The diminutive footwear that is running rampant in fashion is sometimes hard to figure out. How to wear booties? They look so adorable, these boots that stop right at the ankle. Who doesn’t love anything tiny and sweet? And the bootie is like a baby version of your favorite to-the-knee boot.

But the question remains, how to wear booties? Does the hem of the pant need to cover the bootie? And if so, does it negate the fact that you are wearing such an on-trend piece? (If a bootie is covered, does it still count as fashion forward?) Can you wear them with dresses–even if you are over 30? We solve all your bootie befuddlement by sharing everything you need to know about how to wear booties, the must-have accessory of the season.

How to Wear Booties

Jean, yes? Genius!

The easiest way to wear a bootie is with jeans. Yes, you can wear them with a straight leg or boot cut denim and let the hem of the jean cover the boot. But these babies are meant to be shown off, not hidden under the hem.

Try your bootie with a skinny jean to give the footwear a bit more attention. The jean should never puddle or scrunch at the ankle. Instead, the hem should skim the top of the shank of the boot. Are your jeans too long? Roll them with a tiny cuff, leaving about a half-inch between the bottom of the jean and the top of the boot. The look feels intentional and plays well with the studied casual vibe that a bootie and jean evoke. If you have more than a few inches of denim to roll into a cuff, skip the bootie. You want a tiny, tight cuff, not a giant doughnut of fabric at the ankle.

How to Wear Booties

This photo tutorial pretty much says it all. A tiny cuff on your skinny jeans works to let your on-trend footwear shine. Image courtesy of babble.com

Trousers trend

Pairing a bootie with a trouser is modern and fresh, though not for the faint of heart. The trouser should be at the ankle or grazing the top of the boot, with the most modern pairing one involving a menswear-style trouser with a bootie that reads more city-refined than cowboy boot.

How to Wear Booties

A trouser, which stops right at the ankle bone, with a bootie that stops just below it. Perfection! Image courtesy of StyleBistro.com

Want to wear your booties with flat-front skinny pant or legging? Make sure you pair the pant with a longer jacket, tunic or sweater. Unlike a to-the-knee boot, which visually keeps the skinny pant/legging from reading as too revealing, the bootie needs a longer element to keep the silhouette in proportion.

How to Wear Booties

With skinny jeans and booties, be sure to layer with a longer top, like this white blouse. Image courtesy of Pinterest

How to Wear Booties

Another example of pairing leggings or skinny jeans with booties and a longer, flowy top. Image courtesy of fashionjackson.com

Dress to the nines

Nearly every fashion magazine and style blogger is pairing the bootie with dresses and skirts. But it still feels scary to lots of women. And no wonder, since the bootie is a bit shocking in comparison to a sleek pump. But that is exactly the point of the pairing. Fashion is constantly challenging the eye, and pairing a short boot with a skirt is modern. From a refined pencil skirt paired with a 1940s-influenced bootie, to a floaty dress and bootie that mixes feminine with edgy, booties and dresses proclaim that you want to have fun with fashion.

The easiest way to wear a bootie and skirt or dress? Look for a bootie that has a low-cut front on the ankle. If the bootie goes up to or covers your ankle bone, it is going to dramatically shorten your leg. Also opt for a nude-colored bootie versus a stark black to soften the look.

This bootie is ideal for everyday style. The low cut ankle will slim legs and the nude shade will soften the look. They're also available in black! Details here. Image: Nordstrom

This bootie is ideal for everyday style. The low cut ankle will slim legs and the nude shade will soften the look. They’re also available in black! Image: Nordstrom

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How to Wear Booties

Here is an example of a skirt paired with a brown/nude bootie. Image courtesy fashionsy.com.

And here are some nude booties, similar to the above photo, that we love.

A fun heeled bootie is a fashion-forward substitute for the classic pump. Here are two on-trend peep-toe options. We love the idea of opting for a soft blush that can work as either a neutral or a splash of color. These tan booties are $149.95 and the blush booties are $159.95. Images: Nordstrom

A fun heeled bootie is a fashion-forward substitute for the classic pump. Here are two on-trend peep-toe options. We love the idea of opting for a soft blush that can work as either a neutral or a splash of color. These tan booties are $149.95 and the blush booties are $128.95. Images: Nordstrom

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The holy grail of wearing booties with dresses and skirts? A monochromatic look, with booties, tights and skirt all in one color for a perfect, uninterrupted line. Pairing a black pencil skirt, black tights and black booties is utterly sophisticated.

How to Wear Booties

The holy grail of booties with tights: match skirt, tights and booties with the same color. Image courtesy of babble.com.

And here are some black booties, similar to the above photo, that we love.

Both of these booties are fantastic options for achieving that oh-so-chic monochromatic look. The heeled booties are $89.95 and the flat booties are $179.95. Images: Nordstrom

Both of these booties are fantastic options for achieving that oh-so-chic monochromatic look. The high heeled booties are $269.95 and the low heeled booties are $128.95. Images: Nordstrom

Best buys

Three great options when shopping for a bootie? A 1″ bootie in a casual, wear-with-everything style or the stacked-heel booties featured below, with a bit more height. Lastly, the elegant stiletto heel bootie, which is a hybrid of a sexy pump and boot, a style that is by far the easiest to wear with dresses. We’ve rounded up a few of our favorite options below.

Flat — 1″ Heeled Booties

Low heel or flat booties

Whether tall or short, a basic pair of tan, low-heel booties are essential for everyday wear this fall. The taller Vince boots are an investment at $375 and the Kork-Ease ankle booties are $189.95. Images: Nordstrom

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2 — 3″ Heeled Booties

Heeled booties

Heeled booties are definitely our shoe of choice, especially as temperatures begin to drop. The Frye brown leather ankle booties are $347.95, the versatile black leather booties are $149.95 and the neutral navy booties are only $67.20! Images: Nordstrom

Pumps

Pump booties

Turn that bootie heat level up a notch by opting for some sexy bootie pumps! The elegant black pumps on the left are $258.95 and the classic tan slide-on pumps are $99.95. Images: Nordstrom

2019 Trends

For those wanting to rock the current trends, white booties are at the top of every fashionista’s style list. There are several more accessible styles this year as opposed to when they were new on the scene in 2018. And don’t forget about the trend overtaking our summer and fall clothing — animal print. We’ve selected our favorites below that are still classic and wearable, while also being at the height of style this season.

White Booties

White booties are by far the trendiest shoe of the season. They’re edgy, yet elegant and you’ll feel like a total fashionista wearing them out on the town! The first pair on the left is made from vegan leather and are more affordable with an $88.95 price tag, the western booties in the middle are $159.95 and the last pair are from high-end designer Botkier for $227.95. Images: Nordstrom

Animal Print Booties

Animal print booties

Animal print booties are hot on the heels of the white booties this season. The stiletto pair on the left is $258.95, the grey snakeskin booties are $79.95 and the darker brown/black print booties are $224.95 — and our personal favorite.

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So who can wear the bootie? Anyone who can wear a regular boot. The shortened footwear darling is a perfect addition to your wardrobe if you want to add an element of modern style to your look. Follow a few simple rules, get over your footwear fears, and embrace the bootie trend.

For more “how-tos” check out more of StyleBlueprint’s fashion posts featuring tips and advice.