It’s officially fall, which means it’s time to cozy up, sip or eat something pumpkin-spiced and—of course—switch up your wardrobe. That includes your shoes too! While boots are clearly an autumn staple (we see you, knee-high and combat styles), there are so many different kinds to choose from. One of the most classic and versatile options? Chelsea boots. But since they’re not as tall as other popular styles, figuring out how to wear them can sometimes be a bit tricky. To help make it easier (and way more fun), we rounded up the seven best ways to style Chelsea boots.
Celebrity stylist Amanda Massi—who’s worked with stars like Kate Upton, Macy Gray and more—is ready to give some styling tips. That way, you can see some outfits these shoes look great with that you may have never considered before, and what kind of socks work best.
Browse through all the stylish, short boot looks below. And by the time you’re done, you’ll know how to style Chelsea boots, be ready to crunch some leaves in style and give your fall wardrobe the upgrade it deserves. From cozy casual outfits featuring leggings and jeans to dressier ones that are polished perfection, these ideas will have you feeling confident and comfy all season long. So, get ready, your boots are about to be the star of every look you wear!
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What Are Chelsea Boots?
If you’re not familiar with Chelsea boots, they are sleek, ankle-high boots known for their close fit and elastic side panels, which make them easy to slip on and off. Originally designed in the Victorian era by J. Sparkes-Hall, the bootmaker to Queen Victoria, they were later popularized in the 1960s. Their timeless, minimalist design makes them a versatile staple in anyone’s closet.
Related: These Are the Best Shoes To Wear With Dresses, According to Celebrity Stylists
What Not To Wear With Chelsea Boots
“In short, Chelsea boots are sleek, polished and refined, which is why they’re traditionally associated with smart casual or dressy looks,” Massi states. “Therefore, sweatpants shouldn’t be worn with Chelsea boots as they are inherently casual, sporty and relaxed.”
Even though athleisure looks are all the rage, and a lot of streetstyle looks will often dress up items like sweats, she doesn’t recommend going that route with Chelsea boots.
“The juxtaposition looks disjointed because the elegance of Chelsea boots conflicts with the lounge-wear vibe of sweatpants,” she says. “Sweatpants are also loose and baggy, which does not pair well with the slim, tapered silhouette of Chelsea boots; this breaks the balance. Chelsea boots require slim or straight trousers to maintain their sophisticated aesthetic, which sweatpants break completely.”
Massi notes that certain socks should also be avoided.
“Since Chelsea boots are sleek and fitted footwear with a clean neckline, bulky socks or brightly colored, thick socks can disrupt this line and make the outfit look heavier,” she says. “Because of those things, these should also be avoided when wearing Chelsea boots.”
What Socks To Wear With Chelsea Boots
When it comes to what types of socks you *should* wear with Chelsea boots, Massi suggests three different styles:
Thin or medium-weight dress socks
“These types of socks work preferably in neutral colors like black, navy or dark gray,” she states. “They are great because they create a sleek line that complements the clean silhouette of Chelsea boots.”
No-show or ankle socks
“For a casual look, this style of sock works best,” she notes. “They are especially good to pair with Chelsea boots in warmer months or with cropped pants that show the ankle, as no-show socks give a modern, minimalist vibe.”
Patterned or textured socks
“Thin patterned socks, like with subtle stripes or small dots, can add personality without overwhelming the boots or outfit,” she tells Parade.
How To Style Chelsea Boots—7 Best Ways To Wear Them, According to a Celebrity Stylist
1. Match your boots with your top
Not sure what to wear with your Chelsea boots? Massi says one idea is to consider your boots’ color when choosing your outfit, like in this example. That way, they coordinate.
“The black wool coat and black sweater paired with the rolled up jeans create a streamlined appearance, and I love that the black Chelsea boots match the formality and color palette perfectly, enhancing the outfit’s sophistication,” she reveals. “I also like how the Chelsea boots look sleek and polished with the sharp silhouette, and they complement the overall chic, tailored style.”
