Halloween always raises a tough question for men of style: How, exactly, do you dress for a holiday that is all about the clothes you're wearing without looking like you're trying too hard (which you probably don't want to be doing) and without looking stupid (which you probably will anyway). That's what we asked two young men who prefer natty suits, throwback details, and nice shoes for this week's Blogger Showdown. Justin Bridges, of Tucked Style, isn't much of a costume guy himself but still thinks men should dress up for the occasion. Whereas Austin Wong, from Why You Mad, already believes he puts enough effort into his clothing daily, so Halloween should be no exception. Below, the two men debate who has the better strategy for pulling something together this weekend, plus offer some practical suggestions for costumes that are both sophisticated and simple. Well, if you want to practice ruining your favorite suit. Discuss. —Kurt Soller

Justin Bridges: I don't consider myself a Halloween junkie, but I do think this holiday is a great excuse for men to not take themselves too seriously. Costumes are a great way to pull your head out of spreadsheets and have some drinks while pretending to be something that doesn't even exist in real life. Or, for the not so adventurous, you can take on a look like James Bond's. Why not get laid along with all the free candy?

Austin Wong: You won't get laid again after she sobers up and realizes what's behind the mask. Not wearing a Halloween costume during Halloween is actually the ultimate costume. Sure, you stand out, but at least you don't look like you were dumb enough to spend $50 on a 100-percent polyester robe (that shit is not canvassed, pick-stitched, or even hand finished). Last year, I took the risk and wore the "ultimate costume." Some girl asked me what I was, and I replied "the best dressed one here."

JB: But guys who don't dress up are just afraid to express themselves. It's as if being outside of your norm is like traversing the Wild West. Men are too serious. So what, you look unpolished for one evening? Not going to kill you. The guys that seem to enjoy Halloween the most, anyway, are the ones that wear polos, shredded jeans, and flip flops on the weekend. Any costume seems like a better option than that.

AW: To be honest, I already feel like I'm wearing a costume among many of the men in New York. I realize we no longer live in the 50s and 60s, but everyone just seems way too dressed down these days. How is it acceptable that "dressing up" requires only one thing: a collared button-down shirt? Let's be real, most guys look like slobs year round. The only day they can really "dress up" is Halloween. I'm usually always a bit dressed, so I don't feel the need to change that.

JB: Yeah, you just have to be vulnerable on that night to the jokes that are bound to ensue. Maybe a man is too prideful to dress like a Teenage Mutant Ninja Turtle at the age of 26? Sure.

AW: At the end of the day, we who are interested in men's wear are always in "costume" (well, most of us). Not everyone has perfectly-fitted, light-padded Cucinelli jackets, or high-watered Thom Browne suits. We are the ones who are always "vulnerable," having paid our dues 364 days of the year. We are always out of the comfort zone. What is more abnormal than looking (slightly) normal on a day of abnormality?

JB: Yeah, men just want to be cool and collected at all times.

AW: Look, I am no Grinch of Halloween. If you really want to "do" Halloween, stick to the classics. Wear a mask over your best outfit, color-coordinate black and orange, or be Patrick Bateman for Halloween.

JB: Halloween is your time to put whatever you do on a daily basis — albeit slob or men's wear nerd — on hold for five minutes and get wild. I'm not a huge Halloween guy, but think of the detriment to the world if all we did was use this as an opportunity to dress up in better clothes? I'm definitely half asleep and slobbering right now because I can't get behind the idea of a bunch of Thom Browne and Tom Ford wannabes traipsing around.

AW: We can always incorporate our everyday items into our costumes. This strategy does, at least, save some money.

JB: I think the way to take the celebration and make it your own is to be quirky or funny. Show style via personality, not necessarily via wardrobe. For instance, I kind of want to dress up as Waldo, as clichéd as that is, but wear a sign on my shirt that says "Muh-f**** wanna find me!" A little rap reference, you know? Nobody says I can't wear a pair of Church's brogues with Hook + Albert red laces in them to match the shirt. There's nothing wrong with doing the best of both worlds. Be the best-dressed Phantom of the Opera, if you want. You don't have to wear a cheap outfit, and you can definitely pull the suit from your own closet, if you don't mind the chance of beverage spillage.

AW: Justin raises a very valid point. I fully agree that we can all can get into the holiday spirit one way or another. As for me, I will be in my regular suits — the "ultimate costume." More importantly, we all want to do one thing during Halloween and that is party. Happy Halloween. And, as Justin said, I hope everyone gets laid.

PLUS: The Esquire Guide to Easy Halloween Costumes, DIY Halloween Costumes, and Halloween Drinks and Cocktails >>

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