Not sure if you should wear that Tommy Bahama shirt out tonight? The magnificent bastard is here to help. Go ahead. Ask away.
Q: I met a man at a party and he was impeccably dressed in a charcoal suit and black tie. We have been seeing each other and he dresses very well; however, he has let it slip that he wears a Tommy Bahama watch and thinks that J. Crew floral shirts are acceptable "during vacations." Should I give him the benefit of the doubt, or kick him to the curb? Thanks for the help.
A: Katelin, the Tommy Bahama watch is definitely a red flag but you could fix that problem by buying him a watch for Christmas. There are still 4 days left. Regarding the floral shirt, they're OK during vacations in Hawaii.
So he's warm. And remember, as Tom Brady clearly demonstrates, many MBs are made, not born. We say give him the benefit of the doubt. If you look at our graph of the American male below, the vast majority need work and with your help, this guy sounds like he could be on the verge of breaking through.
Q: My aunt and soon-to-be uncle have chosen the following dress code for their wedding:
"Nice shorts or slacks and Aloha/Hawaiian shirt and flip flops or comfortable shoes."
This might be the most un-MB thing I have ever heard. Do I have ANY options? Other than disowning?
A: Suck it up, complete the outfit by draping a camera around your neck, and send us photos. We want to see the bride and groom's matching Hawaiian garb.
Q: What's an MB's breakfast drink? Mimosas seem unbastardly, so what are we to have with our mid morning breakfast when we're sailing in Hawaii?
A: Tripp, a few thoughts:
1. Mimosas are for women.
2. While we've given lukewarm special dispensation for Tommy Bahama camp shirts while on the Hawaiian Islands, we don't for Hawaiian Island-y cocktails while you're there. Continental U.S. cocktail rules still apply: no blenders, no pastels, no straws, no flowers, and absolutely positively no umbrellas.
3. Make it a Bloody Mary. And easy on the bloody.
via Village Hat Shop. $53.00.
Q: I'm heading to Hawaii in a couple of weeks (for leisure) and I'm starting to think about what to bring. Keeping the luggage level to carry-on is a must, but I need to pack a hat. Where can I find something that could pack easily, but wouldn't look like I'm looking for the nearest trout stream?
A: Joe, you're really visiting Hawaii in July? Can you reschedule for January? Either way, a hat is a good idea and a brand we really like is Block Headwear. They really get the "classic with a twist" aesthetic we dig. Several of their spring/summer straw hats are crushable, like the Degas fedora. (And their tag can easily be removed.)
(See previous posts on Hawaii travel.)
Avoid Looking Like This Guy
Q: OK, I have to attend an insurance industry convention in Hawaii. The "code" is resort casual. I can already tell, to fit in with this crowd I'll need a few expensive Tommy Bahama camp shirts. But it's not my style. It actually screams "Hey, I'm so stupid that I would pay $120 bucks for 1 shirt." What would you do? Go against the trend, or try to fit in?
A: A few thoughts:
1. We're glad it's not your style, though you cannot be afraid to spend $120 on a shirt you like.
2. We've previously stated our view on Tommy Bahama camp shirts. Yes, they are permissible on the 19-island/atoll archipelago known as the "Hawaiian Islands."
3. Hmmmm ... "go against the trend or try to fit in?" If you're an aspiring MB, what would you guess is our recommended approach?
4. We've previously offered suggestions on how to do Hawaii right.
Q: I will be in Hawaii for a week for the first time in some time. My wardrobe has few to nil summer or warm weather components. To ensure a great vacation free of ransom-worthy toolbag photos, can you provide some recommendations for me so I can snatch up some MB-worthy clothes for the island sun?
You mean you don't want to look like this guy? Good move, indeed. Even though MB.com lukewarmly sanctions Tommy Bahama while in Hawaii, avoid it. Instead, keep it casual and understated with these loose John Varvatos Soho pants (middle), and this perfectly rumpled J. Crew broken-in pocket jersey polo (left). Then, throw in a dash of zip -- and a subtle yet meaningful nod to surf culture -- with these plaid Volcom flip flops.