How to Wear Jeans with Chelsea Boots

Co-authored by Susan Kim

Last Updated: October 20, 2020 References

Chelsea boots are slip-on ankle boots that are popular for both men and women. You can pair them with distressed jeans for a casual look, or dark wash jeans for a more formal occasion. Options abound for wearing jeans with your Chelsea boots! Pair your jeans with your boots based on color, and cuff or tuck them depending on the style of jeans.

Method 1

Method 1 of 2:

Choosing Jeans for Chelsea Boots

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Match your jeans’ color to your boots for a monochromatic look. Pair black jeans with black leather Chelsea boots for a sleek look. This style is especially popular with men, or anybody trying for a sleek, professional style.^{[1]
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- If you’re going for a professional style, wear a button-down collared shirt, or a nice blouse.
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Wear white jeans for a dramatic contrast. No matter the color of your Chelsea boots, wearing white jeans will really make them pop. White jeans are a popular summer style, but you can make them work in the winter too, with cute knitted sweaters, bright jackets, or even long coats.^{[2]
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Wear dark-wash jeans for more formal occasions. If you plan on wearing your jeans and Chelsea boots to a casual office, or out on a date, you might want to spiff up the look with dark wash jeans.^{[3]
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Expert Source

Susan Kim
Professional Stylist
Expert Interview. 30 April 2019.} Dark wash jeans look great with darker-colored Chelsea boots, in black or dark brown.^{[4]
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Wear light-wash or distressed jeans for casual occasions. Chelsea boots are great partly because they’re so versatile. They can look professional with your fancier jeans, and still look great with your light-wash and ripped-up jeans.^{[5]
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- Jean cut-offs look best with Chelsea boots when they’re cut off just a bit over the boot top.
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Pair brown suede Chelsea boots with blue jeans. Brown suede boots are more casual than black leather ones, and so will look great paired with ordinary, informal blue jeans. ^{[6]
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- You can pair this look with a tee-shirt, denim, flannel, or any other of your informal favorites.

Method 2

Method 2 of 2:

Styling Different Kinds of Jeans

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Cuff your straight jeans to expose a sliver of ankle. Roll the bottom of your jeans up 1 inch (2.5cm), and keep rolling until they are the right height to expose a little bit of your ankle. Having your ankle peek through will keep your ankles looking slim and show off your boots.^{[7]
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Half-cuff your skinny jeans for a casual look. If you’re going for a casual, weekend style, just fold the ends of your skinny jeans up once. Skinny jeans are often too tight to really roll them, so the half-cuff is a good solution. They will look perfectly imperfect and informal.^{[8]
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- Half-cuffing is great if you want to wear an informal top, like a tank top or a tee shirt.
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Tuck in your jeggings. If your jeans are a very thin denim, or are actually jeggings, you can tuck them into your Chelsea boots for a long, slim look. If your jeans are made of thick denim, don’t tuck them in, because they would get all bunched up and be uncomfortable.^{[9]
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- If you’re tucking your jeans in, consider wearing long socks pulled up over the boots, for a cute, wintry look.^{[10]
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Wear cropped jeans for an easy fix. Cropped jeans are particularly easy with Chelsea boots, because you don’t have to cuff or roll them at all. Cropped jeans have been making a comeback, and generally fall to just a bit above the height of your Chelsea boots. ^{[11]
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- Wide-legged cropped jeans will give you a dramatic flair.^{[12]
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- Skinny cropped jeans can look cute and casual.^{[13]
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Let your bootcut jeans fall over the tops of the boots. Bootcut jeans are a no-fuss option for wearing Chelsea boots. Just let the bottom of the jeans cover up the tops of your boots.^{[14]
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