut From The Kloth Catherine Boyfriend Cuffed Jeans

Kut From The Kloth Catherine Boyfriend Cuffed Jeans

$89.00
Style & Co Curvy-Fit Cuffed Boyfriend Jeans, Created for Macy's -25%

Style & Co Curvy-Fit Cuffed Boyfriend Jeans, Created for Macy's

$49 $36.75
Zaful Grunge Light Wash Ripped Cuffed Boyfriend Jeans

Zaful Grunge Light Wash Ripped Cuffed Boyfriend Jeans

$28.49
Style & Co High Cuffed Capri Jeans, Created for Macy's -49%

Style & Co High Cuffed Capri Jeans, Created for Macy's

$39 $19.99
Lucky Brand Sweet Crop Cuffed Jeans -60%

Lucky Brand Sweet Crop Cuffed Jeans

$79 $31.73
GUESS Women's 1981 Cuffed High-Rise Jeans

GUESS Women's 1981 Cuffed High-Rise Jeans

$68.60
Flying Monkey Mid Rise Cuffed Skinny Ankle Jeans

Flying Monkey Mid Rise Cuffed Skinny Ankle Jeans

$84.00
Kut From The Kloth Cameron Cuffed Straight-Leg Ankle Jeans

Kut From The Kloth Cameron Cuffed Straight-Leg Ankle Jeans

$89.00

Cropped Pants

Cropped pants can work well with booties, especially taller ankle boots. If you choose to wear cropped distressed jeans or a shorter legging, make sure your boots are the appropriate height. Do show about 1 inch of skin. Do not show too much skin or allow your pants to come down over your boots.

Tucked Legs

It is usually not advisable to tuck pants into ankle boots, but it can work with the right bottoms. Only tuck leggings or skinny jeans that fit tightly against your leg. The legs of your pants should tuck perfectly and seamlessly. Do not tuck the legs of your pants into your ankle boots if it causes them to bunch or push up around your leg.

Skirt Considerations

Ankle boots are perfect for long, flowing skirts and miniskirts alike. However, you have to be careful with shorter and tighter skirts. The key is to not show too much skin. Do wear tights or thigh-high socks with miniskirts and booties. Do not wear booties with long, form-fitting skirts.

Once you learn how to wear booties, you will become obsessed with them. Low-cut, mid-cut, printed, embossed, embellished … there are so many reasons to love booties!

Madewell The Carina Block Heel Booties

Madewell The Carina Block Heel Booties

$188.00
Frye Veronica Shearling Booties

Frye Veronica Shearling Booties

$398.00
Loeffler Randall Kali Western Heeled Booties -80%

Loeffler Randall Kali Western Heeled Booties

$450 $90.00
Maison Margiela Tabi Faux Leather Sock Booties

Maison Margiela Tabi Faux Leather Sock Booties

$895.00
Create your personalized shopping feed - never miss what you'll love

Create your personalized shopping feed - never miss what you'll love

Sam Edelman Abella Booties -70%

Sam Edelman Abella Booties

$180 $54.00
RE/DONE Short Cavalry Boots

RE/DONE Short Cavalry Boots

$850.00
Isabel Marant Dicker Booties

Isabel Marant Dicker Booties

$560.00
Rag & Bone Razor Booties

Rag & Bone Razor Booties

$495.00
Aquazzura 85mm Boogie Booties

Aquazzura 85mm Boogie Booties

$825.00
Nicholas Kirkwood 70mm Lexi Ankle Boots

Nicholas Kirkwood 70mm Lexi Ankle Boots

$895.00
Alexander Wang Kori Stretch Booties

Alexander Wang Kori Stretch Booties

$595.00
Jeffrey Campbell Cloudy Rain Booties

Jeffrey Campbell Cloudy Rain Booties

$65.00
Filter
  1. Style 0

  2. Brand 0

  3. Size 0

  4. Price 0

  5. Color 0

  6. Closures 0

  7. Details 0

  8. Heel Height 0

  9. Heel Style 0

  10. Material 0

  11. Pattern 0

  12. Toe Style 0

  13. Availability 0