How to Match Any Outfit With a Chelsea Boot

What Is the Chelsea Boot? 

Chelsea boots are a style that has endured, relativity unchanged since the Victorian era. Chelsea are usually leather, close fitting, ankle high boots and feature an elastic panel on the side. Chelsea boots are almost flat, with just a slightly raised heel. This easy-on, easy-off style typically has a loop at the back of the ankle that can be used to pull the boot on. Chelsea boots are easy to style and comfortable to wear. Best of all, Chelsea boots work year-round, though they usually get the most wear in the fall and winter. 

How to Tie Together Any Outfit With a Chelsea Boot

Wear Chelsea Boots With Cropped Jeans

When you have adorable boots, you absolutely want to show them off. Forget shoving your boots under pants! Let them shine by pairing your Chelsea boots with cropped jeans. The look works best with cropped jeans with a slight flair, especially if the jeans have an on-trend raw edge. Look for cropped jeans that hit just one to two inches above the top of your boots, so that you are showing the perfect amount of leg. 

Wear Chelsea Boots With Full-Length Jeans

Is there anything better than a pair of jeans, some great boots, and a cute top? It is an outfit formula that is easy to dress up or down, and you can mix and match for endless looks. For properly pairing full-length jeans with Chelsea boots, Bright on the Day has a few options. First, if you are wearing closely fitted skinny jeans, you can simply tuck your pants into your jeans. This is an easy way to elongate your leg and make you look taller. For a slightly more stylish look, that also works with jeans that are not skintight, roll the hem of your jeans under. Tuck the hem of your jeans under themselves until they hit just above the top of your boots, for a bit of peek-a-boo skin. The third option is slightly more casual and is an instant way to elevate a basic outfit to an on-trend look. Just roll up the hem of your jeans until they are one to two finger widths above the top of your boots. This look is at its best with dark wash jeans when there is some color contrast between the inside and the outside of your jeans.

Wear Chelsea Boots With Ripped Jeans

Ripped skinny jeans, with gaping holes at the knees or thighs are an off-the-moment look that pairs perfectly with Chelsea boots. Top off a casual look with a wide brim felt hat and a plaid or checked shirt unbuttoned over a solid tank top. To elevate the look, switch out the plaid top for a well-cut blazer. 

Wear Chelsea Boots With a Long, Floral Dress

Floral, flowing maxi dresses are fun and feminine. We usually think of wearing them with sandals, flats, or heels. But do not overlook the power of a Chelsea boot with a long dress. Sometimes, the traditional options are a little too girly or formal, especially in the fall and winter months. Popping on a Chelsea boot toughens up the look and gives your dress a bit more of a casual feel. For a little extra edginess, top the outfit with a leather moto jacket to balance out the look.

Wear Chelsea Boots With Short Skirts

Like pairing your boots with a floral dress, wearing Chelsea boots with a short skirt is fun way to create a youthful vibe. This is also an excellent way to make summer skirts work well into the fall and winter. For a bit of warmth, add tights with a subtle pattern, such sheer black tights with polka dots. If you prefer bare legs, opt for Chelsea boots in rust or a light brown shade, since a dark color could make the outfit look bottom heavy. 

Wear Chelsea Boots With a Structured Dress

Who says you need to wear teeter around the office in toe-squishing stilettos? A fitted structured dress might be your favorite piece of workwear, but the traditional shoe choice is both uncomfortable and too predictable. Set the heels aside and step into a pair of Chelsea boots. Then, balance the look by adding a boyfriend-style blazer in a check or plaid print.  

Wear Chelsea Boots With a Pencil Skirt

Like a structured dress, a pencil skirt is a workday staple. To freshen up the look, pair a pencil skirt, which hits just below the knee, with a pair of Chelsea boots in a coordinating shade. Then, create balance and add some drama to the top of your outfit with a chunky knit sweater or an open-front cardigan. 

Wear Chelsea Boots With Leggings

Soft, stretchy leggings are the coziest, most comfortable pieces of clothing in your closet. Sadly, it is hard to style leggings for places other than the gym or your home office. But good news!  A great pair of Chelsea boots can help you kick your legging looks up a notch. Toss on an oversized sweater over figure-hugging leggings, add a large tote, a few pieces of delicate jewelry and your Chelsea boots. Suddenly, your favorite leggings are ready for everything from a travel day to running errands to meeting friends for a casual lunch. The look gets even more stylish when you swap out your usually leggings for a pair in faux leather or a pair in a moto style with leather insets.

The Best Chelsea Boots for Any Outfit

For top-quality Chelsea boots for women that are a perfect mix of cute and comfy, check out De Wulf. Their boots come in a variety of shades, including dark blue, rust, coffee and black. De Wulf Chelsea boots are a classic look that are ready for help you create loads of new outfits.

Vivianne Sterling

Editorial Manager at Beautips. I love street style and I'm always in search of bits of inspiration around me. I also believe in home-made solutions for fitness, beauty tricks and healthy cooking.

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