Trends to Try- Chelsea Boots

in , , , by Katie Margaret, December 02, 2021
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. 

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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


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





Affordable Chelsea Boots




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Chelsea boot outfit ideas


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