How to Wear Chelsea Boots and Jeans
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Looking for some tips on how to wear Chelsea boots? This post is full of information on how to style this popular boot different ways, including how to wear Chelsea boots and jeans. From casual to dressy, this versatile and comfortable boot is one you can incorporate into several different outfits. I’ll show you how!
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Living in the Midwest, I wear Chelsea boots a lot! For me, they are a three-season shoe. The material and sole make them perfect for rainy Spring, Crisp fall, and cold (sometimes slick) Winter. I have had this pair for nearly 10 years and reach for them all the time. They are affordable and have held up really well. My favorite feature is that they slip on and off easily.
Let’s take a look at some Chelsea boots outfit ideas. To shop my outfits, click “outfit details” below the image.
How to Wear Chelsea Boots and Jeans
1. Wide Leg Jeans
Chelsea boots are great to wear with wide leg jeans because of the slim shaft. The boot sits nicely under the pant leg without getting bunched. Baggy fit jeans are trending, therefore you can easily achieve a fashion forward look by wearing Chelsea boots with a wide leg fit.
Outfit Details
2. Flare Jeans
Flare jeans are back and they look so good with Chelsea boots! I love this combination because flares cover the boot shaft completely and make the outfit appear less casual. With this vibe, you can wear a top that is more dressy. This is my go-to Chelsea boots and jeans outfit when I want to feel more polished yet comfortable.
3. Chelsea Boots and Black Flare Denim
4. Ankle jeans
They key to wearing Chelsea boots and ankle jeans is to keep a slight gap between the boot and jean. For me, personally, this is about 1-1.5″. Most ankle jeans are longs and hit slightly below the top of the boot, which is also flattering.
5. Skinny Jeans
Skinny jeans and Chelsea boots is a versatile look. They can be rolled up for warmer temps, with a small gap of skin showing between the jeans and boots. Another way to wear skinnies to to tuck them into tall socks. This is my favorite combination for cold days.
Outfit Details
How to Dress Up Chelsea boots
In addition to casual jeans outfits, there are several ways to elevate outfits with Chelsea boots. Here are 4 of my favorite ways to dress up Chelsea boots.
1. Black Dress and Blazer
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2. Black jeans and white button down
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3. Slip Skirt and cashmere sweater
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4. Leopard Skirt and sweater
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How to Dress Down Chelsea Boots
Now let’s get to the goods. A vast majority of the time that I wear Chelsea boots, it is a super casual outfit i threw on while running out the door. Here are a few of my go-to casual Chelsea boots outfits.
1. Flare Leggings
Outfit Details
2. Joggers
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3. A Puffer vest
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4. Faux Leather Leggings
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What are Chelsea boots?
Chelsea boots are ankle boots with an elastic side panel and round toe. They typically have flat or lug type sole. Common materials include leather, rubber, and suede.
My go-to pair of Chelsea boots
I won’t withhold information on these Chelsea boots because they are too good not too share! Being one of the first ever pairs of shoes I purchased online, I didn’t think they would last, but they have! These Chelsea boots are my ride or die and seem to get better with age.
I’m all about investment pieces for the wardrobe, especially if those pieces will withstand the test of time. But these are actually budget friendly and durable! Definitely something you can wear over and over again. I did my true size.
What socks should I wear with Chelsea boots?
Depending on the pants you wear, there are several sock options to choose from. Here are some of my most worn socks with Chelsea boots:
Are Chelsea boots and jeans still in style?
Yes! Chelsea boots are timeless and versatile. They can be worn with various jean fits (skinny, straight, wide, etc.) and washes. I’ve had my Chelsea boots for nearly 10 years, which speaks to the timeless quality of this boot style!
Where to wear Chelsea boots and jeans
Chelsea boots can be worn nearly anywhere. With casual wear trending in today’s culture, Chelsea boots can be incorporated into several outfit styles. Here are a few common places I wear my Chelsea boots:
- School drop off
- Shopping
- Running errands
- Date night
- The movies
- Church
- Holiday events
- Zoo trips
- Museums
- Fall activities
- Playground (perfect with young kids)
SHOP MORE CHELSEA BOOTS
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