Pinstripe suits - gangster or banker?

I have a love-hate relationship with the pinstripe suit.

I like a few variations on the theme – chalk stripes definitely get me excited as a tailoring aficionado and Anglophile, but I also like a thinner, bolder stripe. I don't really go for them if they're wider than a centimetre, but of course, I take them on a stripe-by-stripe basis.

What I'm unaware of, in a modern context, is who wears the bold stripe? What kind of business person takes this option?  To me it's heavily weighed with gangster and criminal connotations, but is there a hierarchy I'm unaware of?  Is it your boss's suit or is it the wannabe's suit?

I tend to look favourably on the slim, rock star versions - a skinny stripe and even skinnier tailoring, lapels and legs cut to within an inch of their life.  Think The Strokes or Franz Ferdinand at the height of their powers, or Russell Brand levels of overt sexuality.  There's a louche appeal in the tailoring and use of pinstripes.  It definitely has a bad boy feel and this is probably what we all pick up on when considering the stripe. Sadly, this gets lost in the conservative shapes and silhouettes on offer.  The fact that we don't have the hips of a 12-year-old boy anymore doesn't help either, or that we wear them with such indifference thus losing the intention anyway.

Rather than the mob boss look - which has its own charm - the dandy rock star and the raffish layabout has the tip of my hat.  The slightly too small tailoring isn't for everybody, but worn a little short and with adequate insouciance, plus a crisp white shirt, it will have us all believing you're about to go onstage.

Check out English tailor Spencer Hart for an example of this formal nonchalance.  As always, a well fitting suit should be the goal. As I found out at the wonderful American Tailors recently, a beautiful, tailor-made suit from Naples suits my body type just fine. I can pull off the pinstripes and, regardless of my hip size - in my case the fact that I have them - it can work.

Finally, there's the chalk-stripe on a beautiful English flannel, which conjures up images of investment bankers and Fleet Street professionals. Instead of gangsters taking your money without you knowing, these guys do it with your full knowledge, but they do look sharp. The softness of the stripe definitely has an aristocratic, moneyed air about it.

Here are some tips to remember: Stripes should not match on your shoulder seam.  A correctly made pinstripe jacket (or any jacket for that matter) will be steamed and shrunk, manipulated and eased into place, any stripes that match from front to back panels is pure coincidence.  The fact that they don't line up is one of those beautiful quirks of tailoring, a badge of honour if you will. The extra width of the back panel provides a superior and more comfortable fit.  The same applies to the pocket jets. On the likes of Savile Row tailors Anderson and Sheppard these will be in perfect alignment with the stripe of the body but this is no easy task. It's also the reason why these suits cost as much as a small car.  Details matter.

From where I stand the pinstripe is OK, but I'd be interested to hear what you have to say about it.  Where does it fit into your wardrobe, if at all?

This article Pinstripe suits - gangster or banker? was originally published in The Age.