Help Needed Choosing Chelsea Boot

[TimothyF]

I found out Red Wing chelseas have a foam footbed, as opposed to thick leather insole, so figured I had to draw the line somewhere in terms of construction quality.

Right now what I'm wondering about the most is: What is the ideal Chelsea boot fit, and what does that feel like? And do you see the Chelsea elasticated boot as a walking shoe? Not talking about on your feet several hours, loafing about; but let's say at least 1 whole hour of brisk walking.

These are my fit experiences and challenges so far with a pair of Chelseas (which I thought felt pretty good on feet for 30+ minutes at the store). Thought I'd put them up here to see if they resonate or conflict with the community's experiences; in order of descending relevance

1. Heel slip

All the Chelseas I tried I can remember experiencing some-to-a-little heel slippage in store. I would assume to eliminate it completely my toes would get crushed by the far-too-small size. My thought was "If it slips just a little bit initially, then as the boot and sole break in slippage should be largely mitigated/eliminated". But preliminary experience makes me doubt this bit of received wisdom, as I had not taken into account the slow walking I did in store/at home, versus the fast walking outside that I subject the boots to.

Fast walking pushes hard on the front of the opening and instep areas; I think stretching out either the leather there, the elastic, or both. Such that heel slip is greater with fast walking than with a casual stroll. And I fear this stretch is permanent, which makes the heel slip bigger in the future. As I'm only in the beginning of my journey, please confirm or rebut my suspicions (in fact I'd love a well-argued rebuttal here!)

2. Pushing against the Accessory Navicular bone​

If you have no idea what the F&*% I'm talking about,
A) You are like me 2 days ago
B) You may or may not be part of the ~20% of the population that has the protruding bone on your foot

(I thought everyone had this, but now I know better)
I had a bad experience with an Edward Greens where the blucher facing on the inside seemed to "punch" that bone on my foot with every step I take. The (pricy) solution from a cobbler was to cut out that part of the inner facing, leaving a semi-circular wedge at the top of the shoe

Why I bring this up is wearing the Chelsea boot with some brisk walking brings back some of the pain I felt on those bones. Further data point is trying on RM Williams gardener in store, which also seems to aggravate that bone (even if in minuscule amounts due to the short duration).

Having not yet dug very deeply into the issue, I think the part digging into the bone could be the U-shaped seam between the leather and the elastic. The seam with tight stitching is likely the hardest part on a wholecut chelsea pattern. And my fear is that just about all Chelsea boots would place that U elastic in roughly the same spot relative to the foot's anatomy. So long-shot question, as this is admittedly an uncommon condition: Does my particular protruding bone doom me not to be able to wear this style of boot? (if you have this condition, and experience with Chelsea boots, I'd love to hear about it!)

3. Rubbing against little toe​

I think this issue is partly due to last shape; and partly due to the fact that the ankle is not 100% secure, and thus probably slides forward a bit with each stride. Obviously this is aggravated by fast walking. The last toe shape part I don't think is unique to Chelsea boots any ways, so there are probably a ton of toe rubbing Q&A all over the internet.

I ranked this issue last because
A) I think it is a more common issue, so likely to have some good consensus solutions
B) I believe over time the toe will push on the shoe leather enough to mitigate the discomfort, and if not a cobbler might be able to stretch it the rest of the way (but do tell me if this is wrong or dangerous to do!)


So yeah these are my musings as I'm working to break in my first pair of Chelseas, and contemplating whether the style is for me and whether I should try for pair #2 at some point. Hoping this is interesting, and provoking of some thought and discussion, which will help me learn more. Thanks!

 

[Blastwice]

Chelseas are like loafers and other laceless footwear: If you're buying RTW, it's best to try on in-store or alternatively know your exact size in a specific last/brand/makeup. If you want something that fits truly perfectly, you'd probably want to go with MTM for laceless footwear.

Wholecut patterns vs. non-wholecut will never make any practical difference from a quality/durability standpoint-- it's an asthetic choice, usually. The higher the price, generally the better leather. There are many good (more budget) leathers out there, but it takes a lot of experience to know which will look good over time and other qualities you might be looking for, so price can be a shortcut.

I agree w/ jack webb that Chukkas can be much easier to fit and a good alternative if you're having trouble getting chelseas sized right.

 

[bicycleradical]

I bought a pair of AE Liverpool Chelseas about a month ago. My feet are pretty wide with a high instep and so far, this last suits me pretty well. I've spent a good amount of hours wearing the boots so far and am happy with how they fit and look. Being that I've bought many AEs, I was comfortable doing an online purchase knowing their lasts and how they fit my feet.

I think @Blastwice is right. It would be best to be able to try some on if you don't have a frame of reference.

 

[TimothyF]

Chelseas are like loafers and other laceless footwear: If you're buying RTW, it's best to try on in-store or alternatively know your exact size in a specific last/brand/makeup. If you want something that fits truly perfectly, you'd probably want to go with MTM for laceless footwear.

Wholecut patterns vs. non-wholecut will never make any practical difference from a quality/durability standpoint-- it's an asthetic choice, usually. The higher the price, generally the better leather. There are many good (more budget) leathers out there, but it takes a lot of experience to know which will look good over time and other qualities you might be looking for, so price can be a shortcut.

I agree w/ jack webb that Chukkas can be much easier to fit and a good alternative if you're having trouble getting chelseas sized right.

Already own a pair of chukkas, and at least 1 more pair of derby boots. I'm partly driven by the stigma that family members or peers take much shorter to put on their "lower quality" shoes, while I'm getting out my proper leather shoes and fiddling with the laces. I wanted something laceless like the Chelsea

And yes for my first pair I'm already limiting my universe to only what I can try on in person, which is a small number of brands that I can probably count with one hand

I may have a smaller-than-average heel. Do off-the-rack Chelsea boots tend not to fit those types well?

 

[kylepw]

In the Chelsea boot department, I feel SF tends to push boots like EG Newmarket, Carmina and C&J for craftsmanship and more-bang-for-buck reasons. Personally, whether you're going for chic or chunky, I think they are all aesthetically "*yawn*..." I have a pair of YSL Wyatt that look and feel incredible. Will they last 20 yrs? I don't know. My "chunkier" JM Weston Chelseas (which I also love) will likely outlast them. But together, they cover a lot of stylistic ground for me. Wholecut, hidden seams, etc. are all nice but if you aren't in love with the boot's cut, comfort, style, etc. why bother? If you find yourself in Paris, I'd check out Aubercy "Matt" Chelsea. I haven't seen IRL but looks like a nice balance between a sleek G&G and fashion-forward Wyatt.