I’m a bit obsessed with monogramming at the moment. Tasteful monogramming, that is. Unfortunately, this act of labeling what’s yours is often abused as a pretentious display of wealth, but if kept discreet, it can be quite cool and classy. For button-ups, I prefer the initials to be below the shirt pocket or on the tail of the shirt. For sweaters/cardigans, the spot of choice for me would be again on the bottom where the waistband is. To prevent gaudiness, the thread should be matched closely to the color of the piece that is being monogrammed. Most retailers of fine menswear offers a monogramming service, but for those of us not buying custom fit shirts, J.Crew also has its own Monogram Shop (pictured above). For $10 extra, they will pretty much monogram anything in their men’s store (jackets, shorts, everything – even boxers). Please ignore the bright orange initials paired with the neutral gray/blue tie. It’s breaking the rule of subtlety, and as I’ve already said previously, I don’t want to be that guy.