A Bespoke Balancing Act

Ordering clothes can be, for all its pleasures, a slightly stressful process. Except for those with bottomless pockets, each order is a decision that needs to be maximized in myriad ways. Navigating the balancing acts of fancy v. practicality and arrogance v. uselessness is no easy task, but here is the little I have learned on my relatively short journey.

I have been lucky enough to be able to order a few suits, shirts, and shoes these past few months in various degrees of custom and bespoke. And every time a measuring tape is thrown over my shoulder blades and the swatches in cloth books begin to fly, I start questioning and learning.

There is an impulse when you first start out to go for bare bones basics – plain grey and blue suits of exceedingly conservative cut. But that can be just as misguided as jumping right into the bright pink dupioni deep end. You need to order clothes that still have a bit of you in them.

It can be little things. Gauntlet cuffs, a particular pocket configuration, or the style of trouser straps that let you know at every moment that the garments are really, truly yours. When you balance this with an otherwise traditional foundation, you get the best of both worlds – clothes that are classically you.

If you don’t, and instead build a wardrobe of entirely bland basics, when you finally have all the basics covered and can get to the “fun” stuff, you’ll have a closet full of clothes you don’t really like that much. And doesn’t that defeat the whole purpose?

There is also the dialogue aspect of ordering custom to get used to. There is a weird feeling when you get in the fitting room to just let the tailor do his thing, but he needs you to speak back. The romantic notion of bespoke being a collaboration is no fiction; if you don’t guide the tailor he can’t give you what you want.

However, when just starting out, there are things your tailor will know that you will not, no matter how much time you spend looking at clothes online. You want to trust him on technical things, while giving him feedback on what you do and do not like. Obviously you don’t want to be an ass, but acting the shrinking violet is no help to anyone.

Ultimately, I’m very early in my journey. That’s the real pleasure though. Building a wardrobe along with a series of friendships and lessons about yourself is something that no amount of shopping can offer.