Chelsea boots have been a fashion favorite for what feels like forever, with different brands putting their own spin on them, from sleek platforms to the chunky lugged soles we’re seeing everywhere now. They are a timeless go-to because they’re just so comfortable and versatile.
But why are we focusing on them over other styles? Because I am a huge believer in comfortable fashion. For me, feeling good is just as important as looking chic and on-trend.
So let’s get into some of my favorite ways to work this ridiculously comfy and cool shoe into your everyday looks.
1. Get sporty with Shorts and Vitello Chelsea Boots
I love the idea of giving your look a little bit of an edge by pairing denim shorts with a simple tee or a half-tucked shirt and your Chelsea boots. It’s such a great way to create a new kind of grunge fashion.
You could also go for a more balanced look with some leather shorts and a tank. I’ve even seen colorful tailored shorts that look amazing with a cute top or blouse and a pair of Chelsea boots.
The girls in the images below are giving me so much inspiration!
Image: Pinterest @jess.
Image: Pinterest
2. The Classic Combination with Vitello Matt Chelsea Boots
Image: Pinterest @Linda Greene
For a look that is absolutely timeless, try styling your mid-calf Chelsea boots with a plain tee and some slim-fit jeans. This is such a classic combo. For fall and winter, you can just add a sweater.
And if you want to make it feel a little more elegant and classy, throwing on an overcoat or a leather jacket keeps the whole look minimal but with a seriously chic touch. The girl below has absolutely nailed this vibe.
3. Stay Relaxed with Sweatpants and Vitello Nature Chelsea Boots
Image: Pinterest @Ashley Mercedes
Image: Pinterest @LADYSVIBESS
Sweatpants and Chelsea boots are the perfect duo for keeping your look minimal and relaxed. To give off a confident vibe, pair your sweatpants that have an elastic hem with some tall Chelsea boots.
For cropped sweatpants with a wider hem, low Chelsea boots are the way to go.
The key is to keep the rest of your outfit simple so the boots can really be the star. A bodysuit, a simple tee, a crop top, or a matching sweatshirt on top all work perfectly. You can even layer the whole look with an overcoat.
4. Go Monochrome with Vitello Low Chelsea Boots
Image: @hairstylesbeauty.tumblr.com
You can create an equally chic and minimalist look by going for a monochrome outfit, just like the girl below. Pair your black Chelsea boots with black jeans and a black shirt. For winter, you can easily layer it with a jacket.
To finish off the look, just add a sling bag, and you’re all set for any outing or even a travel day.
5. Add a Pop of Color with Vitello Lilac Chelsea Boots
Image: @stylist.co.uk
Inject a little color into your wardrobe when you’re putting together chic looks with Chelsea boots. Whether it’s a shirt, a tee, a top, or a skirt, grab a bright and bold piece of clothing for your outfit of the day and finish it off with your favorite comfy and versatile Chelsea boots.
This is such a fun way to add some excitement to your outfit while keeping the whole look fresh and elegant.
6. Get Playful with a Short Skirt and Vitello Fuchsia Chelsea Boots
Image: Pinterest
From maxi to midi and mini, Chelsea boots are honestly perfect to style with any kind of skirt. A short leather skirt looks amazing with leather Chelsea boots and a tucked-in top.
If you want a standout chic look, just throw a jacket over it. For fall and winter, you could even add some fishnet stockings or tights.
You can also lean into that schoolgirl aesthetic with a pleated short skirt, a tee, and your go-to Chelsea boots.
Image: Pinterest
7. Check the Laid-Back Vibe with Baggy Jeans and Vitello Chelsea Boots
If you’re going for some laid-back vibes, try pairing your Chelsea boots with baggy jeans. The trick is to keep the whole look coordinated with silhouettes that are perfectly balanced.
With baggy jeans, a crop top or a bodysuit top creates a really well-balanced outfit. I also love the idea of layering the look with a leather jacket, just like the girl below.
8. Rock an Easy Look with Leggings and Vitello Matt Low Chelsea Boots
Image: Pinterest @pumpsandpushups.com
Image: Pinterest @merricksart.com
Leggings with Chelsea boots are a dream combination for any busy woman. When you’re on the move, you can just slip on your leggings with a tee, a tank top, or a sweatshirt and your favorite Chelsea boots, and you are ready to go.
To get a more sophisticated look, layer the tee with a shacket. You can also wear the shacket buttoned-down with your leggings.
Feel free to go for any type of leggings you love, from printed to leather, to create looks that are both playful and chic. The girls below are the perfect inspiration.
9. Go Bold with Prints and Vitello Fango Chelsea Boots
Image: Pinterest
For a bold and contemporary look, don’t be afraid to experiment with prints. Just pair your Chelsea Boots with anything printed, and you’re instantly ready to create a look that’s a mix of street style and runway fashion.
Take some inspiration from the girl below. In this look, she not only combines prints with her Chelsea boots but also keeps it so classy in a pantsuit. This is major inspiration that you can totally pair Chelsea boots with a pantsuit!
10. Dress up with Vitello Khaki Low Chelsea Boots
Image: Pinterest
As a truly versatile shoe, Chelsea boots look great with basically every outfit, from jeans to skirts and dresses. Try pairing your brown or black Chelsea boots with a midi dress, like the girl pictured below.
This look is perfect for any outing, get-together, lunch date, or even a more formal occasion. For a formal event, you can layer the look with an overcoat worn like a cape (without putting your arms through the sleeves).
You could also swap out the ribbed dress for a flowy midi dress for a more casual event.
Wrapping Up
Chelsea boots are such a versatile and stylish shoe to have in any wardrobe. I hope these tips and different style combinations gave you some inspiration to make the most of this classic shoe and create some looks that feel totally you.