A Man of Many Hats (literally)


When my friends come to me and ask for style advice, a big concern is what style they should go for. They say, “Jack, I need to update my wardrobe. What should my style be?” My answer is always, “You don’t need to choose a style. Just choose style”. There are tons of looks out there, and I’m a firm believer in having more than one. In life, I consider myself to be a man of many hats – shouldn’t my style reflect that?

 Style 1) – Work

I wear a suit to work everyday. Generally I’ll throw on a Hugo Boss or Zegna ensemble that fits great, and looks professional. This doesn’t mean I want to wear my work suit to Vegas with my boys. I want to step my swag up in the City of Sin. I’ll up the designer and the look, so instead of wearing my clean and classic, I’ll wear almost too small and dramatic, i.e. Tom Ford, Neil Barrett, or a custom made suit that my tailor cringes at when I ask him to make it for me. I need flair. I don’t want to look like the Average Joe from Jersey shore with my un-tucked collared shirt and faded blue jeans. He should have left that shit at home and stepped his game up; Like me. Why blend in when you can stand out? I want all eyes in my direction. You think I’m going to do that with a suit I went to an investor meeting with earlier in the day? Not happening. There’s a reason my tailor continues to make those suits for me – he knows they work.

Style 2) Beach Casual

I won’t wear a suit to the beach, unless it’s a night party and I have a waiter making me dirty goose martinis, Old Fashioneds, or Vodka Gimlets (in which case always go linen). Most of the time, I save my suits for impressing in the city. This is the beach and that shit doesn’t work in these parts. You need another kind of swag. You need to roll up in your drop top Caddy, and your tailored T’s. I hate shorts, but you’re at the beach so rock em while you have the chance. Just make sure they aren’t below your knee. Oh, and leave your flipy flopy’s at home (it’s either them or your style. You can’t have both). Bust out your ferragamo boat shoes or even your cream Chuck Taylors. Throw on your defunct pro team snapback, and Vintage Clubmasters and hit the beach. That golf tan’s not going to fix itself.

Style 3) Ball Room

That black tie wedding has come around and you need to be back at your freshest. Keep in mind, your Grandpa is going to look his best also, in his traditional shawl lapel and satin bowtie, but you’re not him. You are you. You need to be original. You might ask yourself “How the hell am I going to stand out in a tuxedo when everyone else has on the same thing?” First off. Stop asking stupid questions. Secondly, they aren’t going to be wearing the same thing. Is your black polyester Men’s  Wearhouse suit going to be the same as my black super 180 Zegna three piece? Absolutely not. Same idea applies to this wedding. Everyone will have the same concept on, but yours is better. Yours has character. Yours has style. You don’t need to spend a fortune on a special tux either, you need to dress it up with multicolored pocket squares and maybe a matching bow tie. Hook your suit up with some bling like some gold or platinum cufflinks, tie clip, or tie bar. Also, get yourself a nice watch. Every man needs one (or 50).

On just three different occasions you went from Hugh Hefner,  to Paul Walker, to James Bond. As long as you choose to have YOUR OWN style rather than blend in, and throw in a bit of Swag, you can be whoever you want. You’re the man with many hats.

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