The Best Ways To Style That Perfect Pair Of Booties

The Best Ways To Style That Perfect Pair Of Booties

Viktoria Minkova/Shutterstock By Maria Kieval/Oct. 11, 2022 9:50 pm EST

When booties hit the fashion scene about a decade ago, no one really knew how to style them. Even so, you knew you had to have them. They felt downright modern and practical because you could wear them with any type of pants, dresses, or skirts. The average 2010 girl could be seen wearing ankle-grazing booties with skin-tight skinny jeans and a flowy top or with the of-the-moment body-con mini skirts and dresses. You may have felt cute at the time, but looking back, you may have done things differently.

According to Vogue, a bootie is defined by its “shorter stature, usually hitting around the ankle, just above or below.” They can range in height from modest heels and flats to sky-high stilettos. Boots, by contrast, are designed to sit higher on the leg, ranging from mid-calf to over the knee. Some booties are cut loose, while others hug like a sock and can be heeled or flat. The practicality of booties still stands true today. But one major thing has changed: we now have more insight into how to style them. Whether you still have your classic leather pair from years ago or just snagged a new pair for fall, we’ve researched and compiled the best (and most current) ways to wear your favorite pair of booties.

Instead of skinny jeans, try straight leg denim

Melodie Jeng/Getty Images

There’s no doubt that your perfect pair of booties look best with denim, but the skin-tight jeggings of the past won’t do. At this point, they just feel too constricting. Opt instead for a straight-legged pair that crop at the ankle, stopping at the edge of the boot or extending over an inch or two, per An Indigo Day. A nice block-heeled bootie (pictured above) is perfect for every day. You can wear them with frayed jeans or a trendy cropped bootcut style anywhere from date night to coffee and shopping with friends.

There’s also the option of sleek sock booties, which tend to look a bit more polished and fit nicely under denim or trousers. A pair of these are the ideal choice for the office or even a more formal occasion, per Ego Shoes. Sock booties can either look retro or completely modern, but either way, they will add fashion cred to any outfit. We love the beautiful Louie Stretch Sock Bootie by Reformation for the perfect heel height and updated square toe.

Pair edgy boots with a feminine midi-skirt

Sabelnikova Olga/Shutterstock

Midi-length skirts have become a closet staple over the last few years. They are clearly more of a conservative look, especially considering the midi’s 1940’s origin, says College Fashion. But today’s fashionistas aren’t wearing Mary Janes with their modest midi skirts. Instead, they counteract the classic silhouette with sporty white sneakers or edgy ankle booties, says Fashion & Mash.

We love a pointed-toe cowboy boot (like the ones pictured above), especially paired with an ultra-feminine midi skirt. The sharp edges of a western boot coupled with the softness of a midi skirt is an unexpected contrast, but it works. Let’s not forget the chunky lugged sole booties or lace-up style boots that have been everywhere as of late. The trendy style looks casually chic when worn with jeans and black leggings, but why not have a bit more fun with it? Try out a play on opposites by wearing chunky ankle boots with girly dresses or a vintage midi skirt, which PopSugar calls “sassy but sweet.” We have to admit this may be one of our favorite ways to style ankle booties.

Balance proportions with a flowy skirt

Daniel Zuchnik/Getty Images

Sleek, low-profile ankle booties look great peeking out from a flowy maxi dress or even a mid-calf midi skirt. Just make sure the boots have a bit of a heel. “The best ankle boots with dresses are the ones that show off the boots while keeping the silhouette of your outfit balanced,” explains style blogger Emma Irene Cavanagh. “A long maxi dress with flats can often feel a bit frumpy so a medium heel works really well.”

Retro kitten-heeled booties look great with denim but also feel incredibly modern when paired with a feminine dress or skirt, says Vogue. The minimal silhouette elongates the legs, is easy to walk in, and amps up the feminine aesthetic. As you can see, there are several new and exciting ways to style your favorite pair of booties. From chunky lace-ups to sleek block-heeled and sock styles, there’s no doubt you have a stylish outfit already waiting for you in your closet.

The Best Ways To Style That Perfect Pair Of Booties

Viktoria Minkova/Shutterstock

By Maria Kieval/Oct. 11, 2022 9:50 pm EST

When booties hit the fashion scene about a decade ago, no one really knew how to style them. Even so, you knew you had to have them. They felt downright modern and practical because you could wear them with any type of pants, dresses, or skirts. The average 2010 girl could be seen wearing ankle-grazing booties with skin-tight skinny jeans and a flowy top or with the of-the-moment body-con mini skirts and dresses. You may have felt cute at the time, but looking back, you may have done things differently.

According to Vogue, a bootie is defined by its “shorter stature, usually hitting around the ankle, just above or below.” They can range in height from modest heels and flats to sky-high stilettos. Boots, by contrast, are designed to sit higher on the leg, ranging from mid-calf to over the knee. Some booties are cut loose, while others hug like a sock and can be heeled or flat. The practicality of booties still stands true today. But one major thing has changed: we now have more insight into how to style them. Whether you still have your classic leather pair from years ago or just snagged a new pair for fall, we’ve researched and compiled the best (and most current) ways to wear your favorite pair of booties.

