The problem with Chelseas: it's me!

So, yesterday I was at the Burlington Mall (a big mall with a poor-man's Nordstrom -- very small shoe dept). Anyway, I tried on a bunch of low black boots -- chelsea and chelsea-like. If you've seen a few of my recent posts, you know this search has caused me a lot of pain.

I realized a few things yesterday. First, the term "chelsea boot" has many interpretations. Second, the interpretation I have had in my head is really the one that is not going to work for me. I cannot believe it has taken this long for the penny to drop. What I love in theory is the flat pull-on short black boot with the roundish toe. But, I really do not love a round toe on a flat boot. (Anyone remember the Frye Philip shorties that I consigned for this very reason?) I nearly had a migraine by the time I realized this. (I felt quite a bit like Cinderella's step sister, trying to force myself into a style I am wholly unsuited for.)

I also realized that I do not want to spend more than $250 on booties, and less is better. I am hard on footwear, and I like to change things up every season or two. It does not make sense for me to spend extreme amounts on luxe footwear. (I did try on a pair of AGL "Cherry" booties that were amazing at $450, but really, the likelihood is way too high that I would be bored with them by February.) I'd much rather find the most comfortable mid-range footwear I can and wear it for a season or two, pass it on, and replace it. I'm not into longevity for my feet, and I actually have been quite happy with Zara and Topshop footwear, which lasts just about as long as my love for it does.

Ultimately, I brought home a pair of Madewell chelseas: the Joni bootie, very comfortable, slightly Western (and the ankle opening is not nearly as big as it looks in this picture). The Western styling gives me a little pause, but I really like how they look and feel on. Still, there are a couple from Zara I also have my eye on, so I am leaving the Jonis in the box until the others arrive.

I'll probably be looking for feedback once they are all here, but for now I wanted to share the learning. It's been a painful but productive journey.

Zara

Flat Leather Ankle Boots

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Zara

Block Heel Leather Ankle Boots With Stretch Detail

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Madewell

The Joni Boot in Leather

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8 years ago

Joy

Veteran

Looking at the photos, I like the Joni best. They have a bit of a heel...more than the 1at and less than the 2nd..

cheryle (Dianthus)

(website)

I agree with Joy as long as they are not too baggy at the ankle. The heel is a comfortable height without being flat.

I am in the same boat with chelsea boots. I have purchased a few pairs including the Doc Faun this year and have finally accepted that this style does not work for me. They rub uncomfortably on the front of my shin. Pah.

CocoLion

It's good to understand your needs. I hear you on getting sick of styles quickly. I look forward to hearing how they work for you.

I think for me the realization has been the opposite. That I demand the highest quality footwear and feel it will be the centerpiece of my style. Whenever I trade down I have regrets, unless I am buying for a seldom worn category like pumps. Then I'm fine with a mid-range or lower end shoe as long as it's made out of leather.

Are you coming to Seattle?

viva

Oh Denise, sadly I am not coming to Seattle! It's turned out to be a really busy work month and my daughter, whom I was also hoping to visit in Portland, is out of town -- so for both reasons I am skipping this get together. Can't wait to see your pictures, though.

Bijou

It is so good that you realised your preferences before buying the wrong boot - I think I would have fallen into that trap! Thanks for sharing the learning journey, I find these posts very instructive. The Joni boot looks great, I hope you enjoy it very much.

catgirl

The Burlington Mall! I used to shop there. I totally see your issue and it's why I was struggling to find the right Chelsea boots for you. We need to design our own boots somehow.

Suz

Burlington Mall!! I have shopped there when Mr. Suz's mother was still alive.

I get what you are saying about the boots and this is why I love my Stuarts SO much. Maybe the Jonis are similar?

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If I could afford and justify these Aquatalias...

UmmLila (Lisa)

Love pointy toe boots. Can't justify another expensive pair this year,

Saks Fifth Avenue

Aquatalia Hedy Embossed Leather Ankle Boots

$550.00 $165.00

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Jaime

I prefer the look of the Jonis out of these three. The first Zara one looks good but the wood heel gives it a different vibe and the second is too high for me to put in the same category. Good luck!

Ariadne

I have two pairs from the GAP that are very similar to the Zara pair and I wear them all the time.

Elizabeth P

I've been trying to replace a pair like this for years... I keep missing slightly, and don't know why. Meanwhile the oldies just get beaten further and further into the ground. It's hard to find the perfect black boot! I do like the ones you've found. also really liking Suz's...

Colette

Thank you for your update. I mentioned before that I'm watching your boot search very closely because my search continues as well. You are so right about the different interpretations of Chelsea boots. I've ordered and tried on so many casual Chelsea style booties my head is spinning. I tried the SW Apogeelo and while I love them, they are a bit too dressy for what I need for day to day wear. If I worked in an office I would have kept them. And I decided that I would prefer to spend less, if I can. So, I've ordered another round and I'm hoping one of them work. I sure hope one of your picks works for you!

unfrumped

Very smart!
It took me a long time to realize I need mostly boot(ies) that are narrow enough at ankle for "sort of straight" pants to fall over, and/or I need a "slight bootcut" pants capsule specifically for pants to slide easily over ankle boots.
The boot look is very good for adding some "polish" to relatively conservative work pants, but the 2 need to work together.

Vicki

Viva, your thread was made for me and so timely, because I, too, have been struggling to define what a true Chelsea boot is and I realize they come in many variations and, as buyers, we have different preferences.

I prefer a low heel with a pointy toe similar the one UmmLila shows above.

The search continues and I'll be reading this thread for more discoveries. Thanks for talking about this.

fwiw I always thought the defining feature of Chelsea boots was the elastic gore at the side.

My husband is the world's biggest Chelsea boot fan. I can't even count how many pairs he's gone through in the last 25 years,

Vicki I bet you'd like the Acne Jensen or Marc Fisher Chelseas too.

Well, you may well be onto something Lisa. The Jonis, described as a Chelsea despite a bit of a western vibe, are slip on with the side goring. So there you have it. I now own Chelseas after all.

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