Gentleman Scholar

What Kind of Lingerie Does a Gentleman Buy for Valentine’s Day?

Overthinking underthings.

Please send your questions for publication to (Questions may be edited, or invented.)

Troy Patterson.
Troy Patterson.

Photo by Christina Paige

What kind of lingerie should I buy my new girlfriend for Valentine’s Day? She’s a 34-year-old Ph.D., 36D, and enjoys overthinking underthings. Please advise.

The contemporary gentleman celebrates his sweetheart at the Feast of Saint Valentine partly because of Chaucer’s Parliament of Fowls, partly because of the early-19th-century reform of the Royal Mail, partly because he’d be in the doghouse if he failed to. Just do it. Construct a heart and send a card. Sear a steak and make a sauce. Buy a gift, some kind of gift: a box of chocolate, a strand of pearls, an eau de parfum that fell off the back of a camion de livraison—all are worthy options.

No Valentine’s Day gift is quite so ripe with potential (or quite so fraught with peril) as lingerie. Therefore, herewith, we give you a gentleman’s guide to ladies’ intimates. Our aim is to edify fellows of good taste—even, and especially, those fellows inclined to strategically misplace their good taste in light of this special occasion. We regret that we have no particular guidance to offer those fellows whose bedmates are fellow fellows, but here’s a link to the Hanes sizing chart.

Modern lingerie began in 1947. This was, of course, the year of Christian Dior’s iconic cinched silhouette—the New Look that brought a renaissance of crinoline and corsetry. But also it was the year that one Fred Mellinger moved his fledgling business from New York to California and inaugurated Frederick’s of Hollywood, soon thereafter gaining the patronage of “movie stars, ordinary women who would be femmes fatales, and, in much smaller but significant numbers, hookers and transvestites.” His innovations included the padded bra, the push-up bra, the padded girdle, and the introduction of the  “scanty panty”—that item known, less goofily, as the thong—to the mass marketplace.

It must be said that Frederick was of Hollywood. From the days of Clara Bow, movieland led the way in glamorizing and normalizing fancy underpants, and Frederick’s mission to uplift womankind was informed by his experiences peering at Betty Grable and other pinups while serving in the Army Signal Corps. The foundational fantasy of his garments—and, thus, the American idea of lingerie at large—is cinematic.

What does this mean to you, 21st-century dude? As regards the actual experience of shopping at Frederick’s of Hollywood, not much. Perusal of the website suggests rampant tawdriness—and not the fun kind, either. The safe bet, if you were feeling high class, would be a pair of French silk stockings ($80), but if you were feeling high class, why on earth would you be looking at that website? You’d be much better off going Old Hollywood: Search eBay or Etsy for a classic Marabou-trim baby-doll nightie. If you give the thing a good steam cleaning and call it vintage nightwear, as opposed to used pajamas, it won’t even be weird. For a kitschy kicker, gift wrap it with a pair of Glamour Girl Marabou Slippers ($29).

Like a strange combination of Norma Desmond and Claude Rains, Frederick’s faded, and now is the No. 2 lingerie retailer in the U.S. Of course, it’s not No. 2 in the sense that Pepsi or Hertz is No. 2. The Washington Generals provide a better point of comparison. The market leader is, of course, Victoria’s Secret, which I couldn’t bear visiting alone, fearful that the pout of model Adriana Lima, infinitely reproduced on in-stores displays, would somehow glossily bludgeon me into a regrettable purchase.  

Better to gird myself with a tour guide. I arranged a visit with Bobbie Smith, a lingerie expert who operates under the nom de brassiere Ms. Fit. In her office, she laid out a theory that “lingerie can be relationship therapy,” proceeding to share the tale of her best friend, whose investments in lovely little lacy things did not accrue much interest from her better half. This was a source of some distress, until they talked it over and it emerged that he’s “just into white cotton panties.” (GapBody sells them for $10.95.) Further, Smith brought to light a frequent complaint among women who have just purchased themselves “cute, attractive, sexy pieces”: “He just wants to rip it off. He’s not enjoying it and appreciating it.” She encourages indulging complacencies of the peignoir rather than rushing into unsubdued elations: “Enjoy it for more than five minutes, whether that’s playing Jenga or the boyfriend stripping down to his skivvies and the two of them cooking together.” A Calphalon 13-inch Splatter Screen ($19.95) would be highly desirable here.

Where were we? On our way to Victoria’s Secret in SoHo, but not for long. Smith had a quick kind word for the VS approach (”it’s cheap and cheerful”), but she got the biggest kick out of sharing her hilarity at the Bombshell Bra, which adds two cup sizes, at the cost of some dignity. “This,” she said, squeezing its sponginess, “would actually be a really good fit for a man.”

She was rather more admiring of the wares at a little boutique a few blocks away, where a window display featured a Kriss Soonik lace bodysuit ($220) exemplifying a going trend—underwear as outerwear. (The online ad copy suggests that one may “seduce the world” by wearing the thing “with a black skirt and killer heels.”) Smith observed that it would be plausible to wear the bodysuit backward, so that its peek-a-boo back becomes a peek-a-boo front: “You can open it here so you don’t have to rip everything off.”

For an encore, I arranged a second field trip, this time heading out with Katrina Eugenia, an artist and model who writes a column called “The Power of Lace” for an industry website called the Lingerie Journal. Eugenia hails from the school of thought that a gent buying lingerie for a lady should shy away from bras in favor of teddies and nightgowns and robes— “just stay away from anything too lewd, unless you know she’s into it”—because the issues of proper bra fit are too difficult. Rather, the proper way to buy your regular date a bra is to take her on an irregular date. “The first gift my boyfriend ever got me was a bra,” she said. They were walking past a store, and she mentioned a cute unmentionable in a window: “He said, ‘Well, why don’t you go in and try it on?’ It was a win for everyone.”

Our destination was the reliably chic, compellingly ridiculous Agent Provocateur. The shelves were understocked that day as sales associates moved out the last of the winter merchandise to make way for a spring collection advertised by a campaign in the key of Stepford Housewifery. Pickings were slim, though the jazzy sass of the Inga halterneck playsuit ($3,900) was undeniable.

Now, at this point, I would normally start fretting about whether I’d answered my correspondent’s question sufficiently, but as he is a rhetorical device of my own invention, I think he’ll be OK. That said, I will point out that there is a fairly nifty body of academic work done on this scanty subject and suggest that the letter writer give his girlfriend a copy of Jill Fields’ An Intimate Affair: Women, Lingerie, and Sexuality, which takes a frisky approach to the underwiring of gendered identities. “Intimate apparel,” she writes, “places the body in ambiguity. Adorned in undergarments, the body is clothed but not dressed.” Read it in bed?