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I have received a wedding invitation that specifies “cocktail attire” for the ceremony and reception. My investigation shows that this can mean any number of things. I come from Oregon, where formal attire means choosing one’s best flannel and scraping the mud off one’s boots. My wife has any number of stunning dresses that would fit the bill, but I don’t even own a suit. Is this time to buy one? Please give me some tips for navigating the rocky shoals of proper cocktail attire.

Thank you for your question!

The concept of cocktail attire originated in the U.S. during Prohibition—natural timing, given the irony intrinsic to the noble experiment: There was significant personnel overlap between the movement in favor of women getting to vote and the movement against anybody getting to drink, and the abstemious suffragettes supporting the 18th and 19th amendments inadvertently chased their daughters into speakeasies and such. They created the Drinking Woman—“an ideal rooted in newfound concepts of individuality and a denial of Edwardian matronly functions,” as the Costume Institute at the Metropolitan Museum of Art puts it:

She emerged at private cocktail soirées and lounges, and the cocktail dress, as a short evening sheath with matching hat, shoes, and gloves, was designated to accompany her. The cocktail affair generally took place between six and eight p.m. Cocktail garb, by virtue of its flexibility and functionality, became the 1920s uniform for the progressive fashionable elite.

At cocktail hour in 2014, a lady can always pass muster by wearing a little black dress. The gentlemanly equivalent of the LBD is a jacket, a necktie, and a nice pair of trousers. If you can’t be moved to buy a suit for this occasion, wear that, and wear it in the spirit of a sophisticated adult at ease, not of a teen tugging on his collar at Model U.N., or of an insurance executive soberly departing his retirement party.

Herewith, a cryptanalysis of other enigmatic dress codes that I, and people I know, have encountered on invitations.

“Lounge suit.” This baffles some Americans living in England, Rhodes scholars and dopey brokers alike. A lounge suit is just a suit: In the 1800s, English men of the upper classes wore strict, sober frock coats for work (if they worked) and lounge suits to play. The original lounge suit was called so because, soft and slack, it was worn to loll about the country or to relax at home. The lounge suit “was certainly not acceptable at the bank or the firm, nor at church, nor at highly formal social events in the daytime, nor for anything at all in the evening,” Anne Hollander wrote in Sex and Suits. In the 1900s, classes below the upper classes—people who hadn’t had the chance to lounge—started wearing them out and about, for business and pleasure, and here we are.

“Fancy dress.” This is a Britishism meaning “costume party.” Some British residents of New York City insist on using this phrase on invitations, despite its ambiguity on these shores. Some of those people do it strictly to remind us exactly how British they are, as if we’re supposed to be impressed. (I say to them, “This is America, pal. Learn the language.”) If you’re ever in doubt about whether a party advertised as a “fancy-dress party” is a costume party or a formal occasion, then show up wearing a tuxedo, but with a fanciful accessory on hand, such as a feathered mask or a backup bowtie.

“Highland dress.” This is a Scottish thing: You don’t have to wear a kilt, but if you own one, it’s time to get your tartan-flaunting on. Some Scotsmen wear nothing under their kilts. Some Scotsmen prefer boxer briefs. No true Scotsman argues against the logic of the jockstrap as an ideal underthing.

“Grown and sexy.” This is a black thing, and Urban Dictionary’s lexicographical game is in this instance tight, so here’s a lightly edited excerpt of its leading definition: Don’t even think of showing up at my function in baggy jeans, Air Jordans, platinum chains, and an XXXL white T-shirt. If you’re not in tailored Armani or Versace, stay your ass home! Also, unless it’s neo-soul, rare groove, or old school, you won’t hear it here. Want radio hip-hop? Go to that white kids’ club in the suburbs.

“Dress to impress.” The implicit emphasis on ostentation identifies the hosts as probable douchebags. Consider avoiding this party.

