Asking the next question: An interview with Kirby Allison

Monday, September 2nd 2019
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I recently did this interview with Kirby Allison of The Hanger Project, as part of his Shoe Shine Sunday series.

It's a little bit meandering (and my shirt seems determined to reveal more chest than anyone would want) but I think there are some interesting points of discussion.

They include the relationship you build up with a bespoke artisan, advice on picking between tailoring styles, and how I started my journey, starting with London and then expanding to Italy and elsewhere.

We also discuss points around quality, such as how much quality variance there actually is in something like a tie, compared to a suit. That was the driving concept behind the whole of my Finest Menswear book, and it was nice to talk about it again.

I also personally like being able to expand on the themes of good writing and interviewing. Always seeking to delve a little deeper - and ask the next question - has always been core to what I love about it.



I hope you enjoy the discussion.

You can read more on the shoes I feature (and Kirby kindly polishes) in my review piece here on Stefano Bemer's Blue Bespoke service.

The jacket is my bespoke denim from Cifonelli.

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Nice video. One thing I usually dislike about dress shoes is how uncomfortable they are. When travelling or shopping, I usually wear sneakers, for the simple reason that with dress shoes I’d have sore feet in less than two hours and blisters in 3, whereas with skate style sneakers I can walk all day (yes, I’m aware it’s a discussable style, but it’s functional), which I usually do whenever in the city.
Is that any different with bespoke ones (said differently, can they match my sneakers in terms of comfortability)? Are there some specific points to pay attention to, such as the sole as mentioned in this video, to keep them comfortable and functional? Some specific makers you would both advise going to stay in that optic, and not an office / cab only shoe?
I would hate myself to invest that much money and energy into something that I won’t be able to really enjoy wearing and walking around with.


I annoyingly didn’t take your advice and now have a pair of EG where by heel moves about and it is really annoying (considering they are by far my most expensive pair of shoes!)
What are my options? I tried a leather patch in one but it only helped a bit…


Great thanks. Any cobbler in particular that is good in London?


Anonymous, it may not be my place to ask this question, but if you are buying an expensive pair of shoes, why not ask the salesman to observe if they fit you well or not?


True. I’ve had a MTO pair made by Gaziano&Girling, and the heel cup proved to be too wide. The G&G shop on SR listened, looked at the heel cup of both shoes and decided to have the pair back for a repair. Still have to wait for the outcome, but they’re in the factory now.


“…if you are buying an expensive pair of shoes, why not ask the salesman to observe if they fit you well or not?”

A good suggestion, but unfortunately there are a lot of people working at shoe stores – even expensive ones – who do not actually know how a shoe is supposed to fit.

Certainly, they’ll check your foot length and the width of your forefoot and see where your toe sits in the shoe. However, when it comes to checking your gait, the height of your foot (instep), the narrowness of your heel and other such details, the vast majority of shoe store staff would not have a clue and would not help. Just as with buying suits, it’s really up to the customer to get an idea of what suits their foot (or figure, in suits) and to check those things when they try on a shoe or a garment.


I used to have similar experiences as the original poster, until I learnt to start paying close attention to fit. Ensuring there’s no movement of the foot (no areas of rubbing) and not too much excess volume in the shoe (when stepping, causes the sole to bounce up and hit the foot which hasn’t yet reached the ground) addressed most of the discomfort in a dress shoe. It still doesn’t make it as comfortable as sneakers, but I’m good to be up and about on my shoes for 8-10 hours. If I want some additional comfort, adding a think foam insole gets it to sneaker-level comfort.


Well, that video is certainly a one-of-a-kind idea. Your “dear, close friend” (surely a stretch?) seems to be creating a riff on Jerry Seinfeld’s “Comedians in Cars Getting Coffee”. Except even it’s more strange and just doesn’t work IMO.
I don’t get the point – he should be interviewing you or he should be talking/showing how to shine shoes. Interviewing while shining shoes is plain odd.
Anyway Simon, a rare blip in an otherwise great blog….certainly feel free not to publish this if you think it overly critical or negative.

Peter O

That was quite interesting how an Englishman and an American exchange.
You both brought to the meeting a lot of experience and I found it exciting. I think shining shoes makes Kirby focused!



I have found that when you have the right size and last, dress shoes can be very comfortable once broken in, and the best fits, do not need much break in time at all. Also, with my boots from Alfred Sargent, Crockett & Jones, and Alden, in a bit of counterintuitive manner, the rubber soles are actually the hardest on my feet and back. They are generally heavier and have less flex to them. My double leather soles on Alden are the most comfortable, moreso that single leather, dainite, or lug (commando). I would have thought those would require a longer break in period due to the stiffness of the double thick leather sole, but it’s just the opposite. It’s a bit of a shock absorber. That said, there are several Alden lasts that fit well and several that don’t fit at all for my foot.

