59 Comments

They NEVER go out of style! I've had the same ones for more years than I care to cop to. 😁 Love these posts because no matter what "hard stuff" I'm doing in a day, they represent a very welcome relief...nothing like a bit of "pretty" to lift a "Girl of a Certain Age's" spirits. 💜

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Sep 17Liked by Kim France

Could we possibly get the fashion tips and rules around how to style Chelsea boots? What kind of pants look best/worst? Are we doing these with cropped pants only? Are leggings acceptable these days? I looove these boots but I'm always worried about which pants I am supposed to wear with them. Thank you!

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I was just thinking the same thing! I feel like they only look good with skinny jeans, or croppy straight jeans, but not wider/baggier pants (which I find don't look great with ANY boot which is why I don't understand how to wear all these trendy pants in the winter!).

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And SAME

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Sep 17Liked by Kim France

Same!!!

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Sep 18Liked by Kim France

Maybe I'm doing it wrong, but I wear mine with trouser jeans and full-length pants. And with tights and skirts/leggings and tunics.

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I have a hard time styling lug sole Chelsea boots, too. After trying many combinations the best I came up with is a straight, demi boot cut, or slim leg jean, slightly cropped. At least that’s what worked for me. In general I’m not a fan of lug sole boots-except I do like the Blundstone boot. The ones I have are waterproof which is the only reason I wear them. I bought a pair of ankle boots from Flattered last year and they are much easier to style. Plus I got them half off.

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Otto Tootsi Plohound! Oh the memories. Somewhere in the back of my closet there’s still a pair of their clunky loafers that I couldn’t part with.

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I still have some shoes & boots from Otto Tootsi Plohound! I was so obsessed with that store (I am referring to the original one on West Broadway though) that I became friends with the manager. When my husband pried me out of NY so he could do his transplant fellowship at Wash U in St Louis, the manager sent me Polaroids of all the new styles each season so I could buy them by phone. This was 1988, 1989, 1990. There was no internet, no catalog then. I still have some of those Freelance Chelsea boots & also sandals. It was the best shoe store & I still miss it now that I am back in NY for the last 20 years. As for the store on Amsterdam, was it Na Na?

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author

It *was* Na Na.

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Sep 18Liked by Kim France

Oh wow, Na Na! I still have a pair of Docs I bought there in the 90s.

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I love this style of boot but even with elastic I have trouble getting them on because of my stupid high instep which makes any boot without a zipper impossible to get on.

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Sep 17Liked by Kim France

Me too! Very high instep so can’t pull on any boot. Can anyone recommend a stylish boot with a side zipper?

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This one. Available in black and brown.

https://www.eileenfisher.com/coin-leather-bootie/EF49381.html

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Was the store on Amsterdam Na Na?

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author

YES!! That was it!

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Omg we had Na Na in LA too

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I think they originated in LA.

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Sep 17Liked by Kim France

Blundstone just dropped sued Chelsea boots:

https://www.blundstone.com/black-premium-suede-leather-chelsea-boots-womens-style-2405

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Sep 17·edited Sep 17Liked by Kim France

Do any of these (or other similar) have a super supportive insole? Think Birks level support. I can't wear anything without that level of support for more than an hour these days and walking on cold hard ground would cut that time in half. Truth be told I'm in Birks or tennies all day everyday but I would love to mix it up.

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author

Never underestimate the power of a good insole.

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Sep 17Liked by Kim France

Birks makes a Chelsea boot! Actually they make a few. The Prescott is a good one.

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Sep 17Liked by Kim France

I remember the store on the UWS that you're talking about, and I can clearly picture the facade, but I'm blanking on the name. I think it's lost in the mists of time.

I adore Chelsea boots, and that first pair is really calling my name. The pointy-toed ones are tempting too. My go-to pair are these no-name-ish ones: https://a.co/d/2BDSNIB, which are improbably comfortable even for long walks and have been with me for three or four years now. I'm planning to buy them in brown too.

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Sep 17Liked by Kim France

I love these, especially the ones with brogue-ish details. I’m a purist and usually avoid lace up ankle boots with zippers on the side, but I might have to make an exception for these. Thanks!

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Sep 18Liked by Kim France

I remain committed to Camper as a source of comfortable Chelsea boots. Year in, year out, they offer a wide range of walkable styles at a very reasonable price. Wish they were still made in Europe and lasted as long as the Campers of old, but that seems like an unreasonable ask in today's world.

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Sep 18Liked by Kim France

I love them, but wish there was a comfortable vegan option.

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I love my Blunnies. I'm on my 4th (?) pair I think?? I wear them all year round in Chicago. May need to get the orange elastic ones now. Hmm. Quite the quandary!

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Dooo Eeeet!!!

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Sep 17Liked by Kim France

Love mine from Miz Mooz!

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Sep 17·edited Sep 17Liked by Kim France

I have some Miz Mooz ones too, from approximately 2015! Every winter I think I'll replace them but they somehow haven't yet fallen apart.

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Sep 17Liked by Kim France

I’m a huge fan of Penelope Chilvers for Chelsea boots. They have shearling-lined ones that are lovely. It can be a bit of a pain to order UK brands in the US but they make it pretty easy. They are also on the pricey side, but I’ve had two pairs for years and the quality is excellent.

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Sep 17Liked by Kim France

I have a pair of green suede Chelsea boots and they are very cool looking! Not the most practical for wet weather but so cute.

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Oh wow! Can’t believe my memory still works! Got my first pair of clumpy black oxfords there. Those were the days when sales help could for some reason afford to be snooty. After 9/11 it changed. Do you remember another shoe store that was in SoHo, Giraudon? They also had shoes like Tootsi Plohound.

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