Q: So I have to attend this (outdoor charity) event for Mother's Day with my wife and son (2 yrs) where your entry ticket is this gaudy t-shirt that violates every known MB principle: logos, legibility, ugly, etc. My question is: since I have to wear this (I have to attend), is there any way to salvage it? Should I wear the rest of the ensemble as if I was wearing some other MB-approved shirt? Or would that just look too stupid (i.e. too much of a clash between MB-ness and clear toolbaggery) and should I just throw in the towel and just toolbag this all the way? Sorry for the short notice but I was just informed yesterday, and Mother's Day is just a few days away!
A: Rob, your mother probably once told you: Two wrongs do not make a right. Don't cave and go full-on toolbag. Even the ugliest event t-shirt can be mitigated and possibly overcome with the right ensemble. Since you are going to be very unformfortable on top, get very comfortable on the bottom with your go-to denim and sneakers (or sandals, if you've recently had a pedicure). Even if monsoons are predicted, add some vintage sunglasses to the look. They can block toolbaggery almost as well as UV rays, and will provide cover for pained facial expressions.
Of course, even with these tactics, you won't be able to forget the fact that you're wearing the shirt -- because you'll be surrounded by it -- so we also advise that you get drunk as quickly as possible. Skip the beer and go straight to the hard stuff.