How to Style Your Chelsea Boots

First made popular by the Beatles, Chelsea boots are a practical yet polished option for every woman seeking for an effortless and edgy street style. With a sensible heel and elastic panels on the side, these boots are a must-have grab for last minute styling while its muted colors and materials never date, ensuring your feet stay fashion forward. Looking for inspiration on how to incorporate this boot into your street style? Keep in reading to scoop some of our styling tricks.

Classic Style

classic outfit with chelsea boots and orange fur scarf

classic outfit with gray coat and chelsea boots classic outfit with tweed blazer anf boots

The most timeless look of all fashion style, classic style is also the most elegant, streamlined, and sleek look you may go for if you wish to make your edgy footwear a bit chic. Like Kristina Bazan, keep your classic outfits sophisticated and feminine by topping it with a tweed blazer, and donning your elegant bag and a black pair of Chelsea boots. On the other way around, you can make your classic outfit a bit trendy by incorporating a brightly colored fur scarf like Kristina Bazan did, while sticking to your neutral pair of boots.

Borrowed-from-Boys Style

structured coat with sweater and chelsea boots tuxedo blazer with plain top and pointy boots tuxedo blazer with black blouse and ripped jeans

Due to its elastic side and pointy silhouette, Chelsea boots are perfect alternatives for your brogues, loafers, and oxfords that give a slightly masculine and edgy vibe complementing your borrowed-from-boys outfit. Tuxedo blazer, button-down shirt, and straight-leg pants are the common must-haves to wear the look, though you may go for ripped skinny jeans a black blouse to make your street style a bit unexpected and personalized like fashion blogger Masha Sedgwick did.

Retro and Vintage Style

animal print coat with chelsea boots vintage dress with trench coat and chelsea boots retro checkered dress with chelsea boots collared dress with chelsea boots

Trade your platform loafers and grungy combat boots with a pair of Chelsea boots that look a lot more polished and sleek without breaking your retro theme. Whether you wish for a black, brown, or gray pair, these boots will surely make your retro and vintage style look effortless with a bit of edge. Fashion blogger Jane Aldridge resorted to a retro floral print dress for her vintage style and topped with a trench coat. But her pair of gray Chelsea boots pulled the look together to an effortlessly cool look without forgoing her vintage theme.

Urban Street Style

chelsea boots with urban outfit urban outfit with chelsea boots turtleneck sweater with skinny pants and chelsea boots leather shorts with cropped leather jacket and edgy boots

If you’re a fan of leather jackets, moto vests, leather shorts, graphic tops, and denim jeans, Chelsea boots are perfect to complete your looks. Since you’ll be wearing denim jeans or black pants, keep the color contrast of your boots and pants low, therefore, making you look taller visually. A black pair of Chelsea boots with your black leggings or navy blue jeans will be great to look laid back and cool on your street style.

Modern Style

acid washed jeans with jacket and chelsea boots modern outfit with chelsea boots draped dress with burgundy chelsea boots camel outfit with gold chelsea boots brown outfit with white chelsea boots sleeveless jacket with striped top and skinny pants

Unconventional layers, eccentric structure, and architectural edges are some of the modern looks that can be complemented by a pair of Chelsea boots. Instead of going for a monochromatic look, you may think of getting a metallic gold or white pair of Chelsea boots to contrast with your neutral outfits making it look more modern and fashion-forward.

Simply Chic Style

lace dress with fedora hat and chelsea boots chic romper with chelsea boots black robe dress with gray chelsea boots

Looking for a simple but chic street style? Then go for shift dresses or rompers that look feminine without taking away the effortless vibe in you. You may also think of floral prints and pastel shades that look gentle and romantic since your pair of Chelsea boots will bring back the edgy vibe on your outfits.

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