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Thrifty Wife Happy Life

Helping women love what they wear on a budget

Trends to Try- Chelsea Boots

December 3, 2021 by Katie Haller

Outfit ideas with Chelsea boots
I’ve been on the hunt for a pair of Chelsea boots all fall.  This was a trend that I have been wanting to try, but I wasn’t sure if it was for me.  I feel like these chunky style boots can look a little too young and edgy for my style, but when I started to think about how practical they could be in the winter months I started to open up to them more and more.  At first, I started looking at combat boots.  I tried on a few pairs while I was out shopping and I just couldn’t get into them.  It was something about the laces that I didn’t like, so then I shifted my focus to the Chelsea boots.  I tried on a pair at every store I went to, but I just couldn’t find the right pair.  Then finally I found a cute affordable pair of Chelsea boots (HERE) at Kohl’s. (Boots run big.  I went down a half size.)  They were under $40 and had everything I was looking for in a winter boot.

 
*This post contains affiliate links.

What is a Chelsea boot?

Don’t feel bad if you don’t know what Chelsea boots are because I needed to do a google search on them too!  A Chelsea boot is a pair of ankle boots that are close-fitting with an elastic side panel.  I actually have a pair of black Chelsea boots that I bought last year, but those ones have a pointed toe and they seem a little dressier than the rounded toe.

Where to wear Chelsea boots?

What I really liked about these boots was that I could see myself wearing them a lot.  They are extremely practical for someone like me who lives in a cold climate.  They are cute and stylish, yet they will also keep my feet dry in the snow and slush.  These boots are practical enough to wear while errand running to Target, but they can also be dressed up for a date night.  Having a pair of cute boots like this keeps me feeling stylish through the cold winter months.

How to style Chelsea boots?

I am still trying to figure out how to style my Chelsea boots.  Like I just said, they are very versatile and can be styled in so many different ways, but you really just need to feel it out with your wardrobe.  For me, I feel like they go great with faux leather leggings.  You can also wear them with jeans.  I prefer skinny jeans with a cropped-leg with these boots.  If the jeans aren’t cropped I will roll the jeans the same way I would roll them when I wear my other ankle booties. I also love how they look in a skirt or dress.  Tights are great to wear with them, but they also work with a bare leg as well.  Here are a few looks that I came up with for now.

Look 1: Midi skirt + Moto jacket

I love how these boots look with a midi skirt.  It’s the perfect way to winterize a skirt.  I also love how this outfit is dressy, but the boots give it a casual feel.
Chelsea boots with leopard pleated skirt and moto jacket
Top || Skirt || Jacket (similar) || Boots

Look 2: Jeans + Sweater + Scarf

I think any jean that is a little cropped look best with these boots, but you can always try rolling your jeans as well.  This pair (HERE) from Abercrombie has a raw hemline which I think goes really well with the style of the boots.  Adding a cozy sweater and a pop of pattern with my scarf completes the look.
Chelsea boots with a black sweater and jeans
Sweater || Jeans || Scarf (similar) || Boots

Look 3: Plaid shirt + Faux leather leggings + Cardigan

I love the buffalo red plaid, but this shirt can easily give off a lumberjack vibe, especially with the boots.  That’s why I decided to layer it with a black cardigan to break down the pattern and add a feminine vibe.
Chelsea boots with red plaid skirt and Spanx faux leather leggings
Shirt || Cardigan (similar) || Leggings || Boots

Look 4: Tunic + Faux leather leggings + Vest

I’ve been wearing this exact look with my slip-on tennis shoes, but adding the boots is a great way to stay warm and keep my feet dry in the yucky winter weather.
Chelsea boots with an athleisure look
Tunic || Vest || Leggings || Hat || Boots

Look 5: Mini Skirt + Cardigan + Tights

These boots look great with a skirt, but if it’s a shorter skirt I like to add some tights to the outfit.  If I wear a shorter skirt in the winter, I almost always wear tights with it.  I am way too lazy to keep up on self-tanning my legs in the winter. I’ve worn this look with my pointed-toe Chelsea boots, but I like how this pair is a little more casual.
Chelsea boots with a skirt and tights
Top || Cardigan || Skirt (similar) || Tights (similar) || Boots

Look 6: Sweater + Leggings + Long coat

This is my go-to style in the wintertime.  A cozy sweater, leggings, and a long wool coat to stay warm.  I love the upgrade a cute pair of boots can do for an outfit like this.
Chelsea boots with a long wool coat and leggings
Sweater || Leggings || Coat (similar) || Hat || Boots

Don’t forget to pin the post!

Chelsea boot outfit ideas

Related posts:

Default ThumbnailHow to Style Tights For Winter Default ThumbnailWhat Shoes to Wear in The Winter Default ThumbnailHow to Wear Faux Leather Leggings

Filed in: Affordable Fashion, Style Tips, trends to try • by Katie Haller • 1 Comment

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  1. How to Wear Chelsea Boots - Thrifty Wife Happy Life says:
    January 11, 2023 at 8:33 am

    […] 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 […]

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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
These black Converse Chucks are my first thrifted These black Converse Chucks are my first thrifted purchase of 2023 for $7.99! I found them at @goodwillmidmich! Here's a casual way to wear them with joggers! 

#thriftythursday #thriftfinds #goodwillfinds #converse #thriftedfashion #thriftstorefinds #thriftedfashion #winteroutfitideas #casualstyle #momstyle #momootd #momstyle #outfitinspiration #michiganblogger #joggerstyle
I've been in a winter outfit rut for the last mont I've been in a winter outfit rut for the last month. All I want to do is throw on a big cozy sweater with some leggings and call it a day. That’s why today, to help myself get out of my winter outfit funk, I wanted to switch it up a little bit and put together a workwear winter capsule wardrobe post.

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
My husband and I have plans to have a night away f My husband and I have plans to have a night away from the kids this weekend. I've been brainstorming some outfit ideas for our date night. Which top do you like best with these jeans? 

🛍How to shop my outfits🛍
✨Download the free @shop.ltk app and follow @thriftywifehappylife for all my outfit details! 
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Do you have a short cardigan in your wardrobe? Her Do you have a short cardigan in your wardrobe? Here are some ways you can style them for winter! 

This sweater is out of stock but I linked some of my favorite short cardigans on the @shop.ltk app! Follow @thriftywifehappylife or go to the link in my bio! 

#cardigans #howtowearit #outfitideas4you #winteroutfits #sweaterweather #whattowear #midweststyle #michiganblogger #momstyle #momoutfits #styletips #styleinspo #styleblogger #momstyleblogger
🖤 What I wore this week as a SAHM! 🖤 I have 🖤 What I wore this week as a SAHM! 🖤

I have another round up of cozy outfits! I have to admit that I have been in a bit of a style rut! The lack of sunshine has made it really hard for me to feel motivated to get creative with my outfits and I've been finding myself repeating the same clothes over and over again. 

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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Get ready with me on a gloomy winter day! Even whe Get ready with me on a gloomy winter day! Even when I have no plans of leaving the house, I still want to wear an outfit that makes me feel good! Cozy sweatshirts, leggings and socks have been helping me get through these dark winter days. 

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
More pictures is a request I have gotten from a lo More pictures is a request I have gotten from a lot of people in the last year, so I'm going to do my best this year to  incorporate more picture posts! I miss them too! 

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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