It's been a while since I've shared one of my many neuroses, but a recent purchase by one of San Francisco's most discerning customers has forced me to weigh in on a purchase of his.

Will Boehlke's blog, A Suitable Wardrobe, is a daily must-read for me and thousands of other men obsessed with clothing. For those that know how particular I can be about my clothing, Will has me beat by an order of magnitude. I have custom suits, shirts, shoes, and cufflinks, but Will would add custom ties, socks, suspenders, pyjamas, and other accoutrement to that list. He literally travels the globe to acquire exactly the item he needs to plug a singular, specific hole in his wardrobe.

So it was an honor to have him reach out to On The Fly when he was in the market for a new laptop bag. I shared many of my thoughts on the various business case options we offer, and he ended up with a stellar choice: Mulholland Brothers' Deerskin Slim Laptop (pictured). I could make a very strong case that this is the finest bag we have to offer based on style and durability, but I'll do that another day; Will's review is here.

Enough about Will; let's talk about my neuroticism. The death knell for Will's last bag was a broken shoulder strap, which we can probably all relate to. Except I never use a shoulder strap if I'm in a suit or sport coat. I think of a leather strap crushing the shoulders of a nice suit jacket or sport coat the same way hardcore animal activists think about eating meat: it's cruel and inhumane. For gentlemen like Will, who have personally met the tailors that will hand-sew their bespoke suits, the only thing that has prevented me from losing all faith in humanity is the hope that Will only uses a shoulder strap when sans coat. This isn't like putting ketchup on a Charlie Trotter steak; this is like walking into the freezer and grinding up the filet into hamburger meat. Decorum is the only thing keeping me from making references to clubbing baby seals.

I understand the enormous benefits of the shoulder strap, and I use one regularly with my weekend bag when not wearing a suit or sportcoat, so I'm hoping that Will just wants the option to attach the shoulder strap when he's dressed more casually (note: that is a relative statement since casual dress for Will is a two-piece suit).

In all seriousness, though, if Will says a suit will survive a shoulder strap, I may need to consider getting over this particular neurosis.