simon crompton caliendo bespoke

A few of the pictures of me from Pitti this year. Above, in brown tweed Caliendo jacket (more on that in a couple of weeks), Anderson & Sheppard flannels and Ralph Lauren madder-like orange handkerchief. 

Tweed such as this goes well with lots of colours, but particularly autumnal ones such as burnt orange and dark green. The navy tie (just in shot, from Viola Milano) anchors the outfit. Its grenadine texture and the madder of the hank are both better with casual cloths such as tweed, for me, than regular silk. 

simon crompton pitti

Anderson & Sheppard flannel suit, dark green Isaia tie and cream handkerchief with lime-green edging from Lissom & Muster. Tan bespoke oxfords from Gaziano & Girling (again, detailed post coming soon). 

This jacket has the narrowest wrap-over of any DB suit John Hitchcock cut for me – 3.5 inches – and I specified it for all subsequent double-breasteds. It has all the advantages of a narrow wrap, such as a larger gap for shirt and tie, but is far enough away from the trendy one-and-a-half-breasted jackets at Brunello Cucinelli and others.

simon crompton pitti

With Tommaso of Stefano Bemer, with whom we always stay. Note the roll of the shirt collar around my tie. I asked Luca of Satriano Cinque to lengthen my button-down collars slightly to achieve this roll, and it means the shirt works both with and without a tie. Otherwise the button-down lies flat and rather lifeless when fastened. Shoes are Edward Green Top Drawer.

simon crompton pitti cape

Trying another version of Miguel’s Portugese cape. A better colour than the brown I tried before, and a better size (the smallest) but still a little too extravagant.  

Other pictures around the net, including on Thousand Yard Style, Manolo and Pitti Immagine on Instagram.

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Simon – great photos and the brown caliendo looks superb. I must admit to copying the brown / grey / blue approach this evening and managed to get approval from wife and teenage daughter! Many thanks and regards….D


I cannot but notice the absence of turn ups on your pants. What is the justification of this personal preference? Nonetheless, both outfits are marvellous.


i have never been a fan of the db suit, but I think that one has converted me

Tom Williams

The Caliendo jacket is truly beautiful. Might I ask, are the accompanying flannels bespoke from A&S or from their haberdashery?


Great photos Simon!

Question, is the heel on that G&G slightly higher than normal?



Re: Mike and his disdain for the double breasted jacket seen here – I saw it and immediately thought, ‘I want the same dove gray flannel DB, but from Cifonelli, featuring large, eye-catching, upswept lapels!’

Can’t please everyone – gorgeous suit, Simon!


If it wasn’t for the collar, you could pull off that cape… Only in a bleak winter though…

James Cox

Dear Sir,
A 8×3 double breasted coat with same overlap and buttoning stance would look better on the flannel coat, in my humble opinion. Such short overlaps give the advantage of shirt show on more button configurations.

Yours Truely,
James Cox


The cape is “Portuguese,” Mr. Crompton; not “Portugese.” Great blog.


On the A&S suit, by wrap-over are you referring to lapel width? Can you elaborate on this differnce as it seems to have a pleasing effect.


That brown Caliendo jacket is everything!


Wonderful! Love your leather brief as well. Bespoke?


That brown caliendo jacket looks so rich and has such depth of color and texture that I’m writhing with envy.


Like the brown Caliendo, Simon!

Could one wear a brown flannel jacket with grey flannels or would that not work?