5 Ways To Wear Chelsea Boots | an indigo day

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Come fall, it’s all about the booties. Pair them with dresses, skirts, jeans and even your favorite leggings. But one of my favorite styles of booties is a Chelsea boot. I have several from waterproof ones, flat suede boots and my beloved heeled snakeskin Chelsea boots. A Chelsea boot is a distinct style and has a specific definition. I mean, you can just Google it, really! But I’ll do the hard work for you; a Chelsea boot is an elastic-sided, ankle-high bootie. Thanks, Google!

These types of boots can come in flat boots, high heeled boots and everything in between. And they come in all the colors and prints. From classic dark brown leather, to cognac suede, and even snakeskin, leopard and more. But it’s the elastic and ankle high shaft that makes it specifically a Chelsea boot. I have several pairs and you really can never go wrong with them. There’s so many ways to style them from business casual, to edgy looks out on the town, street style inspired and even just cozy casual outfits. Here’s a few ways to wear Chelsea boots.

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These are just a few of my favorite ways to wear Chelsea boots. From business casual outfits, to cocktails with friends, to just running errands. These looks are some of my closet tried and true favorites that I wear on repeat.

5 Ways To Wear Chelsea BootsPhotos by Hannah Lozano

Chelsea Boots With Dresses + Blazers

A blazer paired with suede Chelsea boots is a perfect edgy look. I just love a good long boyfriend blazer to complete an outfit. However, not only does this work nicely with a dress for those warmer fall days, but you can swap the dress for skinny jeans and a crew neck sweater for a streamlined look.

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5 Ways To Wear Chelsea Boots

Heeled Chelsea Boots With A Midi Dress

My snakeskin Chelsea boots are one of my most worn items in my closet. They go with all my favorite denim and sweaters since most of my closet is filled with earthy tones. But I do love it with a great dress like this midi sweater dress with a denim jacket. Another ideal transition outfit. But for colder days, add a pair of tights to stay warm!

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5 Ways To Wear Chelsea Boots

Black Chelsea Boots With Jeans

An easy everyday outfit that never fails me, is just jeans and booties. It’s a fall staple outfit for me. Add in any of your favorite fall tops from buffalo plaid tops, sweaters or even a nicer blouse. Top with a fall layer like a leather jacket or trench. It’s as easy as that! My tip is that whatever you can usually wear with your favorite sneakers, you can typically swap with a Chelsea boot.

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Dresses + Cardigans fashion

Chelsea Boots With Dresses + Cardigans

One of my favorite transition outfits from either summer to fall, or winter to spring, is a dress with a cardigan and a pair of Chelsea boots. It helps to bring those warm weather pieces from season to season effortlessly. This is a perfert smart casual look for a warm fall day.

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Faux Leather Leggings

Chelsea Boots With Faux Leather Leggings

Chelsea boots were meant to be worn with faux leather leggings if you ask me. I prefer either to see a sliver of skin with your jeans, or have a legging create a clean line through the bootie. Going all black is a great way to go. Leather jacket, faux leather leggings and black leather Chelsea boots is an easy and effortless outfit. Plus, it’s perfect for just about any occasion from grabbing lunch, to cocktails come fall and winter.


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