Chelsea boots

I continue to work my way through my 10-sample set. Should have something to say about these fragrances soon.

In the meantime, we’re up to London this week for a flying one-day visit and surely I’ll have to write about that…

Today, however, it’s Chelsea boots because on and off I think about them. I would say they are my favourite style of boot. I have really good knee-highs (one flat, one heeled) and low lace-ups. But, I haven’t been able to find Chelseas I love in the right size for years. I wore the last pair, from Clarks, to bits. They were fine but not perfect (gusset wasn’t tight enough, went too high on my ankle).

Thing about Chelseas is they can be dressed up or down; well-designed ones can work with a dress (and I don’t mean a tunic). The best ones manage to look both rugged and refined.

I’ve looked at Marks & Spencer, John Lewis, White Stuff, Joules and others but nothing has been exactly what I want.

I have issues. My feet are small (UK 3, US 5). The best fitting shoes I’ve ever found were from French brands (ie, Freelance) or made in Italy. An aside: Years ago, we (my father, son and I) visited Florence together. On one of the last days, we took a long walk in the Boboli Gardens, exiting on to a street full of shoe shops. As my son was of an age when he was strapped into the buggy and usually slept when in it (particularly after running around in a big park) we stopped in a shop that had a great window display. My father left with a pair of shoes (I think only one, but I may be wrong); I left with two pairs and a pair of brown suede boots that I wore until they had holes in the soles (the shoes included a pair of loafers which have disappeared and a pair of ballet pumps which I still have and are still fine — we’re talking over 15 years ago).

I used to buy a lot of shoes from Zappos when we visited the US. We haven’t done that in years (ie, visit the States) so that’s not on the cards. I love the brand Canadienne (have another pair of great knee-high boots from them) but it’s not really available here.

Blundstone, an Australian brand, makes nice Chelseas, but their sizing doesn’t work for me (not small enough; pic from their website).

The brand that has – as far as I can see now – the Chelsea boots closest to my desired design are offered by Dr Martens. Not the ones with the classic DM tread sole but those that with the thinner, more refined sole, the Flora (the Graeme in men’s, I think – if I had larger feet I’d wear men’s Chelseas as there are more available that are close to my desired style; again, pic from their site).

However, whereas DMs used to be reasonably priced and almost everyone I knew no matter how little they earned wore them that’s not the case anymore.

Now, DMs are beyond trendy and cost not the earth but way more than I think they should.

Even after trawling through the 1,200 pairs of Chelseas on the Zappos site I still found that this type of DM is as close to what I want as possible. I guess that’s saying something.  There was a pair of Sebagos that were close but they strangely lacked pizzaz – you know, when an inanimate object gets close to ‘right’ but still lacks that ineffable oomph. The Floras have that pizzaz.

Another aside: I don’t like zippers on my ankle boots unless they were meant to have zippers (ie, not on Chelseas, not on low lace ups – I have a pair of fur-lined Skechers for our ‘winter’ with non-slip soles and they have zips and that’s ok).

I did a big cull of shoes over the past few years. I now have an upstairs closet with less than a dozen pairs of shoes that are beloved but don’t get worn much (heeled stuff, summer stuff). Downstairs, the boots live in the closet under the stairs (knee highs and lace ups). The walking shoes with Vibram soles live near the door. The ‘winter’ boots and the Chuck Taylors (what I mostly live in during spring and summer) are tucked under the cabinet in the kitchen – for some reason.

My yearning to buy a pair of Chelseas waxes and wanes. Right now, it’s waxing. I find that I look seriously at the DMs around every six months. So, I guess it’s that time again. We’ll see where this goes.

What about you? Is there an item of clothing you’ve been hankering after but haven’t found that perfect specimen?

  • SpringPansy says:

    I LOVE chelsea boots. Shoes almost always feel like a unicorn hunt for me — so hard to find fit, comfort, color, style, etc all in one. I love my Blundstones with jeans – my feet are wider than a B width so maybe that’s why they fit me well, but they are a bit clunky for dressing up. Still searching for the elusive dress up pair.

