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Stylists share 10 shoes that are in style this winter and the best ways to wear them

Cheyenne Lentz   

Stylists share 10 shoes that are in style this winter — and the best ways to wear them
Stylists predict that slip-on and derby shoes will be popular this winter.Jeremy Moeller/Getty Images; Edward Berthelot/Getty Images
  • Insider asked stylists which shoes are trending this winter and the best ways to wear them.
  • Chunky combat boots and Chelsea boots can create a casual yet edgy look in any outfit.

Insider asked stylists which shoes they think will be popular this winter.

Here's what they had to say.

Sporting a pair of Western boots can add character to your look.

Sporting a pair of Western boots can add character to your look.
Western boots emulate a cool cowboy look.      MoMo Productions/Getty Images

According to Patrick Kenger, personal and celebrity stylist and image consultant at PIVOT, Western boots can be a fun way to add character to your look.

The stylist said Western-inspired boots often feature pointed toes and intricate stitching details and can be paired with jeans, a "cowboy-style" plaid shirt, and a leather jacket.

Combat boots are growing in popularity.

Combat boots are growing in popularity.
Combat boots look chunky yet chic.      alexandarilich/Getty Images

Alex Rivera, stylist and styling team manager at Stitch Fix, said chunky combat boots are gaining popularity this winter.

"For a street-wear-inspired look, I recommend pairing them with cargo pants, a graphic or band tee, and a bomber jacket to channel your inner rockstar," Rivera told Insider.

If going for a more edgy look, Kenger recommends an elevated combat boot with unique lacing.

Mary Janes are all the rage right now.

Mary Janes are all the rage right now.
Mary Janes can be styled in so many ways.      CaseyHillPhoto/Getty Images

Letam "Ley" Duson, founder of Ley All Day Personal Styling, told Insider that Mary Jane shoes are having a moment.

They come in a variety of styles, materials, and colors so there are countless ways to wear this classic shoe.

The stylist recommends pairing pointed-toe Mary Janes with a sweater and pleated skirt with tights or wearing the shoes with wide-leg pants and a lady jacket.

Loafers are trending as the "old money" aesthetic soars.

Loafers are trending as the "old money" aesthetic soars.
Loafers look classic and preppy.      Guerilla/Getty Images

As the preppy aesthetic continues to take off, Rivera told Insider that loafers are a great way to channel your inner Rory Gilmore.

Rivera said the shoes come in a variety of silhouettes, from shearling-lined to chunky styles, and can be paired with cuffed jeans and a simple knit sweater for "a cozy ensemble you can come back to all winter long."

Elevated sneakers are comfortable and still look sharp.

Elevated sneakers are comfortable and still look sharp.
Sneakers can be used to elevate a look or dress it down.      unomat/Getty Images

Elevated or platform sneakers come in a plethora of colors and materials.

Duson recommends pairing the sneakers with slim straight-leg jeans and a flannel button-down for an easy winter look that's sharp and comfortable.

For an edgier, sporty street-style look, Kenger would pair platform sneakers with jogger pants, a hoodie, and a long puffer vest.

Ballet flats are having a major moment.

Ballet flats are having a major moment.
Ballet flats can be worn on milder winter days.      Nevena1987/Getty Images

Rivera said it's no surprise that ballet flats have become all the rage alongside the rise of balletcore style inspired by ballerinas.

Ballet flats can provide comfort and practicality while keeping your look chic and on-trend on milder winter days.

"For everyday wear, style a neutral ballet flat with your favorite pair of jeans, a chunky sweater, and a blazer or long-line coat," Rivera told Insider.

If you're going for a dressier look, the stylist recommends pairing leather ballet flats with a maxi skirt or dress and a leather blazer or trench coat.

Chunky Chelsea boots are comfy and stylish.

Chunky Chelsea boots are comfy and stylish.
Chelsea boots can be rugged and chunky.      SHipskyy/Getty Images

If you're aiming for a more rugged look, Kenger recommends a chunky Chelsea boot.

"Chunky Chelsea boots have a thicker sole and often feature elastic side panels for added comfort," he told Insider.

Pair Chelsea boots with jeans and a sweater or turtleneck for a cozy, rustic style.

Knee-high boots can easily be dressed up or down.

Knee-high boots can easily be dressed up or down.
Knee-high boots are perfect for casual and fancier looks.      MoMo Productions/Getty Images

Rivera said knee-high boots are fun to style in the colder months.

The stylist recommends pairing them with a favorite slip dress, trench coat, and tights for a night out.

They can also be styled with a midi skirt and an oversized sweater for a more casual look.

Derby shoes are having a resurgence this season.

Derby shoes are having a resurgence this season.
Derby shoes are gaining popularity this winter.      Edward Berthelot/Getty Images

Derby shoes are having a resurgence this winter, especially when it comes to more laid-back outfits.

According to Rivera, derby shoes have been a classic choice for formal attire but can also work for more casual wear.

Pair derby shoes with dark-wash denim pants and a good-quality crewneck sweatshirt for a simple yet classy outfit.

Slip-on shoes and clogs will be a winter staple.

Slip-on shoes and clogs will be a winter staple.
Clogs are comfy and easy to slip on and off.      Jeremy Moeller/Getty Images

According to Rivera, slip-on shoes and clogs will be a popular staple for everyone this winter.

Kenger recommends a fleece-lined slip-on for comfort, warmth, and ease of wear.

"I love styling a slip-on shoe with loose-fitting jeans and a cardigan or knitwear for a laid-back look that can seamlessly take you from the couch to running errands," Kenger said.

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