Tim Little bespoke boot chelsea elasticated

As mentioned back in October, I recently had a pair of bespoke Chelsea boots made by Tim Little – the owner of Grenson shoes, who also runs a smaller label under his own name.

I was interested in Tim’s bespoke offering primarily for the cost. At £1950 (and £900 for every subsequent pair), it is much cheaper than the other, better-known makers in London. This is partly due to the small, occasional nature of the bespoke business, and partly to the quality of the materials and finish.

The hope, therefore, was that this could be a bespoke option for anyone looking for a bespoke fit without all of the aesthetic details.

That hope, I’m pleased to say, has been largely fulfilled.

Tim Little bespoke boot chelsea fit  

The boots are tan Chelseas with an extra-wide elasticated section. During the fitting process, it became quickly clear that I needed this addition to deal with the proportions of my feet: relatively wide, with narrow ankles.

The fitting (we only needed one, but there can be two) was good in many ways. The front of the shoe was perfect: nice chiselled shape, with just enough room for my toes to move comfortably. The shape through the back seam was beautiful: given my narrow ankle, that line up the heel and into the ankle had an exaggerated curve. And the instep was fine: it needed some excess taking out of the arch, but only a little.

There was one problem though. I couldn’t get them on.

The boot fitted perfectly for the foot and ankle, but didn’t allow enough space to get the former through the space for the latter. 

Tim Little bespoke boot chelsea sole

We cut the elastic in order to get the boot on and assess the rest of the fit. Then we calculated how much the elastic would have to be enlarged.

When I picked up the boots, it was, frankly, still a struggle getting them on. But in the weeks since the leather has softened up, and they are now perfect. Tight enough to make sure the foot is held and doesn’t slip forward, but loose enough around the joints and toes.

As to the look of the shoes, you can see from the images here the lovely colour of the leather and the solid make, including a nice, trim welt. While both the welt and sole are hand sewn, however, the waist is simple and square. There is no bevelling or tight cut to the upper as you would get with Cleverley, Gaziano and so on (although not with John Lobb).

Tim Little bespoke boot chelsea

The fit through the ankle has already been mentioned, but it is also nice how the fit through the arch was improved after the first fitting. You can see that attractive curve along the inside of the shoe in the image above. This level of fit was particularly interesting given that Tony Botteril (the measurer) uses Springline to make the bespoke last, rather than an internal lastmaker.

Elsewhere on the quality, the leather of the upper is good, but not quite as fine as other bespoke makers or high-end RTW such as Edward Green. (This is most obvious in how it polishes.) And the three-piece shoe trees that we made were rather too big; but we can correct that later.

Overall, the boots were great value and I’d highly recommend to someone looking for a bespoke fit at a more affordable price.

Tim Little bespoke boot chelsea3

Photos: Jack Lawson

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Nice boots, though the creasing is quite extreme.


The shoes are set off beautifully by the colour of the dog. Good choice (of dog!).


Hi Simon,
These are lovely boots indeed! They would be very suitable for travel from Autumn through Spring. But I just wonder why you have chosen tan as to their color. Burnt pine could have made them far more versatile, I guess.



Whilst I appreciate the bespoke nature, they are in essence a casual boot. Whilst the last is important as you have found it is the sleeve and ankle fit (and access for the foot) that is paramount. Manufacturers such as RM Williams have perfected this aspect over decades. The other big difference is that the upper on an RM boot is whole cut with no seams for a better fit, and the upper, as with bespoke is preformed. The sole is Goodyear welted. One of the classics is as linked above, in brown suede. Whilst in many aspects bespoke can be king, there are some aspects of apparel wherein quality lies in heritage (and thus maufacturers experience), albeit that it might be RTW.


Simon, all I`m saying is that you spent £1900 on a pair of boots that wouldn`t go on your feet without alteration. That speaks of a problem both with design and experience. RMs are not bespoke but in specialising in this one area they have learnt a thing or two over the years. Grenson have specialised in traditional English shoes (I bought my first pair in 1984). This is the key aspect of what I`m driving at. Sometimes, to create a classic design, tested by time, techniques can be learnt which can and should inform bespoke. For example it is worth looking at RMs preforming techniques which stop excessive creasing and roll-back of the upper. In the end we can all learn from each other.


I’ll have to agree with Stephen on the RM comment. With various levels of exotic skins available (from camel to ostrich and croc) their MTM service for widths, toes, heels etc is brilliant. The single skin and only one seam also means that the boots do become the most comfortable pair of shoes you will own.


Hi Simon, another great post. I particularly like the way you explain the collaborative process between customer and maker. In my experience the bespoke process very rarely (if ever) produces the perfect garment (or item of footwear) – it’s just very rewarding from a design, fit and comfort perspective and also enormous fun! I would be interested to see what the results would have been if you’d ordered your tan chelsea boots from a number of different makers and then examined the contrasting results (although ten pairs of tan chelsea boots may have been a touch OTT even for you!).