    • cinnamon says:

      Yes, even if I could fit into the Bludstones they are a bit less sleek than I want. Though I do love the multi-coloured gusset.

  • Dina C. says:

    This fall I ordered and returned four different pair of kitten heel pumps before landing on pair number five: black kitten heel sock booties. They were much more comfortable and still looked dressy with tights. I found a pair of grey suede lace-up (and zippered) combat boots by Sofft that I love. That was a long search since grey suede is an oddball search. Next unicorn hunt: a grey suede handbag that’s just the right size and shape. Good luck finding your Chelsea boots, Cinnamon. I understand how it has to tick all the boxes or it just doesn’t give delight.

    • cinnamon says:

      So frustrating that the perfect whatever we want doesn’t pop up on first search. There’s a shoe company here called Mod Shoes which offers things that would have felt at home in the 1960s. Alas, so far I’ve decided I don’t ‘need’ anything I’ve seen. As to bags, I’ve ended up buying from a company here called Matt Fothergill. They make the bags themselves and you can choose colour and colour of interior — and on the two I now own I was able to get them to change the length of the handles. Not cheap but worth it as I got exactly what I wanted and they’ll last forever.

  • Musette says:

    Clothing-wise, I lust after a wasp-waisted Winter parka (sans hood) that flares into a bit of a peplum. In black and in a deeep blue (to bring out my eyes! LOL!). I wear a lot of leggings and boots this time of year, so it would be a great fashion look. But WINTER. Nothing cute and thin. It’s 7F out there right now…


  • Musette says:

    I used to love, wear and own SO many stiletto pumps. Omg. Then… the sacrum-cracking injury coupled with Where I Live and What I Now Do (no steel-toe stilettoes allowed in the petrochemical plant, thankyouverymuch ;-)… well…

    I now live in dressage boots (as well as gripper ice boots) for Winter (one fall was bad enough – two was just stupid). Summer I wear cute tie shoes – that injury has limited my balance, even with daily yoga, so I have to make sure my feet are firmly ensconced. Neuropathy (also from the injury) doesn’t help.

    sigh. I miss those Stiletto Days…


    • cinnamon says:

      I love stilettos but there’s no way I could wear them. Just don’t work with my feet (so small I teeter). I discovered the ‘doesn’t work’ after buying a pair of Louboutins on a Paris trip (lord, they were beautiful — and I think they were on sale) which I subsequently sold on eBay (that covered Xmas gift costs one year).

  • Portia says:

    One day you need to go to Asia shopping for your shoes Cinnamon. Your shoe size is much more normal there and the choice is humbling.
    My favourite ever pair of shoes came from a small Chinese brand called Fato, it was like slipping my foot into a dream and they were so comfortable. I wore them till they fell apart on my foot,. about 5 or 6 years. Nothing that soft and luxurious was ever going to last.
    I also have a bashed up 25 year old pair of Gucci loafers that are still a delight to wear.
    Portia xx

    • cinnamon says:

      I had a pair of red lace-up Freelance flats (French) which were so perfect and lasted years. But, when they were destroyed Freelance no longer made that model. One of those times I wish I had bought backups. It’s like perfume…

  • Tara C says:

    I love my Blundstones, but they are big and I have to wear thick socks. Do let us know if you find something fabulous as I love that style too.

  • March says:

    Sooooo…. I own a lot of boots, my preferred footwear. And I think I have … at least five pairs of Chelsea boots if we’re talking about “short flat leather boots that aren’t slouch boots,” with one pair having a strap around the ankle, it’s those Docs you pictured, with a strap rather than elastic gussets. The problem is Docs take forever not to be too stiff, so. Blunnies are too big, I gave them to a kid. The perfect Chelsea boots should slip on (no zip) and I have a couple pairs with a hard leather sole, but I mostly go for Vibram as they’re so much more comfortable. In my defense, I walk a lot — probably a lot more than most people — in non-rural environs, on paved surfaces. They work with pants, with skirts … I love them, clearly.

