Chris Despos – World Class Tailor in Chicago

On Chicago’s Oak Street, in an unassuming third-floor office space nestled in amongst the usual-suspect brands, you’ll find Chris Despos.  There are no racks or cases of “luxury” products.  Just bolts of cloth, spools of thread, and drawers of buttons.  And with these building blocks, Despos is making some of the finest tailored clothing in the country.

Talking about “this country” is actually a little misleading.  Despos is a truly world-class tailor.  After speaking with him about his customer interactions, making techniques, team of tailors, and seeing his finished garments, I’m willing to say his stuff is up there with the best in London, New York, Paris, and Milan.

Chris himself is usually soberly dressed – a striped suit, geometric patterned tie, a soft blue shirt, and brown shoes.  He’s not brash or in-your-face, but he is friendly and excitable.  He’s a true craftsman who lives and breathes tailoring, and if you get him going about the shaping of a shoulder or the concealing of side-seams, his eyes light up and you can tell it’s the sort of thing that keeps him up at night.

It doesn’t come as any surprise that his father was a tailor and he started working in the family business while still in high school.  All in all, he’s been working as a tailor for over 40 years now.  First it was with his father, then under a variety of mentors, and finally, out on his own.  “A girlfriend’s father asked me to make him a few pairs of trousers and I walked into work the next morning and gave my two weeks’ notice.  It was kind of bold,” he told me.  Bold, but it worked.

He’s now looking at over three decades on his own, almost all of which with the same team of makers.  These first stages of his career took place in Dallas (where he still keeps a shop and visits frequently), and on moving to Chicago ten years ago his tailors wanted to stay with him.  So, the garments go back and forth between Oak Street and the Lone Star State as needed.  Chris tells me the team he works with are the key to being able to do what he does – without a good, reliable team of top-quality makers he wouldn’t be able to produce garments at this level.

Two things distinguish Despos from the other tailors at his level: his cloth preferences and his shoulder.  Many tailors prefer to work with heavier cloth and find the light-weight stuff a pain.  Despos revels in it.  From his clients requesting it so often, he’s gotten used to working with lots of 9/10oz worsteds and can manipulate them like most tailors manipulate a 13oz flannel.

Now for his shoulder.  Despos likes to call it a “soft-structured” shoulder, and I think that’s a pretty accurate description.  It’s not an Ivy-league totally natural shoulder, but it’s nothing like a British military shoulder either.  Visually, it keeps shoulders from being sloped and slouchy, but manages to look like a natural shoulder.  On the body it’s light as a feather and feels almost like there’s no padding at all.

They key to this shoulder is it’s anchoring point.  It sits close to the inside of the collar bone, and the canvas and padding are shaped to act like a hinge.  It keeps the shoulder flat when you move your arms and makes the whole coat more flexible.  You can see in the above image how the seam, which isn’t actually stitched on a curve, bends smoothly with the natural line of the shoulder.

While, as I said above, Chris is a true craftsman in every sense of the word, he also appreciates how his work affects people.  He’s not just making clothing for clothing’s sake.  “The greatest complement I’ve ever been given was from a customer who isn’t particularly into his clothes.  He came up to me one day and said ‘Chris, you know that checked suit you made me a few years back.  That’s still what I put on when I need to feel my best.’  That’s what I’m about.”