Comfy and Chic Boots for Fall: The Chelsea Boot

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I can’t wear more than a 1” heel and need a new shoe for fall. I’m looking for something I can wear with pants and jeans to work and home.

I can’t keep up with trends, can you suggest a shoe for fall and winter that won’t be tacky next year? I don’t have to dress up much at work, I wear a lot of casual pants and sometimes leggings with tunics or dresses.

I have an answer for both of you – the Chelsea boot. A classic short boot that has been chic for years and likely will be for many to come, this boot is quite popular this fall making it easy to find in a variety of colors, styles, and pricepoints. Also known as jodhpur boots or Australian work boots, this style of boot has been around since the Victorian period, so you know it won’t go out of style any time soon.

Chelsea boots are made to be easy to slip on, with their signature elastic gussets on the side and a pull tab on the back. While such boots are obviously styled with trousers and jeans, current trends show Chelsea boots slipped over skinny jeans and leggings or styled with tights and skirts. It’s refreshing when current trends are classic AND comfortable! A few favorites I’ve found on the web:
comfortable stylish low heel shoe for fall winter
1. Trotters ‘Leah’ Chelsea boot is of supple leather with a rubber footbed, making it comfortable and flexible. Available in narrow, medium, and wide widths as well as two classic colors (black and cognac), this is a great choice for the fussy foot who wants chic style. $144.95

2. For you heel-aholics, there’s a Chelsea boot for you too! I’m drawn to the ‘Zane’ from Chinese Laundry with its stacked wood heel and scalloped shape at the elastic. Cognac would look great with distressed denim, and the black and wood combination would look fantastic in winter with a chunky turtleneck, a-line mini and thick tights. $119.95

3. For those who like to make a statement with their feet, the ‘Meow’ from Ganni Veronica is perfect for you! A tan and black leopard print on leather will complement much of your wardrobe and a wood heel keeps it fun and fashionable. $342.77

4. A Chelsea boot doesn’t have to be of glossy leather, and the ‘Aimee’ from Naughty Monkey shows that a slouchy suede Chelsea can be quite chic. Available in black, tan and taupe, this is a bootie that would look best with casual looks, be it boyfriend jeans or wool tights and a dress. $79.95

5. Want to take full advantage of the chunky soles and heels that are back on the scene this season? Then you may like the ‘Alter Ego’ Chelsea from ASOS. While the sole is trendy, the rest of the styling is classic, making it a good choice if you plan to incorporate the chunky shoe into your long-term personal style. $104.74

6. Why keep the Chelsea boot to classic footwear, when it’s such a wearable style? The Chelsea makes for a great pair of rain boots, as evidenced by the ‘Crain’ by Aldo. Available in black and brown rubber, it’s a smarter workweek choice than candy-colored knee-high wellies. $50.00

7. Cole Haan is my go-to for classic and elegant work shoes. Their ‘Draven’ Chelsea boot is no exception with a higher but still wearable heel and classic lines. While it’s available in basic black and brown for work or play, the Maple Sugar Suede would pair beautifully with a cream fisherman’s sweater and distressed skinny jeans. $298.00

8. The ‘Ava’ from Paul Green is one of my favorites because it has a fun spin on the classic Chelsea. With a medallion stamped toe box, the shoe stands out in a crowd but is still conservative enough for the workplace. Available in black, Cuoio (a light cognac), and Truffle (a taupe that would look great with brown, black, or gray). $365.00

9. Can’t go wrong with a classic! The ‘90s are back, so no better time to get your Doc Martens fix with their ‘Flora’ Chelsea boot. A low heel and DM’s well-known quality, these are available in a polished black leather that will only get better with wear and time. $139.95

10. For those who desire little to no heel, the Brogued Chelsea Boot from Boden are a great choice. Available in black, Red (which looks more like Cordovan to me), or Navy, this boot would look great for the office but also adorable with skirts and dresses. $198.00

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. I got myself a pair of Chelsea boots off Amazon for rainy days walking to work and around town. They’re as comfy as all get-out. My only problem is that they’re so casual in style they don’t go with about half of my work trousers. I will have a go with skirts and tights when it gets a bit colder.

  2. Allie, I am fine with affiliate links, but making pictures require turning ad-blockers off is just one step too far. It makes your blog seem like you are only out for the add money. I hate to say it, but my opinion of you just dropped a notch.

    1. I didn’t know it did that, thanks so much for letting me know. I won’t be using images like this again. I switched affiliate programs and this one has a bunch of new tools I’m trying out. This is the first time I’ve used this one with the photo. I don’t want to make this site harder to use so I will not just stop using such a tool for images, later
      Today when I get the chance I will remove the current image and replace it with a traditional JPG. I don’t know usability issues until I hear from you folks, and

  3. I have a pair of Chelsea boots that I purchased about 10 years ago. They still fit, look great, and are still in style!!!

  4. Omg, one of my favourite styles forever. Classic “beatle boot” — you can sometimes find them in outrageous colors too. I had some in purple suede that I loved (& wore until they were destroyed).

  5. Marshalls has really Chelsea cute boots for low prices if you desire a lower price point. As a Marshalls junkie, I’m just throwing that out there. I love all the boots you showed us, Allie!

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