How to Wear Your Chelsea Boots

What to Wear With Your Chelsea Boots

From soft supple suede to classic leather to new vegan alternative materials, Chelsea Boots are timelessly cool, comfortable and fashionable. These boots are extremely versatile and can be a great addition to almost any outfit.

This style is also unisex and popular with many styles across the gender spectrum. But now, you're probably wondering, “how, exactly, do I style these versatile boots?” Wonder no more: we're here to walk you through every stylistic option.

Feminine Flair

Traditionally, Chelsea Boots were designed as men's wear, but thanks to the Mod fashion era of the 1950’s and 1960’s, this style is just as popular among women today. And for good reason! Show off and elongate your legs by pairing white Chelsea Boots with a shorts skirt or top of knee length skort and denim jacket for a fun, flirty vibe. These boots are often thought of as being a Fall or Winter staple, but they're a great option for any time of year. You can even pair them with a sun dress or long maxi dress for a softer look.

Although Chelsea Boots are now considered appropriate for nearly every setting and fashion situation, they were originally designed as riding boots. You can use your outfit to pay homage to the origins of the Chelsea Boot by wearing a pair of brown suede Chelsea Boots with a denim skirt and your favorite flannel for a look that shows you're ready to go riding. If you're not keen on this down-home country-girl vibe, soften it up by going for a more cabincore look. You can do this by throwing a cozy, cable knit sweater on over your flannel, leaving the collar peaking out, and swap your skirt for leggings or jeans. Wear a pair of black, patent leather chunk-heeled Chelsea Boots with a delicate flowy skirt and frilled blouse. This contrast in styles is great for creating an ultra-chic and high-fashion vibe.

Make It Masculine

As mentioned before, this style of shoe is unisex, and the Chelsea Boot can be made to look ultra-feminine or very masculine depending on what you wear with it. This shoe is a favorite among both feminine and masculine crowds for this reason, among others.

For a men’s wear style, Chelsea Boots look great paired with straight-legged or slim-cut denim jeans and a classic sweater. Adding a Chelsea Boot to this outfit will instantly buoy this look from casual to chic. Take your outfit from lounging or errand-running to date night-ready just by switching your sneakers for Chelsea Boots. Pair your Chelsea Boots with a pair of chinos to really take your look to the next level of sophistication. Add a dapper wool coat in the winter months.

Professional and Office-Ready

Is the Chelsea Boot work appropriate? Absolutely. Wear your favorite style of Chelsea Boot with women’s khaki pants and a blazer for a smart, office-ready look. You could even wear these boots with tights and a sleek professional skirt. Adding a chic winter coat, the same color as your Chelsea Boots, is a great Winter look that's smart and professional.

These boots can also be worn seamlessly from office to happy hour. A great alternative to a classic high heeled shoe, wear your Chelsea Boots on your next date night to stay looking flirtatious and fun while keeping your feet warm and comfortable.

Masculine styles can also easily dress up the Chelsea Boot. This shoe style looks great with a men’s suit and tie, making it an ultra-professional option. It can also be worn with khakis and a button-up for a more business-casual look.

Your Comfiest Boots

Chelsea Boots are great casual wear because they're super comfortable and easy to take on and off. These boots are a great option for weekend wear or for daytime running errands. They can easily be taken from a walk in the park to a day at the museum and they are entirely appropriate for either setting.

Wear your Chelsea Boots with your favorite pair of jeans and a comfy hoodie for hanging out with friends or lounging around the house for a super comfortable style that stays fashionable. For your daytime weekend adventures, wear your Chelsea Boots with an oversized sweater and a pair of corduroy pants. Don’t forget to cuff your pants around the ankle to show off your boots. For a similar warm weather look, wear your Chelsea Boots with your comfiest skirt and a linen shirt.

The Chelsea Boot is versatile, timeless and classic. It can be worn in nearly any setting and is appropriate any time of the year. This boot is sure to become a staple in your wardrobe.


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