How To Style Chelsea Boots 4 Casual Ways

In today’s article and video, I want to show you 4 different ways that I like to style Chelsea boots for more casual situations. Alright, I have to admit, not very long ago, I wasn’t a Chelsea boot guy. I just wasn’t a fan of how plain they looked, and I couldn’t understand why everyone seemed so crazy about them. Well, fast forward to now and I currently have one pair of these dark brown Chelsea’s and I have to say, I really like wearing them. In fact, I’ve only had this pair for a few months, and there’s a good amount of wear on them because I wear them a lot.

Chelsea boots date back to the mid-1800’s when Queen Victoria wanted a boot made without laces to make riding horses easier. They became popular in mainly equestrian circles and they were worn by both men and women. It wasn’t until about the 1950’s and 60’s when they picked up popularity in the UK because they were seen being worn by The Beatles and The Rolling Stones. They’ve remained mostly unchanged in design with the tell-tail characteristics of having elastic side panels and a pull tab at the back.

In my opinion, they go with just about everything and look amazing with just about everything. So today I want to show you 4 different ways that I personally like to style these particular Chelsea boots. Feel free to modify or swap colors with any of these pieces to suit your general aesthetic. The purpose for this video is to serve as just a general idea guide or outfit inspiration that you can use when putting your own looks together. Also, this can not only help with Chelsea boot styling, but really, just about any dark brown boot or shoe. Please take a look at the video I posted above to see all of the looks I put together.