How to Style Winter Boots

As the weather transitions from fall to winter, it can be difficult to keep warm while still being fashionable. This winter season, riding boots, chunky heeled booties, combat boots, detailed black boots, and Chelsea boots are on trend to keep your toes toasty.
Boots Collage
Riding Boots
Classic riding boots are always in during the fall and winter season. They are a staple piece that are comfortable and stylish, while also providing extra warmth during those chilly days. Wear these boots on their own or with a pair of knee-high socks peaking out to add more detail to an outfit.
Sophomore, Melissa E., incorporates her riding boots in a casual but chic outfit. Her taupe boots add to the effortless look because of the light neutral color that go perfectly with the olive green utility jacket and white boho top.


Chunky Heeled Booties
Senior Dana Bredeweg styles brown Forever 21 boots with mostly denim outfit and a pop of yellow.
Chunky heeled boots automatically elevate any outfit. The flattering cut and slight heel elongates the legs and provides some height. They are a versatile piece that can easily transition into every season and be worn for any occasion. Chuck these shoes on with a pair of your favorite jeans for a sleek look that makes you seem a little more put together.
Chisa Cheong sports her tan boots with a pair of blue jeans and a comfy sweater underneath her peacoat. Showing a sliver of ankles gives a more polished look that complements the style of her outfit. These boots are a staple piece in her wardrobe that she typically wears with jeans and a chunky sweater.


Combat Boots
This military inspired footwear has been the ultimate laid back, grungy shoe for the fall and winter months. Although combat boots can be a hassle to lace up, they are the perfect shoe to put on because of the durability in the unpredictable winter weather. In addition, the masculine style of the boots can transform a plain outfit into an edgier look.


Senior, Noelle Nercessian has been obsessed with her Doc Martins for the past four months. She says, “I pretty much style my outfits around them. I wear a lot of black and I like to keep my outfits very minimal.” Here she rocks an effortless cozy look incorporating her neutral color palette, but spices up her outfit by throwing on her staple pair of combat boots to make the outfit a little edgier.
Detailed Black Boots
A simple pair of black boots is a Holy Grail item in many peoples’ closets, but wearing black boots that have small details are all the rage this year. Ankle cut outs, exposed heels, peep-toe cut outs, etc. have been commonly worn in street style as these details add a twist to the classic black boots. It is refreshing to see a staple item being revamped into a more intricate design that gives an element of surprise to an outfit.


Similar to Noelle’s outfit, Junior, Courtney Buck, puts an unexpected twist on a simple B&W outfit by wearing her cut out ankle boots. Although black is a basic color that goes with any outfit, the detail on the boots makes it a bit more challenging to style because the side cut out acts as a statement itself. So, Courtney usually wears black or white clothing pieces and black jeans to give a sleeker appearance to a typical college student outfit.
Chelsea Boots
Rock these boots during any season. They are the most transitional and versatile piece to have, especially as a college student. The Chelsea boots can be easily dressed up or down and match with any fashion style. They combine a utilitarian build with a sturdy framework, making it the perfect shoe for both males and females. Also, the flat surface of the shoe provides the utmost comfort suitable for walking to class or running errands.


David Vuong styles his brown Chelsea boots in a sporty, casual outfit. He wore a denim jacket layered over a hoodie and a basic white-T with dark pants and a baseball cap.
In contrast, Senior, Cheryl Wisdom, styles her Chelsea boots in a more classic, “Taylor Swift” look. She wore her olive parka over a black and white striped sweater paired with leggings and a grey beanie. To finish off the look, she wore her black patent leather Chelsea boots and added a pop of color with her red socks that peak out.
How are you styling your winter boots this season?
—> Tweet us a pic @DressedUpDucks
Words by Malia Ito, @maliaito
Photos by Elinor Manoogian-O’Dell, @ElinormODell

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