Ask Allie: How to Style Chelsea Boots

Fashion Advice How to Wear Fashion Trends

I saw your post about Chelsea boots just at the time I was looking for a shoe that could be worn in the winter that doesn’t have much of a heel and that wasn’t a tall boot (sometimes I just need a break!). I’m still looking for the right pair for me, hoping to go with a fairly traditional style, but could really use some outfit inspiration. I would typically wear them with pants and outside of work, running errands, going out with friends, etc. Any chance you’re working on a post that showcases outfit ideas for Chelsea boots?

A Chelsea boot is a great addition to a wardrobe for its versatility and amazing combination of trendiness yet classic style. They look modern, but will still be wearable for years to come. If you purchase quality and take good care of them (take them to the cobbler to be reheeled and resoled as necessary, have a day between wearings so they don’t get stretched out or stinky, polish and protect the leather), this is the kind of shoe you can have in your wardrobe for over a decade. A few ideas on how to wear them outside of the workplace.

how to wear chelsea boots dress


Chelsea boots are low and roomy, making them perfect shoes for days when you’ll be on your feet. I created this look for the sight-seer, spending the day at museums and historic homes. A shift dress is comfortable but looks nice if you enter an historic place of worship or decide to dine somewhere nicer. Fleece tights and a pashmina or scarf will keep you warm while maintaining style. The Chelsea boots give a modern downtown feel to the look, continue it with an on-trend crossbody bag.

weekend style leggings chelsea boots


Chelsea boots are the type of shoe you can easily slip on when dashing out the door. This is a very typical weekend look for me – heavyweight leggings or jeggings, a flannel or denim shirt, and a puffer vest. Chelsea boots work great with this look, just slip the leggings under the boots and head out. A bit of gold in accessories keeps you from looking like a lumberjack.

how to style chelsea boots night out


Chelsea boots can go glam for a night out on the town. Pair with a little skirt or leather shorts and black tights for a hip base to show off a fun top. For this look I kept it simple with a white silk shirt and oversized gold hoops. Add some kohl liner and a perfectly messy ‘do and you’re ready for Saturday night.

what pants with chelsea boots


Chelsea boots don’t have to be paired with leggings or tights; roll up some jeans to go above the top of the boot for a different look and let a bit of socks peek out. A Breton tee is a weekend staple; a swipe of bold red lipstick and a bright bag complete the look.

chelsea boots skinny jeans style


This is the classic look for Chelsea boots this winter. Tuck skinny jeans into the boots and top with a slouchy or oversized sweater for weekend cool comfort. Chelsea boots can be a bit chunky, balance their weight with a larger bag and bold accessories. A bit of nude gloss on the lips is the perfect way to add a bit of polish to a busy weekend.