Your Guide To Styling Classic Chelsea Boots

With the cold weather approaching, you may already be planning all of your cozy and chic layered looks. And what is a good fall or winter outfit without a stylish boot to complete it? Timeless Chelsea boots may already be in your closet, and if they aren't, you may just need to go shopping after seeing how they can elevate your look. Queen Victoria is often credited with having been the owner of the first Chelsea boot to ever be invented in 1837, according to The Powerhouse Museum.They have only improved since then and have never really gone out of style, a sign of classic footwear.

Chelsea boots are known for being made of leather or suede and having a panel of elastic fabric on each side which makes the process of putting them on and taking them off easier (via Oliver Cabell). They come in a variety of heel styles such as the block heel, the platform sole, and the lug sole with indentations, and can be dressed up or down. Their androgynous nature makes them a perfect option for anyone looking to elevate their look. Here are our favorite ways to style them this fall.

With a skirt and tights

For an easy fall transition outfit that is equal parts flirty and cool, wear your Chelsea boots with either a casual skirt or one that is more dressed up. Complete the look with a pair of tights, a popular accessory during the colder months, especially if they are fleece-lined.

Celebrity stylist and costume designer Alexandra Imgruth tells Marie Claire that this combination is very mod-inspired. "I mainly wear my Chelsea boots with sheer black tights and a mini skirt or mini dress," Imgruth says. "Pairing the boots with a skirt or dress makes them easy to transition from day to night, and the short length gives a mod, '60s feeling."

With a midi dress

Wearing a midi dress is a cute way to show off Chelsea boots. The midi length hits about mid-calf, leaving enough room to display all the classic features of the Chelsea boot. Whether you choose a more form-fitted bodycon-style sweater dress or a flowy prairie-style dress, as seen on Merrick's Art, the boots will be the standout statement of your outfit. Dress them up or down and even get a bit playful and sport a cute pair of tube socks with them.

With edgy streetwear

Add an edgy vibe to your Chelsea boots by pairing them with streetwear. Think hoodies, nylon straps, baggy pants, and leather. Layering is key to this look, as are lots of bold colors. The final touch is a chunky Chelsea boot with a lug platform sole. "Chunky, platform boots are my favorite because they make me more confident than any other shoe," style writer Tara Gonzalez tells Refinery29. "If I feel like my outfit needs a little extra something, a platform boot instantly adds edge."

With a blazer

The Chelsea boot is sometimes referred to as the "Beatles boot" because the British musical quartet often wore them paired with suits, including for their famous Abbey Road photo, according to Oliver Cabell. Take a cue from the greatest rock band of all time and wear your favorite Chelsea boots to work. You won't sacrifice any professionalism if you pair them with a structured blazer. With a low, block-heeled Chelsea boot and a skirt or pantsuit, you'll look pulled together and chic.

With simple jeans

For the ultimate comfort, pair your Chelsea boots with classic jeans. This simple way of styling allows you to play around with the kind of top you wear. Choose from a long-sleeve blouse or a plain white t-shirt, a crop top with a puff sleeve accent, or a loose sweater. You can even ditch the denim and try a pant in a different material. The key is to be casual and comfortable to allow your Chelsea boot to be the star of the outfit.