What would she change?
“To bring the look to the next level, I’d suggest adding a statement belt (perhaps a subtle metallic or designer belt) to cinch in the waist and add structure, or a luxury handbag for a polished finishing touch,” she suggests.
2. Channel streetwear chic
If you’re more into laidback outfits, Massi says this is one way you can rock Chelsea boots, sharing that a pair in a fun color or a metallic shade can be a fun addition.
“These silver Chelsea boots bring a tailored and edgy feel to an otherwise casual, oversized hoodie look,” she tells Parade. “Their shape contrasts stylishly with the loose garment and they elevate the hoodie, adding a fashionable edge and balance—anchoring the oversized silhouette on the lower half with cool minimalism.”
To make the look even more fashionable, Massi says she would switch the shorts to pants.
“I would consider adding leather leggings or skinny jeans underneath to emphasize leg shape and provide better contrast,” she says. “I would also layer minimalist jewelry, like gold chains or chunky rings, as they could amplify the chic streetwear vibe.”
3. Dress up your leggings by going monochromatic
When it comes to clothing that looks good with Chelsea boots, leggings are a go-to for many, and for good reason.
Massi explains that when an entire outfit is worn as a monochromatic look (including your footwear), it can elevate leggings even more, so they appear less casual than they would otherwise.
“This look is chic, and the boots complement it without being too flashy. Their sleek
style balances the layers and textures harmoniously in a casual yet stylish city outfit,” she notes. “If I were to incorporate something else, I would add a statement scarf or an oversized tote.”
Related: These Are the Best Shoes To Wear With Leggings, According to a Celebrity Stylist
4. Go glam
The best thing about Chelsea boots is that they can be found in a variety of shades, like gold, which makes them appear more high-fashion.
“Gold-colored Chelsea boots are a bold fashion statement—luxurious and eye-catching,” Massi explains. “This color can elevate any form of outerwear with a splash of glam, maintaining a high-fashion look that’s both cozy and luxe. The contrast between the black and gold in this outfit highlights the boots perfectly. Plus, it’s a great way to bring color into your outfit and allows you to make the boots a focal piece.”
The only thing she tells Parade she’d add are some accessories.
“I think adding subtle gold accessories, like earrings and bracelets, would harmonize the overall look with the boots,” she says. “I would also add a sleek black leather clutch for texture contrast and enhanced glam.”
5. Consider a seasonal look
Another idea is to dress for the season by including hues that go with that time of year.
“I like that the neutral brown beanie and the overall style of the outfit complement the boots, making a cohesive autumn-winter casual outfit that balances comfort with style,” Massi points out.
To accentuate the color of the boots even more, she reveals she’d bring in their tone elsewhere in the look too.
“I would add a tailored camel or beige coat for layering purposes and a slim scarf or statement gloves, which could bring in some texture and polish,” she states.
6. Plan for elegance
You can’t go wrong with a black and white look, which is why Massi says these black Chelsea boots help create a classic ensemble that has sleek styling.
“I like that the outfit feels refined, but it also makes a person seem approachable,” she explains. “I think including a luxury watch or structured blazer to refine the silhouette further would be nice, and if you wanted a pop of color, you could do so with a
handbag or scarf, which would add interest without overwhelming the overall outfit.”
7. Add some edge
This outfit shows that Chelsea boots can take on many different styles, including edgy when paired with things like a black leather trench coat, dark top and jeans.
“This look proves that Chelsea boots can look modern and be versatile,” Massi tells Parade. “I like that as part of this outfit, they balance the graphic nature of the cap and outerwear, grounding the look with a polished edge that isn’t overly formal. All it’s missing is a sleek crossbody bag or layered chain necklaces to juxtapose the urban wearable elements with
sophistication for a balanced street-luxe vibe.”
Up Next:
Related: 9 Best Ways To Style Loafers, According to a Celebrity Stylist
Source:
- Amanda Massi, celebrity stylist who has worked with talent such as Kate Upton and Macy Gray