Eric Rytter

Simon — question for you: in the first picture it appears that the elastic has begun to “ripple” toward the top. I have a very similar pair of TL chelseas from about 10 years ago, which I love, but the same has happened to them (perhaps because of similar foot proportions to yours). What are your thoughts about this? Anything to be done about it, or is this just to be viewed as part of the “patina” for chelseas that comes with age and wear?


sorry — modifying name: should have just used first name.


Hi Simon which shoe polish brand(s) would you recommend?

Jodhpur lover

Dear Simon,

Why don’t you want thicker soles like the RTW Trickers Jodhour boot?

Don’t you think replacement of the elastic is complicated in every way for the repairer of your boots?

Why tan, why not acorn?

Paul Weide

Hi Simon – could you specify? Saphir in light brown? I ask because I am reluctant to purchase shoes that look magnificent, but are “antique tan”–and I worry that I won’t be able to keep the color.



I’m looking to buy a pair of tan suede Chelsea boots with a Cuban heel. I found a pair on David Preston’s website although they were black http://davidprestonshoes.com/product/lexington/ but they have sold out and aren’t restocking.

Can anyone suggest a place I can buy such boots for that sort of price? £100-£180. I was inspired by a pair of Saint Laurent boots but they’re out of my budget.
Perhaps someone can suggest a boot maker in London?


No Cuban heel please!!!!!!!!


Ignoring the response above, any suggestions are very welcome! Still on the hunt for these boots



I think the post above may have been a little dismissive but very curious as to why you search for a Cuban heel… If its a height issue I would argue its a little counterproductive, drawing attention to ones stature etc by such an article of attire. Otherwise I think they are a bit flamboyant!
Most bootmakers won’t do a cuban heel for those reasons, so you may need to go bespoke or settle for low quality.



I like the style. Most of Saint Laurent’s collection use Cuban heels:


I know an acquaintance who got a pair of bespoke suede Chelseas with a Cuban heel in East London but I can’t get the name of the boot maker. Any ideas?



Hi Simon

Afraid to say another vote here for the RMs chelsea boot. I’ve had a number of pairs over the years and they have all been beautifully fitting, beautifully made shoes. All hand made, and the leathers really are some of the best I’ve come across. There’s just no way I’d go near Tim Little or other bespoke when there is this sort of quality for ~£300. Just my 2p.


Hi Simon,
Could you give me more information about your comments on Tim little’s leather quality? what do you mean by their leather quality is not that good compared to EG or GC? I think they are using the same calf leather, right?




Thanks for your quick reply, Simon. how is the fitting compared with GC? (no need to consider EG,cuz they dont offer bespoke service.) You also commented in the post that Tim little is lack of detailed finish,“There is no bevelling or tight cut to the upper as you would get with Cleverley, Gaziano and so on” does it affect fit substantially? Put it in another word, what is the main difference between Tim and other well-known makers apart from the finish of the leather? i do care about the fitting.




Thanks Simon,
I have order a pair and will see how it goes.



Hi Simon,
I’m desperately trying to find wide fitting shoes and I’m really struggling. Sadly bespoke or MtM is out of the question cost wise. Can you advise at all?


Through the years have you been able to wear your various dress boots as much as you hoped? Although bespoke boot articles show you had keen interest at one point, when I see pictures of you Fall/Winter/Spring with cold and wet weather outerwear – you still wear dress shoes but rarely boots. Thanks!


I’m someone who loves boots (I have seven pairs!) and I wondered whether you might consider devoting an article to boots – perhaps covering the different styles, implications for formality and how to combine with clothes. I feel that the smart boot fraternity is under-served!
A personal boot retrospective along the lines of your Anderson and Sheppard one might be interesting.
All the best.


Hey Simon, what do you think are some pros/cons of chelsea boots that are slightly shorter than the standard chelsea height? Could this change the formality level/function of the shoes?


Cheers Simon, ill stick with the standard height then! For maximum versatility of the chelsea boots for semi-formal/casual and casual attire, do you have any advice on what color to go for? In your articles, you seem to promote dark brown for formal shoes – does this remain the same for chelsea boots?


When dressed casually, I normally wear chinos/jeans with polos/shirts/knitwear and blazers. In smart style, high twist/flannels with shirts/blazers. I think my trousers are fairly evenly split btwn dark/medium tones with the exception of one or two white/cream. Cheers Simon


How about the toe shape, Simon?

Lindsay McKee

If I was wearing Chelsea boots with a tweed jacket and say flannels or cavalry Twill / whipcord trousers; are turnups (cuffs) acceptable in these combinations?

Lindsay McKee

I’ve two bespoke pairs of trousers and they both have turnups.
I’m sure they’d look fine with or without the turnups!


Simon, what color chelsea would you go with for maximum versatility?


Thank you for your reply. See lots of men wearing black leather chelsea with mid color jeans, chinos and basically everything these days even in some fashion magazines- what’s your view on that?


Sorry I didn’t quite understand what you mean. Do you mean that black chelsea can be worn with anything except w/ warm colors?


Simon, what toe shape would you go for bespoke dark brown calf chelsea? And do you mind kindly explaining your answer please?


Also having commissioned many bespoke shoes for over a decade, would you commission a bespoke dark brown chelsea?