    My lusted-for item that I think I’m going to have to have tailor-made is a high-waisted, very long gored wool skirt, preferably in some fabulous tweed. I can find some elements but not all in the same skirt. Unsurprisingly, UK eBay has much better long wool skirts and vests/weskits than we do.

    • Crikey says:

      May I recommend Totty Rocks in Edinburgh for a skirt like that? She’s not cheap, but her stuff is wonderful, and all made to order/measure and she’ll customise as needed (e.g. lengths, fabrics.)

      • March says:

        omgggggggggg I want alllllll the tailored things, and that high-waisted waterfall skirt is exactly the shape. Thanks. Her prices aren’t cheap, but they’re certainly fair!

        • cinnamon says:

          If you decide to do it and need help facilitating (ie, have sent here and then onward if turns out to be cheaper) just shout.

          • March says:

            Thank you! Thus far I’ve held off because the waist is so precisely fitted, I keep pondering whether I should try to buy the fabric myself and find a local tailor. But going with a shop that already knows how to do that shape has its advantages (e.g., I think the waists may be lightly boned, just to keep them upright and flat.)

    • cinnamon says:

      What do you wear in warmer weather? Strangely, it used to be a lot easier to find boots I liked. I don’t know what’s happened in the past five or so years. Plus, I have skinny ankles so some Chelseas just gap too much. I have a feeling I’ll end up with the DMs at some point but I’m not there yet. Or, maybe I’ll make it back to Italy and I’ll find the perfect pair …

      • March says:

        I feel like chelseas cycle in and out of fashion and sometimes they’re everywhere … but I get most of mine secondhand (eBay, Etsy, thrifting). Easy for me, I’m a US size 7, but for you much harder. In my “before” life in D.C. I wore flats for work, but here it’s boots (and sandals) in summer. I have foot issues and need a structured footbed/support, boots are generally much easier for me to walk in than flats, which tend to be … flat and not supportive, even fairly nice ones, although there are exceptions. I used to commute (subway) in trainers but that’s the only time I wear them.

      • Crikey says:

        Have you tried the children’s sizes in DMs? I’m a small uk3, and often find they fit me better (and are masses cheaper). Though most of the boots have side zips for little fingers which probably rules them out for you

  • Teresa says:

    What about Blundstone? Saw
    Some nice ones with elastic gores on both inside and outside of ankle.

    • cinnamon says:

      Afraid not. Even the smallest women’s size is too big for me and the children’s boots look sort of weird.

  • Teresa says:

    My problem is opposite yours…I wear an 11wide because of a very high arch and instep…I subscribe the the adage ‘If the shoe fits….it’s ugly’ LOL and it usually is. The brand that fits me well is Birkenstock whose footbed and shoe print I refer to as ‘caveman shoes’….oh, well….

  • alityke says:

    Hi Cinnamon, have you tried checking out saddlers or country clothing outlets? Sounds strange but my best ever Chelsea boots have been jodhpur boots. The last pair came with zipped & buckled over boot that made them into a flat knee high riding boots. They weren’t cheap but bring another small footed female they were counted as a children’s boot & we’re VAT free. Mine were a rich tan shade but they also had black.
    The height, ankle fit & styling were perfectly classic.
    I had them & wore them for about 20 years though we do have a proper cobbler who hand sews & rebuilds leather soles

    • March says:

      So true — my all-time favorite boots were wine-colored jodhpur boots, over the ankle with the strap. I wore them for more than a decade, until the strap broke, and I stupidly got rid of them (because it didn’t occur to me that the strap could be mended!) I got them at a thrift store as a broke college student, and they were clearly expensive boots, beautifully made.

    • cinnamon says:

      I had looked at riding sites a few years ago. Will have another go.

      • Alityke says:

        Check out if there is Sporting goods or Saddlery in your area too. Many stock suppliers & items that aren’t available online.
        Remember to check if nearby towns & villages have an any independent shoe shops too.
        Enjoy your search & good luck on finding just what you want