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Debate: Why Are So Many Men Such Terrible Dressers?

There was a time in the not-so-distant past when a man wore a crisp white shirt and neatly tailored suit to the office simply to convey that he was of a certain means and self-respect.

But, oh, how fashion standards for men have fallen since those days. Many offices now allow male employees to stroll in dressed like they’re about to hit the skate park.

Which is, in some ways, a good thing. The loosening of arbitrary social norms is almost always worthwhile. But there’s also something to be said for putting time and effort into your appearance, and the confidence and respect that come with showing your best self to the world.

So why the hell don’t more guys dress better? To solve this mystery, MEL turns to its panel of a straight woman (Tracy Moore), a straight guy (John McDermott) and a gay man (C. Brian Smith), who find that men’s aversion to fashion is rooted in homophobia and laziness.

Brian: My grandfather once told me, “No one takes a man in shorts seriously.” So I never wore them to work.

John: I like the cut of your grandfather’s jib. There are like three acceptable scenarios for a man to wear shorts: beach, working out and temperatures above 85 degrees (and even then it’s debatable).

And his comment speaks to the larger issue, which is that fashion standards for men have decreased to embarrassing levels over the past few decades, and I hate it.

Tracy: I agree the standards may have decreased, but at a time when there is more advice and guidance than ever for men making an even minimal effort.

John: Most men don’t pay attention to that, though.

I don’t date or check out men, so I’m actually curious to hear how fashionable the male populace is.

Tracy: I see dapper, well-dressed men all the time

John: But you’re a coastal elite!

Tracy: I also see guys in beefy T-shirts and cargo shorts.

Brian: I tend to overdress, likely because I’m always nervous about looking too casual. It’s a horrible look for an adult man. Like, grow up, bro.

John: I’m with you there. And yet so many guys wear the basic bro uniform (ill-fitting jeans, generic button-down or T-shirt, baseball cap, sneakers over white socks).

Brian: Let’s say you’re going to a friend’s dinner party — is there a minimum requirement for a guy?

John: No, and that’s the problem.

Tracy: Yes, men have largely been given a pass (outside of formal events) to dress however they want, with no consequences. They often dress for maximum comfort and nothing else.

John: That wasn’t always the case, though. Used to be the only time you’d see a man in a T-shirt and jeans was when he was mowing the lawn. Perhaps I’m being precious, but I feel like something has been lost.

Brian: What would be a consequence (if there was one)?

Tracy: For the most part there is none. If a guy shows up to an event underdressed, some woman might privately push him toward dressing better, or his friends who are better-dressed might mock him.

A single guy who’s out on the scene and puts zero effort into his appearance might ruin his chances with more style-conscious women. But he still might get laid.

John: Doesn’t that double standard bother you?

Tracy: It bothers me enormously that men get to look how they look, and you don’t know what a woman “really” looks like unless you’re dating her.

John: What’s the lowest level of fashionability you’ll accept in a romantic partner?

Tracy: He has to have a sense of style I don’t find hideous. Cargo shorts and a beefy T-shirt is the main offender. Also, flip-flops.

Brian: I need a guy to dress like an adult.

John: What does that even mean nowadays, though? I wore jeans, a T-shirt and hoodie to the office today (and yesterday). I’m dressed like a middle-schooler. (See my point?)

Brian: Yeah, I didn’t say anything, but I noticed.

Tracy: But the clothes actually fit you. Style isn’t about the items themselves — it’s about design, fit and fabric. You have a style that isn’t off the rack of a Costco (sorry, Brian).

Brian: Kirkland-chic?

Tracy: Anything can be pulled off if it fits you and expresses some kind of cohesive style. It’s just usually men do nothing — absolutely nothing.

Brian: Define “cohesive style.”

Tracy: Style, like being cool, is just having some original way of putting things together on your body that works. Men could just buy clothes that fit and that would be a great fucking start!

John: But so many guys don’t!

Tracy: We could find a million men in ill-fitting jeans; oversize T-shirts and shoes that fell off a garbage truck. And that man will be like, “I have a lot of love to give! Someone should fuck me!” A woman looking like that would preemptively burn herself at a stake (and apologize first).

John: Problem is that most boys are never taught how to dress — that would be gay. There’s an element of homophobia to this.

Tracy: Absolutely. Trying too much, caring about how you look, is “gay” to so many men. So it’s almost like they pathologically go the other way

Brian: It’s just laziness. I smear mustard on my shirt often and I hate pussy.

Tracy: Because you are taught from birth that how you look doesn’t matter. Whereas every woman is told if she just covers this up, squeezes that and slaps a coat of paint on this, someone will love her (maybe).

But there is a stereotype that all gay men are somehow meticulous dressers. But that can’t be true. Some gay men probably don’t care, right?

John: Was your dad well-dressed, Brian?

Brian: My dad dressed like me: country-club casual. I got my style from him (and boarding school). I went to an all-boys grade school and had to wear a tie every day. That kinda stuck.

Tracy: The casual prep look is actually pretty solid in most situations. Anything that looks good on a yacht is a good goal to aspire to.

John: I know I’m a little extreme when it comes to this subject. I find it abhorrent when people don’t dress up to fly, for example, which seems incredibly archaic to most people. But flying sucks already, so why make it more unpleasant by dressing like you just rolled out of bed?

Brian: I’m with you 100 percent.

Tracy: Here’s a question: Why don’t men have to invest in and keep a rotating amount of lingerie? It’s the best illustration of the issue. Women are supposed to look good for men; men don’t have to look good for women.

John: That’s why I try to make at least a little effort every day.

Tracy: You do? On which days?

John: Rude.

Brian: True.

John: Ok, fedora guy. How are fashion expectations different for gay guys?

Tracy: Answer: They actually have expectations.

Brian: Gay guys are just more likely to notice when you miss, like brown shoes with a black suit.

John: Every guy should know that, though. But fashion magazines only recommend clothes that are ridiculously expensive. So most men just tune out their advice and end up wearing whatever the women in their lives give to them.

Brian: Safe bet.

Tracy: Again, it’s homophobia — knowing about girly things is as good as being gay. And straight men define themselves not by what they are, but what they aren’t. They aren’t gay, and they aren’t pussies, so they can’t traffic in the trivial concerns of those groups (i.e., fashion, vanity). This is why a man wearing a pink shirt is described as having “confidence.”

John: And there’s something about being part of a straight bro friend group that kind discourages adventurous clothing choices. Women should just dress down to men’s level. (Kidding, I’d hate that.)

Brian: That would look amazing.

Tracy: If women dressed at most men’s level, would anyone get laid? (Not to be reductive, but c’mon, what is the point otherwise?)

John: Who are we kidding? Men would still try to bone.

Brian: If men bought new clothes more often — like with a Trunk Club-style membership — would that help?

Tracy: Yes, if men would start with clothes that simply fit, women everywhere would probably fall to the ground weeping with gratitude.