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

When is it appropriate to wear a sport coat and tie versus a suit? I go for the “when in doubt, opt for the suit” statute. Do you have a simple rule of thumb?

Jon Carlock, McKenzie TN

In the future when you write to me I'd like your metaphors to remain consistent. If you have a statute, ask me to provide stare decisis from previous casework, not for a rule of thumb. Because I'm going to make like a tree and overrule you: When in doubt, do not wear a suit. Do not even wear a tie, unless it's a novelty tie! See, my personal feeling is that one can never be too casual; it's called the soft bigotry of low expectations, look it up. I mean, imagine you're taking a girl out to a fancy restaurant: The other diners are in tuxedos, you show up in an Ed Hardy shirt and a Members Only jacket. Who stands out like Antonin Scalia's thumb? YOU DO, baby! Only dead fish obey precedent, Jon. Fuck what you heard.

Is there a rule of thumb on how much you can have a suit altered? I wear a 37L. I'm pretty sure I can have a 38L taken in to fit me, but how about a 40L or a 42L?

Gabriel Lichtenstein, Los Angeles CA

The rule of thumb on suit alterations is that you can't have them altered so much that they have those thumb hooks on the sleeves that some hoodies have. They're comfortable, I know, but they're also kind of weird and make you look combative. Otherwise, I mean, I'm in full support of fucking with your tailor. Make them do whatever you want! Buy a fat guy's suit and take it in! Buy a child's suit and tell him to expand it! Have him cut a big hole in the back to "raise awareness about spina bifida"! It's your dime, and most of those dudes are assholes. So go wild! “Hey guy, I want this pant leg to stop a foot above the other one. Capeche?” Oh man, that would be fun to do and I'm going to try it sometime.

Why the reemergence of the button fly? It provides zero in the way of aesthetics, it's difficult to button and unbutton, and during the Chicago winter, it lets in the cold air. Thoughts?

Michael Gold, Chicago IL

You don't get an awful lot of blowjobs, do you Mike?

My girlfriend got me a charcoal houndstooth suit vest as a gift. I don't have the matching suit jacket. Can I wear it with a different colored (or even patterned) jacket? Also, can I wear it with jeans?

Taylor Hamill, Denver CO

I don't want to alarm you, Taylor, but I think your girlfriend might be an elderly gay man.

I have run into the ridiculous problem of getting holes in the crotch of nearly all my pants. Even heavy-duty jeans. Is my crotch acidic?

Eric Hafner, Kansas City MO

This is weird for me, because until now, in my head, everyone in KC walked around with their legs spread two feet apart, John Wayne-style. I mean, you want to have a strong center of gravity if you have to use your sidearm when you step out of the saloon, right? But clearly you must be walking around in such a way as to stress the fabric in your crotch region. This runs counter to everything I have been taught. Have you not been in a duel lately? Are you the saloon's piano player or something?

I am considering purchasing a dress watch—sleek and elegant but not too thin—and my budget is $3,000 tops. Any recommendations?

Jim Dickey, Charlotte NC

You fuckers with your watches! Have you seen these Wall Street protests, Jim? If you don't keep your head down, someone is going to literally kill you. How are we supposed to keep from eating the rich when they keep rolling themselves around in marinade? Holy shit.

Previously: "I don't want to be the Christian Bale to your Christian Bale's mom, but it sounds like you have some cunty friends, Krista."