You don't expect the guys on Reddit to be well-dressed.

More likely, you know them for spreading memes or raising money for much-maligned bus monitors. They have strong opinions about Linux, the open-source operating system. They love science. If you're not a nerd or don't spend much time on the obscure corners of the Internet, you might not know them at all. But behind the news-aggregator's aggressively geeky front page, there hides a surprisingly lively men's-wear community — in some ways, the sharpest one on the web. It's not Style Forum, that trad oasis where guys discuss the finer points of woven ties, or even Superfuture, where the streetwear kids cut their teeth. It's just a page called "Male Fashion Advice." You'll know you're in the right place because you'll see Reddit's signature alien peeking out of a chukka boot. Clever. Or, as one Redditor put it, "nowhere else on the planet can you find fashion broken down so clearly for noobs." (In web speak, he means novices.)

The forum's defining feature is a never-ending avalanche of posts called "What I'm Wearing" — a stream of self-portraits usually taken with a shaky camera, hardly any lighting, and even less self-assurance. Take a user that goes by coprhgen, for instance, who once offered up a photograph of himself dressed in a downy white tee and Nantucket Reds. He wasn't sure he could pull off the pants, but three Redditors quickly corrected him. "They'll only look good if you wear them confidently," one chimed in, with quite possibly the oldest advice in the book. But with a whole forum cheering him on, how could he not?

Anywhere else on the web, a thread like this would devolve into some sort of swagger-off almost instantly. In the peacock courts of Tumblr, say, it's not unusual for a gentleman to arrive kitted out in $10,000 worth of hand-loomed tweed, only to make back his money in the Internet version of a hundred thumbs-up. Because why show off for your mirror when you can show off your friends? On Reddit, it's not even clear that the men have dressed up. The outfits are polo shirts with jeans, or a slimmed-down version of business-casual, with sport shirts tucked reluctantly into belted khakis. These are some of the safest players in men's style, but you wouldn't know it from all the questions they have. Should I be tucking in this shirt? Is this better with pants or shorts? Boil it down further, and you'll find an even simpler question: Do I have permission to look good? Does what I'm doing even make sense? The answer, of course, is yes. And in a place where no one is trying to set himself up as an expert, most responses are that direct. That outfit works. The other, not so much. I think it's the shoes? You're probably buying the wrong size shirt.

Since it launched in 2010 2009, the Male Fashion Advice page has become the sole place for uber-novices to ask questions — and get almost instant responses — on sartorial topics that are so simple, most other online resources don't bother addressing them. One poor gentleman started a thread with a tight henley and a simple question: Am I too skinny to pull this off? Some 350 comments later, no one has said much about how to dress a slight frame. They're too busy making Dexter jokes and talking about how large his head is. (To be fair, the collar makes it look pretty big.) They're ribbing him, the way you might tease your younger brother before a first date. It's about creating confidence. Going for it. And being ready to take some shit in the process. Which is to say, the permission to dress well only goes so far. They care enough to look good, but no more than that — and even the slightest hint of pretension is enough to send them scuttling back to the old postures, the camraderie of the ever-critical commentariat.

"I like giving advice, and I love to nitpick," says Hooplah, a 22-year-old Redditor who works as a paralegal when she's not online. "I don't think most people on Reddit know I'm a girl." That anonymity is part of the appeal. It's also further evidence that these young guys are looking for any help they can get, no matter the bona fides of Reddit's "expert sources," all who become trusted advisors in the same way your bank telephone service might: by always being available. Now that she's commented enough to have a reputation on the site, Hooplah says she gets private messages every week, sometimes more than once day, asking for recommendations or advice on a particular rig. One back-and-forth became so elaborate, she ended up sending a three-page Word document of starter items he'd need for a complete wardrobe — all without taking credit, telling another soul, or even sending me her list.

One thing that wasn't on it: suits. Tailoring, in general, is viewed with suspicion. Even Hooplah is quick to point out that she's not one of those girls who think all guys look better in a jacket and tie. The men on Reddit are comfortable with shorts, and well-disposed towards t-shirts, so long as they fit and don't have anything ironic printed on them. Uniqlo is big here, along with fancy Nike hi-tops and a good oxford-cloth button-down from J.Crew. But leave those more formal pieces to guys who, uh, already know what they're doing.

The one exception to this casual, affordable, Internet-ready mandate is a good pair of shoes. Even under a pair of jeans, it's not unusual to see something from Alden or Allen Edmonds. Styles like double-monk-strap shoes are too much muchness for Reddit, but the board is fully sold on the power of an American-made wingtip. So much so that they even waged a mini-campaign against Nordstrom in July, after the department store sold one Redditor a scratched-up pair of AE Strands. It provoked so much web-rage that the Allen Edmonds CEO and President, Paul Grangaard, ended up wading into the forum to assure them that, no, he wasn't selling them faulty shoes. "Although we strive for perfection," he wrote, "our human processes don't always get there." When asked about it for this story, Grangaard came off both eager and justifiably nervous. "People don't pull punches there," he says. "But you never know whose influence may be the tipping point." These kids, still in their infancy of style prowess, have some power; any growing brand wants to remain on their good side, and not just because e-commerce executives are worried about hackers seeking revenge.

But despite their increasing sway, you still won't find much swagger. There are none of those "influencers" that clothing labels are hunting down to represent their brand on Pinterest or Tumblr. It defies every inclination of the Internet, but the people on this board still don't seem terribly full of themselves. Most of the users will tell you they discovered the board after a struggle with depression or a hard-won weight loss, rather than a new job or an inherited wardrobe. In general, most only spoke anonymously for this article, lest they came across as a guys who actually cared. Which is strange, considering that some of them post as many as 18 times an hour, spending whole weekends on the boards. That's a lot of time, especially when you consider all the other ways that 14-to-22-year-olds could be spending their summer days or after-work hours. To them, dressing well is a hobby, not yet a reality. So, recently, when a gentleman strolled into the forum to show off his new pair of Imogene + Willie floral shorts, the response was a mix of awe and confusion. One guy asked, How do you afford $140 shorts? The answer came back: Hard work and saving. And, then, a few minutes later, the most American of asterisked corrections: *Credit card.

Well, at least they've got that part figured out.

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