ASK NICK SULLIVAN: Letters To Esquire's Fashion Director, Answered by Zac Little

I'm turning 40, and I have the opportunity to choose a watch as a present from my family. I'm looking for one that can be worn on all occasions and that I can one day give to my son. I like the Omega Seamaster ($3,870) and the TAG Heuer Monaco ($2,270)—any other suggestions?

Bennie Rheeder, South Africa

Do you really need another memento mori at this point, Bennie? Look, you're going to die someday. A watch you pass down the generations won't change that. In fact, between now and the time you give it to your son, that fucking watch will only make things worse. You'll look down at your wrist and see it tick tock tick tock tick tocking your life away. (And I know, I know, they say a watched pot will never boil. But it will! I've conducted a series of experiments.) That goes double for the TAG Heuer, which can actually calculate your life expectancy with 94% accuracy. So I guess what I am saying is, if you MUST, go with the Omega. Those fuckers at TAG are crazy.

I have a great black suit that fits me like a glove, but I sat down on an iron patio chair and somehow ripped a small hole in the slacks. I'd like to get a new pair of pants to match the jacket, but my tailor said there's no way I could match the jacket perfectly and that I'd be better off getting a contrasting pair of slacks. Is this true, and if so, what color slacks should I wear with the black jacket?

Sean Olson, Greensboro NC

Sean, haven't you seen that Mentos commercial where the guys sits on the bench and it's covered in wet paint and so he gets stripes on the back of his suit so he rolls around on the bench and makes it pin-striped? What I'm saying is: MAKE LEMONADE, DIPSHIT! Get the most out of that hole! (I copied and pasted that last sentence from my sex advice column; works in this context, too!) Make a bunch of matching rips in your suit and hit the town, head held high. You're on the right track, baby. You were born this way! I'm not sure how that applies here, but whatever.

I am looking to get a pair of boat shoes, but I'm not sure when and where it is appropriate to where them. Should I go with “drivers” instead?

Lucas Provencher, Portland ME

I can tell I'm not going to sell you rich douchebags on the versatility and staying power of Chuck Taylors, so I guess what I should tell you is when in doubt, consult Kanye lyrics. From "See Me Now":

I’m in a speedboat in my boat shoes, ha!
I swear my whole collection’s so cruise
I might walk in Nobu with no shoes
He just walked in Nobu like it was Whole Foods!

What did we learn? Boat shoes are for speedboats. Kanye has a lot of shoes. He has so many shoes, sometimes he doesn't wear any at all. Maybe try that? I mean, as long as you wear the Dior Homme Skinny black suit (in accordance with Kanye's Rosewood Movement) at all times in public, people might not even notice you're barefoot. Or maybe Kanye West is crazy? I'm not sure what to tell you.

As a bow-tie wearer, I find your suggestion in the June issue that a pre-tied bow-tie is acceptable abhorrent. I say grow up, be a man, and learn to tie a bow.

Joseph B. Khoury, Lynchburg VA

I find the construction of your first sentence abhorrent! But anyway, I'm a little lost, because you're writing from a place called Lynchburg and using an irritating phrase like “be a man,” so at first I'm conjuring the image of an old, hateful, rich white guy watching his grip on the aristocracy slip away to the likes of the Rosewood Movement. But then I realize your last name is Khoury, and suddenly I'm thinking I'm dealing with a militant black Muslim. (What are you doing in LYNCHBURG, Brother Khoury?) Since we're talking bow-ties and general condescension, you could be either! Hmmmmm. Well, at any rate, I'm going to start telling people that a self-tied bow is for gays only. That way I'm guaranteed to piss both potential versions of you off. How do you like me now, Joseph?

Previously: "The same governing principle applies to balls and penises."