3.02.2013

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

Is wearing an undershirt necessary when wearing a dress shirt? I really don’t like seeing the outline of my undershirt under my dress shirt. –Bryan Erskine, Fountain Valley CA

Ah yes, the age-old “upper commando” question. Ruling out the possibility that you’re a chimp who was raised as a human and this discomfort at being civilized is the beginning of a series of revelations about the true nature of your past, I’d advise you to deal with it. A little wife-beater show-through is kind of charming, no? It’s at least more charming than your weird nipples. Who invited your weird nipples to the office, Bryan? That’s right: nobody. So keep the salami slices in the deli paper.


I’m a middle-aged guy going on a cruise, and I need to wear a jacket and tie at dinner each night. What do you recommend? Steve Volkman, Vancouver WA

First of all: what kind of jerkoff Dixiecrat bullshit cruise is this? You have to wear a jacket and tie at dinner? Not a mustard-stained Acapulco shirt, as God intended? WHERE DO YOU GET OFF, VOLKMAN? (I’m honestly asking. WHERE DO YOU GET OFF AND WALK AROUND FOR 2 HOURS REC AND MEAL TIME?)

If I were you I’d go to dinner in just a jacket and tie, nothing else, in protest of that silly policy. But I’m not you—and THANK GOD for that, you wouldn’t catch me DEAD on a cruise line, especially given recent events. In fact, I suggest you wear a toilet paper jacket with a tie made of insulin bottles. It very well might come in handy.


I’m entering my second year of grad school. Can you get me started on a professional-looking wardrobe within a tight budget that’s both comfortable and a little casual? I’d like to get a few blazers, but beyond that I’m clueless. Matthew Marant, Lafayette LA 

Well Matthew, it really depends what you’re in grad school for. If it were business, you wouldn’t be asking me. You’d already have some bizarre older male mentor from a previous or current internship—one who took you out to dinner and told you how to order your steak, who showed you how to dress and even bought clothes for you, who brought you to the sauna on Fridays and had angry sex with you in the locker room (but not in a gay way. In a “business insider” way). And if you were in Law school it’d pretty much be the same deal, except you’d go to the sauna on Thursdays.

So, what is it then? How could you, at this stage in the game, still be unclear on what was expected of you in the professional realm? Oh fuck! Matthew, are you majoring in… the humanities?! Dear god. Well, you can skip the blazer and invest heavily in pajamas, then.

I am a 23-year-old student and I will be attending my first engagement party. The dress is “cocktail/casual,” and I’m not sure what that means. Thomas Evers, Athens, GA 

Well, let’s get a little more specific here. What exactly is your context in this whole engagement milieu? Did you have a brief, torrid affair with an older woman the summer after you graduated college? Is she, now dating a more age-appropriate man, inviting you to her engagement party as some kind of either conciliatory or passive-aggressive gesture? Are you not sure how you feel?

Or, is it a shotgun wedding? I’m saying, did your wildest friend’s sexual misadventures finally catch up to him? Did he knock up the judge’s daughter, say? Are you and your crazy pals trying to have one last hurrah before adulthood and solemnity comes a-knocking, perhaps?

Or is one of your parents engaged? Is this perhaps a second or third marriage for your father, or mother? Are all of your family tensions, long simmering, about to boil over?

To put it another way: is this your first novel, second novel, or an essay collection?
  • First novel: Wear a linen suit, dress shirt with no tie, and a colorful pocket square.
  • Second novel: Wear a tuxedo t-shirt and jeans. 
  • Essay collection: Wear all black, and don’t forget to put a digital recorder in your pocket. The New Yorker fact-checkers are no joke.
I was taught that my leather (belt, shoes, etc.) should match. What’s the score? –Mark Holk, Barnes WI

You are correct sir! The SAME COW law of men’s fashion is one of the oldest, and therefore most prestigious, rules. (The US Senate rules are mostly based on the first edition of Esquire’s Blackbook—the Spring 2013 edition of which is in stores now!) Of course, it’s pretty hard to be sure that your belt and shoes match EXACTLY, but DNA testing is getting cheaper every day.

In THE KING’S SPEECH Colin First wears a necktie through most of the film and leaves about a half inch of the shirt showing. Was this the style of the era or a quirky personal statement? –Michael Monroe, Bellevue WA

Firstly: SPOILER ALERT, dude. Secondly: that was your takeaway from the movie? You didn’t learn about overcoming adversity and rising to meet your destiny? Focus up, Monroe! Thirdly: Colin Firth. That man can wear a sweater, huh? Fourthly: what do you think I am, some kind of fashion historian? Fuck you.