“Dress to Get Laid.” Since back in the day when Bret and Lethem and Ms. Donna Tartt and their peers were enrolled at Bennington College, students have celebrated an infamous pagan ritual of this name. When preparing to attend the debauch, you should cogitate on the fact that, on one level, every party in the recorded history of social life has been a Dress to Get Laid party, with the exception of some wakes and brises. Wear a T-shirt and jeans. Or a kilt and a jockstrap.

“Festive holiday attire.” You may be tempted to wear something corny. Try not to succumb to temptation. DON’T wear a Santa hat unless you arrive at the party in a sleigh. DON’T even think about a candy cane in your breast pocket or a poinsettia on your lapel; these accessories would be, in their hokum, only slightly less offensive than a mistletoe belt buckle. DON we now no apparel more gay than a red-and-green cummerbund.

“[Fill-in-the-blank] chic.” Miami event planners are known to possess, among other vices, a habit of declaring “tropical chic” dress codes. Native-born Herald reporters and Eurotrash art collectors alike know how to interpret this: linen pants, no socks. A son of San Antonio, describing a gala where the guys wore “Western chic,” recalls the footfalls of a stampede of Luccheses: “It was very J.R. Ewing—a lot of jean-and-jacket combinations, bandannas, turquoise, bolo ties, real tuxedos, and Texas tuxedos.” Last month the society page of the Times-Picayune told New Orleans ladies what to make of “summer chic” and “saucy chic,” saying of the latter, “I foresee a lot of low-cut shirts. … Possibly leather, too. And if that’s what the host is going for, so be it.” As you read this, invitations mandating “Yuletide chic” togs for would-be eggnog tipplers are sitting in mailboxes all across the country.

This columnist has mixed feelings about these developments. Of course, we always appreciate gentle reminders about trying climates and difficult terrain. (If a wedding is held on the sand at a beach resort, you want a heads-up, so that you know to wear boat shoes with your lightweight suit for the sake of gaining the traction you’ll need to evade hotel security at 3 a.m.) And, of course, we can’t quite disapprove of the bride and groom who—true story—explicitly discouraged seersucker on the invitation to their Cape Cod wedding. (They were fearful that their guests would fashion costumes from the fabric—a kind of drag show of preppy appropriation. They were trying to save guests from themselves.)

But the “____ chic” formula prompts wondering worries: Isn’t this rather controlling? Isn’t it somehow vain? Is the host trying to throw a party or supervise a photo shoot?

“Classy.” A colleague looks back on a New Year’s Eve party at a friend’s apartment: “The friend was an event planner who also does interior decorating, so when she wrote ‘classy,’ I think everyone kind of got the idea. She’s a Very Certain Type. (Loves wearing sequins on a Monday, weird vintage hats, etc.) For the most part the ladies wore little black dresses or nice vintage dresses with pumps. The dudes wore button-ups and jeans. Which, IDK? It didn’t seem like they tried that hard.”

“Business casual.” We all know the adage: To dress for success is to dress for the job you want, not the job you have. That is generally a good policy—but have you ever studied photos of media moguls pretending to relax at Herb Allen’s annual thing? Only a degenerate careerist would sacrifice his style to emulate the epic shlubbery of Sun Valley business casual. It’s awful—pro-shop ski vests over tropical shirts and Rupert Murdoch under a baseball cap and worse. The photos present evidence that some guys who wear business suits all the time simply have no idea what to do when unprotected by their constraints. Many of those zillionaires look unemployed, and unemployable.

“Smart casual.” The idea is to respect the spirit of business casual without looking stupid. Wear an OCBD, chinos, old-school canvas sneakers, and—it’s a shame to have to spell it out—a belt.

“Artsy casual.” You should wear a sack jacket, an untucked polo shirt, dark jeans, and freshly polished leather shoes, and if at all possible show up slightly stoned.

“Casual cocktail.” This is like a dog whistle telling women to wear flats, Tory Burch, probs. (h/t Shannon Elizabeth)

“Evening casual.” Hunh?

“California semi-casual.” No shirt no shoes no service, so bring along a shirt, but don’t fold it, bro: Roll it lengthwise to spare yourself some creases.