How to Style Chelsea Boots

Fashion Details:

The most popular boot this fall and winter is the Chelsea Boot.  The Chelsea boot is named after the popularity in the affluent and trendy neighborhood in London during the height of the mod scene in the 50’s and 60’s.  And the funny thing about style is that some things never go out of style, like the Chelsea Boot.  So here we are today in 2021 and I’m sharing how to style Chelsea Boots.

Chelsea Boots 

First you have to find the perfect Chelsea Boot.  While the overall style of most of them are exactly the same the color, shaft height and comfort does vary slightly.  I personally own the Miller Water Resistance Chelsea Boot by Caslon.  I picked them up on super sale, but they are normally $99, which is a steal.  The main reason I bought them was because they are water resistant.  While they took a couple wears to break in, I’ve been really happy with them. I went with my normal size, but cannot get a thick sock on with them.  So if you plan on wearing a thick sock I would size up.  Here are a few other styles of Chelsea Boots I’m loving.

How to Style Chelsea Boots

There are two defining features of the Chelsea Boot; the lug sole and the elastic shaft.  This is what makes them so easy to get on and off as well as so stylish.  When styling them you want to play off these features and let them shine.  I think it will be a cold Chicago winter so I focused on styling them for colder days, even snowy days.  I simply pair a print sock with my skinny jeans and cuffed the bottom hem up.  Having more sock showing is what really makes this look.  Plus having exposed skin in the winter isn’t fun at all.  And there you have it! My simple formula for how to style Chelsea Boots.

Don’t forget how to tie a scarf to keep you extra warm while wearing your Chelsea Boots!