Good luck in your search for comfortable and smart shoes.


Instead of ‘Shoe Shine Sundays’ why not introduce ‘Flaneur to Flaneur Fridays’ ?
Each week Simon could interview a ‘Real Life’ flaneur about his life in clothes.
What was his journey ? Why does he dress as he does ? Who are his biggest influences ? What faux pas have been made en route ? What are his favourite pieces ? How and when does he wear them ?
‘Flaneur to Flaneur Fridays’ should, of course, involve only real people and not industry folk. Could be interesting n’est pas ?

Evan Everhart

I concur with Jason, most heartily in fact, regarding interviews with men of clothing (you could call it Men of the Cloth)! I would be most interested in, and amused by such a recurring column within yr regular blog.


Just to note that the shoe tongue pads you refer to, above, are available in the UK from Amazon.


Stretching the shoe topic but… I find buying loafers very difficult, I try my normal size and almost all are too tight. Each time to date I have sized up and then after 5-6 wears they suddenly feel loose but I am not brave enough to spend £500 hoping they’ll loosen up to be comfortable.

Dress shoes I have an even odder problem in that on any given day a different pair (I have circa 8 pairs) will feel more comfortable and similarly each and every pair can bite at some point but in different places on different occasions. Clearly it appears to be my foot changing rather than the shoes but really makes me reluctant to spend more than C&J handgrade… I did buy your recommended unlined chukkas but in 10 wears my little toe has created a bulge and the lining on both healcups have failed (though dont rub so have ignored)

Its in part this that has stopped me buying bespoke shoes even if I’d like to blow the budget for a single pair.

Robert Giaimo

I’ve tried insoles, heel and tongue pads and have had the most success with the insoles and tongue pads. Heel pads in general have not really worked for me, they tend not be substantial enough (in size and durability) and eventually breakdown with the rubbing of the heel. I’m sure this is a very personal experience as everyones feet and gait are different.


Yes, I tried them but a long time ago. I seem to remember their not sticking very well and being a bit thin. The fact that I am not using them now, suggests I was not very pleased with them. Ditto, the heel grips. I have never had any success with heel grips as they tend to come loose or wrinkle.

For two of my pairs of shoes, I am thinking of seeing if a cobbler can stick some leather under the tongues. A sure sign that things aren’t right in the fit department is that, when you do your laces up, the facings of the shoes are pretty much touching each other.


I don’t think you are showing too much chest. Why do you feel so? If you are not wearing a tie and depending how open the quarters of your jacket are, why not leave two buttons undone?

Ian A

In the past I’ve been far too cheap with shoes and suffered high street branded dressier types of shoes cutting through my feet like razor blades. I used to wear athletic shoes all the time as i’d All but given up, but one day thought i’d Push the boat out and get some Crockett & Jones and Edward Green shoes and wished i’d Bought them earlier in my life as they haven’t sliced all my heal up as others have.

Now I have enough dress shoes to last me the remainder of my natural life possibly 40 of years or so as I have well over 50 pairs of high end shoes.


Hi Simon, you recently mentioned a (sample) pair of shoes from Maslow So’s “Mori of Shoemakers” brand. Do you know whats going on there and will you cover those more in detail in the future? The pictures look great so far.


Thanks – Do you have any idea about when they will be ready, and on a related note, are you aware of any other Chinese makers that produce a comparable quality?

Paul Boileau

Curious concept. I confess I did not watch it all: did you tip Mr Allison at the end?
Perhaps it could be improved by employing more arcane methods; eg. if you were both boning the leather or using champagne a la Swann Club?


Simon, How do bespoke shoemakers handle orthotics in a fitting? Would they be able to build a last around them?


I’m aware that some bespoke makers that can incorporate elements of the orthodic into their last–so the orthodic is no longer needed since the shaping of the orthodic is part of the last.

I suspect you’d need to show your orthotics to a maker and discuss it to find out what they are capable of doing.

Andie Nicolas

Hey Kirby and Simon. Great video and learnt something from it.
However, I cringe when I see you (Kirby) flicking that polishing brush about wearing nice clothes. Perhaps a chef’s jacket or an artist’s smock might help in preventing specks of polish landing on your nice clothes?


Whilst there’s a common style for tailors in a particular city, there seems to be quite a bit of variation as you’ve mentioned (i.e. the drape cut on one end vs a more military structured one on the other in London). I wondered however, if there are ever, shall we say, ‘rebel’ tailors who break with the traditions of a particular city and offer something more distinct. For example, say a tailor focused on more structured jackets in Naples. In theory it could happen, but perhaps it’s just less likely to do so because such a tailor would be less succesful? On the other hand, perhaps the drape cut was in its origins perceived to be a break with the established style?