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Thrifty Wife Happy Life

Helping women love what they wear on a budget

How to Wear Chelsea Boots

January 11, 2023 by Katie H.

6 winter outfits with chelsea boots

One popular question that I have gotten a lot in the last couple of months is how to wear Chelsea boots. I actually wrote a blog post on how to wear Chelsea boots a year ago, but I keep getting asked about them, so I figured that I would do an updated post this year with some new outfit ideas to wear with Chelsea boots.

*This post contains affiliate links.

I have had my Chelsea boots in my wardrobe for over a year now and wear them all the time. What I like most about this style of boot is that it’s cute and stylish, but also practical to wear in the winter months. A lot of shoes are just not suitable to wear in the winter weather. Although this pair of Chelsea boots aren’t considered waterproof, they still keep my feet nice and dry and I don’t worry about the material of these shoes getting routine. When they get dirty, I just take damp clothes and wipe them off.

Another thing I like about my chelsea boots is how easy they are to style. They can be worn with almost any style of pants or skirt. Here are some outfit ideas that you can try with your boots this winter.

*Sizing info- My typical shoe size is 7 1/2. I found that this pair of boots run big. I sized down to a 7.

How to wear Chelsea boots

1.) Leggings

Leggings are usually my go-to winter pant option for wearing my Chelsea boots. You can wear them on their own or add a cute boot sock to the look. I personally like to add boot socks when it’s cold outside to give my feet some extra warmth.

Leggings with chelsea boots and a turtleneck sweater
Leggings with socks and chelsea boots

Sweater || Leggings (similar)|| Boots || Socks

2.) Straight-leg jeans

When it comes to wearing straight-leg jeans with Chelsea boots I like to opt for a pair of straight-leg jeans that aren’t too wide. Something in between a skinny jean and a straight-leg jean is perfect. You also need a pant that isn’t going to hit your boot at the wrong spot causing it to bunch up. It takes some trial and error to figure out the right combination. You can read more about how to style straight-leg jeans in the winter HERE!

I also love to wear a pair of boot socks with my boots. It’s a great way to help keep your ankles warm when you are wearing cropped straight-leg jeans.

Straight-leg jeans with chelsea boots

Shirt || Jeans (similar) || Coat (similar) || Boots || Socks || Necklace

3.) A sweater dress with tights

I love the look of Chelsea boots with a dress and black tights. They give your dress a little more of a casual look. If you live somewhere cold, fleece-lined tights are a great option to wear with a dress and Chelsea boots.

Black sweater dress with fleece lined tights.

Dress (similar) || Tights || Boots || Necklace

4.) Black jeans

Black jeans are a great pant option with Chelsea boots. I always love an all-black base with a neutral layer over it. The black pants do a good job of helping my legs look longer with the flat round-toed boots. As I said before, you want to make sure that your pants and boots hit at the right spot so they don’t compete with one another and cause bunching. If you are struggling with the length, you can always roll your jeans or cut them for a better fit.

Black jeans with chelsea boots and a blazer.

Top || Jeans (similar, similar) || Blazer (similar, similar) || Boots || Necklace

5.) Skinny jeans

Pairing skinny jeans and Chelsea boots together can be the perfect way to update some of your skinny jean outfits. I like to roll my jean a little at the bottom so they hit just on top of the boot. It’s the same way that I style my skinny jeans with booties.

Skinny jeans with chelsea boots

Sweater || Jeans (similar, similar) || Boots || Necklace

6.) Midi Dress

Chelsea boots often go really well on their own with just a simple dress. They have a bit of an edgy style to them, so it’s always fun to explore that when putting together outfits. This simple winter dress is a great way to style these boots. I added the faux leather jacket to complete the look.

Midi dress with chelsea boots.

Dress || Jacket || Boots || Necklace

Make sure you are following me on Instagram for more style tips!

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6 ways to wear chelsea boots

Related posts:

Default ThumbnailHow to Style Tights For Winter Default ThumbnailHow to Style Straight-Leg Jeans in Winter Default ThumbnailTrends to Try- Chelsea Boots

Filed in: How to Wear it, Uncategorized • by Katie H. • Leave a Comment

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Hi I'm Katie! Welcome to my blog! I am on a mission to help women build a wardrobe that they love without spending a lot of money doing it. I believe that everyone has the right to feel good in their outfit, no matter what your budget is! I am excited to have you here!
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Katie || Affordable Fashion
I found some fun pieces on my latest @amazon order I found some fun pieces on my latest @amazon order! Here's how they look! 

T-shirt hoodie- $21.50- I love this top! It feels like a t-shirt so it's perfect for layering under jackets! 

Flare leggings $24.99- aka yoga pants. These pants take me back to the early 2000's. I am loving them! 

Tunic $24.98- Love this tunic! It's a great length. Perfect for layering under sweaters! 

Matte faux leather leggings- These are the best faux leather legging dupe for the Spanx I have found so far! 

Wide leg trousers- I have loved these pants on everyone else, but they weren't my favorites. I still felt that they are a great pair of trousers! 

Check out my stories for more details! Everything is linked on the @shop.ltk app and also in my Amazon Storefront. You can find both in the link in my bio!! 

#amazonhaul #amazoninfluencer #amazontryon #amazonfashion #amazonfinds #affordablefashion #amazonblogger #momstyle #everydaystyle #momootd #casualstyle #winterstyle #leggings #flareleggings #fauxleatherleggings
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Today on the blog I am sharing 15 neutral workwear pieces with 20 outfit ideas. Head over to the blog for all the outfit details! 

Blog- www.thriftywifehappylife.com (link in bio)

Capsule items are also linked on the @shop.ltk app! Follow @thriftywifehappylife for details or go to the link in my bio! 

#capsulewardrobe #winterwardrobe #winterworkwear #workwear #businesscasual #workingmom #workwearstyle #workwearwednesday #workstyle #whattowear #howtowearit #momstyle #affordablefashion #teacherstyle #shopyourcloset
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🛍How to shop my outfits🛍
✨Download the free @shop.ltk app and follow @thriftywifehappylife for all my outfit details! 
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That's why this week I built each outfit around one piece in my wardrobe that I haven't worn in a while. I have a lot of clothes and sometimes rediscovering pieces that I love help my outfits feel more fun and creative! 

🛍How to shop my outfits🛍
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Out for details 
Leggings- @amazon
Sweatshirt- @oldnavy 
Tunic- Old Navy
Necklace- @silverado_jewelry (code: KATIE10)
Socks- Amazon

Shopping details are linked on the @shop.ltk app! Download the free app and follow @thriftywifehappylife or go to the link in my bio! 

#ltkstyletip #ltkunder50 #sahmoutfit #outfitideas #outfitideas4you #grwm #momstyle #momootd #momiform #cozyoutfit #momlife #winteroutfitideas
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This leopard blouse is one of my favorite tops in my wardrobe! Which way is your favorite?

🛍How to shop my outfits🛍
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