How to Style Chelsea Boots: 5 Looks

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A member of the Wardrobe Oxygen community reached out asking for tips on how to style Chelsea boots. She wanted the style and convenience of this classic pull-on boots but wasn't exactly sure what to wear with them. Below I share some sample outfits to show ways to wear Chelsea boots in a stylish and practical manner.

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?

How to Style Chelsea Boots

Chelsea boots are a great addition to a wardrobe for their 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 Chelsea boots 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 style Chelsea boots outside of the workplace

Create a Continuous Line with Matching Tights

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.

Style with Leggings and a Tunic-Length Shirt

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.

Dress Up with Luxe Fabrics

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.

Pair with Rolled Jeans and Statement Socks

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.

Pair with Skinny Jeans and a Voluminous Sweater

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.

A woman with curly hair wearing a plaid blazer holds a green fur coat over her shoulder on a city street.

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  1. Thank you so much for giving me permission to wear Chelsea boots with leggings! Not sure why I needed it, but apparently I did. You’ve greatly expanded my choices when getting dressed in the morning as I can’t seem to stop wearing my burgundy Dr Martens this winter.

  2. I love all these looks! I’m definitely going to have to try them out – I own component pieces for most of these. 🙂 (but not leather shorts. Can’t do leather shorts. So far out of my comfort zone… Nope!)

    1- the grey sweater in the graph of the last look doesn’t look like the ones linked… Do you know where it’s from?
    2- you mention wearing thicker tights… What are search words to find thicker material that can be worn as pants? Ponte leggings? Any brands you’d recommend for quality/price? 🙂

    1. Unfortunately I made the collage knowing of a similar sweater for sale and with the after Christmas sales it was sold out and I had to find an alternative. That exact sweater is from New Look: as for thicker pants, I usually look for ponte (though there’s varying degrees of weight), scuba (not all is shiny), or a wool knit. My all time favorite ponte pants were from LOFT though they don’t have them any more. NYDJ’s ponte leggings and skinny pants are a nice weight though their basic pants are very lightweight. Lands’ End also has great ponte knit though the sizing and fit can be wonky on some.

      1. Thanks for the quick answer and the help! Thicker leggings (ones that don’t feel like tights…) are surpisingly difficult to find.

        1. FYI today I also saw some Smartwool leggings at Nordstrom, they’re online. I don’t know how thick they are but I bet they’re warm. I may order them, this winter is COOOLD! If I do I will be sure to review them here!

  3. Wow! What fun to scroll through my Facebook feed this morning to find you answering my question about styling Chelsea boots. Thanks for taking the time to do this! This helps a lot and I love the outfit suggestion with the leggings.

  4. Absolutely love! I’ve debated a pair like this in a black or a neutral (which might be better for my climate) but with my denim, feel like my shorter self looks stumpy when I have rolled denim on top of the boot. yay or nay? I’m just such a denim girl. Though you have provided a lot of inspiration. Love the first two looks.


    1. I find with my short curvy self I look best with a neutral bootie with some heel. I have a pair of beige suede ankle boots with a wood heel that I often wear with my boyfriend jeans. The black boots I have don’t give as good of a leg-lengthening look but that hasn’t stopped me. 🙂 I’ve been doing the sock to fill the space between jean and boot and that seems to help me look longer and not break the line as much.

      1. I am also short and curvy and wore my black chelsea boots with a pair of cropped jeans recently (more like boyfriend jeans… I don’t do “true” cropped anything) and was surprised how good I felt and how cute it looked! Such a fun shoe.
        By the way, Allie, can you tell me what kind or color of sock you use to fill the space? My sock didn’t really show between the jean and boot, but I would like to try that look.

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