The Glorious Creativity of Boring Clothes

Some female friends were discussing this piece from Harpers Bazaar about an ad agency art director who decided that she would solve the problem of what to wear to work by wearing the same thing every day:

As I arrived at work, my stress level only increased as I saw my male creative partner and other male co-workers having a "brodown" with the new boss as they entered the meeting room—a room I was suppose to already be inside. I just stood there—paralyzed by the fact that I was not only late, but unprepared. And my sweater was inside out. I had completely stressed myself out, and for what? This was not the first morning I'd felt this unnecessary panic, but that day I decided it would be the last.

The frustration I felt walking into that meeting late remained with me. Should it really be this hard? I knew my male colleagues were taken seriously no matter what they wore—and I highly doubt they put in as much sartorial time and effort as I had. But gender issues aside, I needed to come up with a solution to simplify this morning struggle.

I have no clue how the idea of a work uniform came to me, but soon, the solution to my woes came in the form of 15 silk white shirts and a few black trousers. For a little personal detail, I remembered my mother loved to put bows in my hair as kid, so I chose to add a custom-made black leather rosette around my neck. Done. During the colder months, I'll also top my look off with a black blazer. I shopped all the pieces in one day. It burned a hole in my wallet to say the least, but in the long run, it has saved me—and will continue to save me—more money than I could imagine.

Of course, there's a whole group of people who have removed most of the creativity from deciding what to wear to work, we call ourselves men. But by going with a truly identical outfit everyday she's missed out on the key to male workplace dress, which is having a fairly rigid set of rules as to what you should wear while allowing very narrow outlets for quality and creativity.

So, how do you dress like a director of pricing analytics?

Three pairs of pants, plus a fairly new/dark pair of jeans for casual Fridays (jeans not shown because I'm currently wearing them):

Eight dress shirts (sporty types wear golf shirts on Fridays, but I don't play golf and don't want to be a poser):

I could honestly get by with just one or two pairs of dress shoes/boots, but I kind of like them. And MrsDarwin bought me the boots for Christmas. (Never wear black shoes with a brown belt or brown shoes with a black belt. Just don't.)

There are doubtless a few combinations here which would not be a good call, but overall we have [4 pants] x [8 shirts] x [3 pairs of shoes] = 108 outfits, all without every having to think hard about what to wear.

Who knew it was so fun to be dull?



Should you wish to be dull:

Joseph A Banks and Charles Tyrwhitt are affordable and reliable. They have constant sales, and (how can a pricing guy resist telling you this) you really only want to buy things on sale there as they're clearly building their cost/quality model around the sale price not the list price. Brooks Brothers is somewhat higher quality, but their sales are less often and not generally as deep.

Allen Edmonds makes mens dress shoes about as good as any you'll find. They're made in the US and can be re-soled by the factory when the wear out. But honestly, they're kind of embarrassingly expensive. The only real excuse I can make is that with decent care they can last a good 5-8 years, with occasional recrafting as the soles wear out.