According to Vogue, a bootie is defined by its “shorter stature, usually hitting around the ankle, just above or below.” They can range in height from modest heels and flats to sky-high stilettos. Boots, by contrast, are designed to sit higher on the leg, ranging from mid-calf to over the knee. Some booties are cut loose, while others hug like a sock and can be heeled or flat.

The practicality of booties still stands true today. But one major thing has changed: we now have more insight into how to style them. Whether you still have your classic leather pair from years ago or just snagged a new pair for fall, we’ve researched and compiled the best (and most current) ways to wear your favorite pair of booties.

Instead of skinny jeans, try straight leg denim

Melodie Jeng/Getty Images

There’s no doubt that your perfect pair of booties look best with denim, but the skin-tight jeggings of the past won’t do. At this point, they just feel too constricting. Opt instead for a straight-legged pair that crop at the ankle, stopping at the edge of the boot or extending over an inch or two, per An Indigo Day. A nice block-heeled bootie (pictured above) is perfect for every day. You can wear them with frayed jeans or a trendy cropped bootcut style anywhere from date night to coffee and shopping with friends.

There’s also the option of sleek sock booties, which tend to look a bit more polished and fit nicely under denim or trousers. A pair of these are the ideal choice for the office or even a more formal occasion, per Ego Shoes. Sock booties can either look retro or completely modern, but either way, they will add fashion cred to any outfit. We love the beautiful Louie Stretch Sock Bootie by Reformation for the perfect heel height and updated square toe.

There’s also the option of sleek sock booties, which tend to look a bit more polished and fit nicely under denim or trousers. A pair of these are the ideal choice for the office or even a more formal occasion, per Ego Shoes. Sock booties can either look retro or completely modern, but either way, they will add fashion cred to any outfit. We love the beautiful Louie Stretch Sock Bootie by Reformation for the perfect heel height and updated square toe.

Pair edgy boots with a feminine midi-skirt

Sabelnikova Olga/Shutterstock

Midi-length skirts have become a closet staple over the last few years. They are clearly more of a conservative look, especially considering the midi’s 1940’s origin, says College Fashion. But today’s fashionistas aren’t wearing Mary Janes with their modest midi skirts. Instead, they counteract the classic silhouette with sporty white sneakers or edgy ankle booties, says Fashion & Mash.

We love a pointed-toe cowboy boot (like the ones pictured above), especially paired with an ultra-feminine midi skirt. The sharp edges of a western boot coupled with the softness of a midi skirt is an unexpected contrast, but it works. Let’s not forget the chunky lugged sole booties or lace-up style boots that have been everywhere as of late. The trendy style looks casually chic when worn with jeans and black leggings, but why not have a bit more fun with it? Try out a play on opposites by wearing chunky ankle boots with girly dresses or a vintage midi skirt, which PopSugar calls “sassy but sweet.” We have to admit this may be one of our favorite ways to style ankle booties.

We love a pointed-toe cowboy boot (like the ones pictured above), especially paired with an ultra-feminine midi skirt. The sharp edges of a western boot coupled with the softness of a midi skirt is an unexpected contrast, but it works.

Let’s not forget the chunky lugged sole booties or lace-up style boots that have been everywhere as of late. The trendy style looks casually chic when worn with jeans and black leggings, but why not have a bit more fun with it? Try out a play on opposites by wearing chunky ankle boots with girly dresses or a vintage midi skirt, which PopSugar calls “sassy but sweet.” We have to admit this may be one of our favorite ways to style ankle booties.

Balance proportions with a flowy skirt

Daniel Zuchnik/Getty Images

Sleek, low-profile ankle booties look great peeking out from a flowy maxi dress or even a mid-calf midi skirt. Just make sure the boots have a bit of a heel. “The best ankle boots with dresses are the ones that show off the boots while keeping the silhouette of your outfit balanced,” explains style blogger Emma Irene Cavanagh. “A long maxi dress with flats can often feel a bit frumpy so a medium heel works really well.”

Retro kitten-heeled booties look great with denim but also feel incredibly modern when paired with a feminine dress or skirt, says Vogue. The minimal silhouette elongates the legs, is easy to walk in, and amps up the feminine aesthetic. As you can see, there are several new and exciting ways to style your favorite pair of booties. From chunky lace-ups to sleek block-heeled and sock styles, there’s no doubt you have a stylish outfit already waiting for you in your closet.

Retro kitten-heeled booties look great with denim but also feel incredibly modern when paired with a feminine dress or skirt, says Vogue. The minimal silhouette elongates the legs, is easy to walk in, and amps up the feminine aesthetic.

As you can see, there are several new and exciting ways to style your favorite pair of booties. From chunky lace-ups to sleek block-heeled and sock styles, there’s no doubt you have a stylish outfit already waiting for you in your closet.