I suppose an end-of-2017 review should come at the end of 2017, but it’s better late than never. Much has already been written about fashion’s obsession with obnoxiously ugly clothing as of late. Moreso than ever, the last year of fashion has been about playing up notions of bad taste. Velour track pants with a stripes running down the outseams; Gucci jackets that look like a teenager’s Lisa Frank notebook; oversized suits previously favored by ‘90s R&B singers; fanny packs that look like they come with a package of Werther’s hard candies; and defiantly ugly sneakers that make even Sketchers look good.

To be sure, this isn’t the first time fashion has been obsessed with ugliness. “Traditional” forms of beauty haven’t been popular in over fifty years, since couturiers and tailors dressed elites in custom gowns and suits. And just as recently as five years ago, menswear was obsessed with gauche and tacky clothing labeled as preppy or Italian. The difference is the source of inspiration. Whereas menswear used to be about aristocratic takes on vulgarity, 2017 was more low-brow. The only thing that separates FU critter pants from velour sweats is economic class.

The question is obviously why – why would anyone want to wear ugly clothes? Why would anyone want to look “low class?” Fashion is ostensibly about making yourself look better than your actual station. Why, then, would anyone choose to look tacky, cheap, and ugly, while also paying thousands for the privilege? Unlike the early aughts, tackiness today isn’t about being ironic. There’s no tongue-in-cheek reference to authenticity or a wink-wink about how the wearer actually hates the item. Some things are so ugly, they’re simply now thought to be good.

Part of this has been the ‘90s revival; the other part is just about fashion – people wear things simply because they’re trendy. The other more important part, particularly as it pertains to menswear, is about a shift in attitudes. Even among men who used to wear Alden brogues and classic Barbours, ugly clothes have become popular for a simple reason: they’re tremendously fun to wear if you have a sense of humor about yourself. And there’s really nothing more to it. The emphasis is less on looking good and more on having a good time.

This shift in attitudes can’t be overstated. Ten years ago, men’s fashion was obsessed with “the right way” of doing things. People would ask, is this trad? Is this classic? Is this well made? Is this Goodyear welted? Is this real cashmere? Is this handsewn? Is this fully canvassed? Is this something I can use for the rest of my life? Am I wearing clothes correctly? Does this look sufficiently and naturally nonchalant?

Altogether, it’s an incredible amount of fretting for guys who rarely even leave their offices. The Onion had a great headline last month: Patagonia Introduces New High-Performance Jacket Specially Designed To Protect Wearer On Walk Between Front Door And Car. “With two layers of insulating synthetic down, this jacket will shield you from whatever Mother Nature throws your way during quick trips to the mailbox or while running the trash to the curb,” they wrote.

This sort of rule-based approach to style – the idea that shopping for clothes is like shopping for electronics, and there are certain truths that govern aesthetics like physics – sucks all the joy out of clothing. And it causes an undue amount of anxiety for what’s an inherently trivial subject. It almost felt like people wanted investigative journalists to uncover the secret rules to being stylish, with Consumer Report ratings on whether a brand is worth buying. In that sense, even if I don’t care for Demna Gvasalia’s version of Balenciaga, I think it’s great that fashion has become less serious and more emotive. Fashion, at its best, is about having fun. Clothes should empower and make you feel good. I scratch my head at people who wake up in the morning every day and decide to post angry messages online about something as stupid as pants.

Emotive fashion can be great even for guys who have a more classic sense of style. In fact, I’d argue that most stylish men dress from the heart. This is, after all, what used to be called having a sense of taste. In his often-cited essay on aesthetics, "Of the Standard of Taste,” David Hume claimed some people are in a better position to understand beauty based on their experiences.

As an empiricist, Hume sought to reconcile the difference between subjective and objective judgments. Subjective judgments (what Hume called sentiments) are always right because they never reference anything beyond themselves. Objective judgments (what Hume called determinations), however, reference an outside quality, so they can be verified or falsified. Beauty is not an inherent quality in something, so judgments on beauty are sentiments, not determinations, for they only exist in the mind. At the same time, Hume wanted to recognize that some judgments are objectively better than others. In Hume’s essay, he famously claimed that no one with a right mind would think there’s an equal level of genius between the works of John Ogilby and John Milton, or John Bunyan and Joseph Addison. Granted, our judgments are affected by time and cultural conventions, and thus subject to change, but our senses are sharpened through experiences. A true judge, Hume wrote, has a “strong sense, united to delicate sentiment, improved by practice, perfected by comparison, and cleared of all prejudice.”

Think of it like this: you can explain all the rules to someone who just became interested in tailoring, but an eye sharpened by experience will notice nuances in the fit, silhouette, and style that a novice will likely miss. And thus, that eye is a better judge of what looks “good.” Often, those judgments about beauty are emotional – they excite the heart and mind – and can’t be taught through scripts and rules alone. I imagine that’s partly why some guys always look great, despite breaking the rules, while others look like hell despite being following them slavishly.

Last year, I interviewed Brain Davis of Wooden Sleepers for a post at Put This On. Towards the end of our conversation, he said: “We’ve spent so much time talking about effortless style, but sometimes guys get too worked up over details. Just put on the jacket and wear it. A lot of this is much simpler than sometimes it’s presented online. It goes back to the first day of school and wearing a jacket that makes you excited, a jacket that makes you feel cool. It can be about a feeling.” I couldn’t agree more.

To that end, here are some photos I think are tremendously stylish. They don’t teach you any rules, and many of the clothes will look stupid on other people, but they give you an oh-so-great feeling, which I think can help guide you to better clothing choices. May 2018 be about dressing from emotion and having a good time.