There comes a point in every hetero relationship when a man considers treating his lady to some expensive undergarments. It might be your way of celebrating her physical form while making it clear just how much you lust after her. It could just be a random surprise gift to show your affection on one of your relationship’s more drowsy days. And while giving a woman lingerie can also seem like a somewhat selfish present that’s more for your own fantasy than her comfort, it’s okay so long as your messaging is clear. It’s all in the presentation.

Whatever your motivation, buying lingerie can be a harrowing experience, especially for any self-respecting male whose idea of fashion and clothes shopping is to bulk order plain black, navy and grey t-shirts online from Uniqlo. Looking for lingerie, by comparison, can be confusing, frustrating, and overwhelming to the point where you want to give up and instead plan an evening of binge watching episodes of Law & Order: SVU with your significant other. But don’t fear—here’s your cheat sheet into a world of teddy sets and lace-trimmed panties.

Sizing Is Crucial

The most important rule of all when shopping for lingerie is to buy the right fucking size. Get this wrong and your attempts to perk up the old bedroom routine will have the opposite effect. If you buy a size too small, she’s going to think that you think she’s smaller or slimmer than she actually is, which opens the door to body image and confidence issues—none of which do much to put either of you in an amorous mood. Also, there’s little sexy about anyone busting a gut to squeeze into something that clearly does not fit.

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Likewise, veer towards the other end of the spectrum and buy a size too large, and she’s going to think that you think she’s larger than she is, which is rarely seen as any sort of compliment for anyone outside of the world of professional eating. You pretty much cannot win when it comes to buying alluring underwear if you don’t nail the size.

To that end, you’ll need to do your homework before hitting the store. Ideally, you’ll want to get a couple of sneak peek of the labels in her underwear and remember not just the size she seems to wear but also her most worn brand (being that sizes can differ wildly between brands). Being gentlemanly and offering to do (or drop off) the laundry is one way you could stumble across such vital information. You might also be able to take a mental note next time you’re in mutual undressing mode. (Decorum note: Obviously don’t go rummaging through her drawers when she’s out of the room if you’re in the early stages of your courtship, and unless you know she’d be okay with it.)

Big recognizable brands are your confidantes here, and ideally you’ll come away knowing that you’re gonna be shopping for a size medium in Victoria’s Secret camisoles or that she wears a large in Anthropologie shabby chic pastoral panties. Note this information down on your smartphone if you’re prone to bouts of forgetfulness.

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Also, this research stage is a good time to get a ballpark feel for what her general tastes and preferences might be—you probably want to avoid presenting her with a thong unless she’s shown an enthusiasm for wearing one before.

A Lacy Minefield

Once you’re armed with her size and have an idea about a target store to hit up, you’re gonna need to deal with the exciting world of lingerie buzz words.

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First up, skip over the bra and panty sets. Bra sizes are the algebra of the clothing game and you’re probably gonna get the math wrong even if you’ve faithfully recorded her cup size and whatnot.

Slips and babydolls (which may or may not be the same thing) are a good place to start. These are those one piece things that kinda look like shorter summer dresses. The fact that they usually have adjustable straps and are meant to flare out at the bottom means you have a greater safety net when it comes to sizing mishaps. You could also pick up some matching panties to go with the slip, which would help it seem like you put a lot of thought into this.

If you’re feeling more confident, dabble with a teddy or bodysuit. These are fitted—so think like a one-piece swimsuit—and can create a more contoured look. They are also often available in playful themes like, say, a sexy-cat costume teddy, should you swing that way.

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A sleek lace or silk gown—as opposed to the beloved but worn-in robe she schleps around in at the weekend—can also be a great piece to begin with, especially if you’re feeling really unsure about the whole sizing and style game.

Colors Matter

Red, white and the always flattering black are the classic base colors and dominate most lingerie ranges. You could attempt to match the trilogy to your lady’s skin tone, hair or eye color, but the chances are she’s already done the work for you—so take a cue from her existing wardrobe, perhaps paying attention to the outfits and dresses she dolls herself up in for a fancy dinner date or a night out with the girls.

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Pro tip: She’ll figure it out if you’re buying her lingerie in the color of your favorite sports team.

Who’s Pleasing Who?

Once you’ve narrowed down what type of lingerie you’re in the market for, you’ll need to address a broader philosophical point: Who are you really buying it for?

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If you totally get off on the idea of seeing her in, say, some see-through red lace, that’s cool, just make sure you present it to her that way. Maybe write a short note or whisper in her ear that you really want her to wear this for you. That way she’ll know it’s a one-off thrill-seeking thing and that you don’t really see her as a vampy continental trollop. The key here is to deliver your request in a way that makes it obvious that it will be mutually beneficial in the end. What do you want to do to her as she wears it? Say that.

Similarly, you might be trying to play up to a fantasy or desired look that she’s told you about mid-way through that second bottle of wine the other night. In that case, make sure you shop for the lingerie that will make her excited to wear it, even if it might not be to your own taste. The game of sex can take a selfish turn at times, which is cool as long as you’re open and on the same page about it. So try and avoid a mood-killing middle ground where she’s dressing up in an ensemble that she thinks you want to see her in, but you’re both secretly humdrum about the whole shebang.

Avoid Sales People

Sure, the experience of entering a lingerie store can be overwhelming. Not because anyone is judging you like you’re a weirdo or a pervert—although, let’s be honest, at some point you’re going to assume someone’s thinking that of you—but because of the sheer amount of skimpy clothing on offer. It can take a minute to get your bearings and track down the items you’re after. This apprehensiveness is something that commission-crazed sales assistants seem willing to exploit, mostly because they’ve got a commission on the line.

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To that end, as soon as you’re approached—which will likely be before the entirety of your body has even fully entered the store—I’d recommend smiling at the assistant and telling her in a cheery but resolute manner that you have an idea of what you want and will find them should you have questions. It’s not like the sales assistant actually knows the person you’re buying for, or has any idea about her tastes, size, favorite colors, or willingness to sport a sexual cat costume teddy. When nagged, be strong but polite. You’re buying a very personal and intimate gift, so it follows that you’re going to be the best judge of it.

On that note, ask questions about materials or cuts once you’ve narrowed your options down. And if you don’t find the perfect get-up after a while, don’t be afraid to leave the store empty handed and just go and buy her some fancy socks. There’s not really any sort of compromise in the world of lingerie—it either hits the spot or it leaves you both somewhat sexually flatlined. Also, socks are a really great gift. Seriously, they might have a reputation as a cliched Christmas present from the uninspired, but everyone loves new socks.

The Presentation

Most stores will offer to gift wrap lingerie for you—and you should definitely take them up on the offer. This isn’t a gift that needs an extra frills or bespoke wrapping paper, so store branded wrapping will work fine. Adding a card or a note can be cool, but the idea here is to conjure up feelings of spontaneity and excitement. She should feel wanted and coveted—you know, that you’re consumed by an insatiable, burning desire for her—so confidently slipping her a bag of lingerie and whispering something risqué in her ear can be a charm enough.

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Or, you know, leave the lingerie on the bed like in the movies. Though, if you have a pet this might just arouse their curiosity and you should keep them out of the room.

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A final note: Always remember to take the price tag off the lingerie, even if you assume the sales assistant has done so when they asked if you’d prefer a gift receipt. Money might not be able to buy you love, and you definitely don’t want to put a price on sex.


Phillip Mlynar lives in Queens, NYC. When not writing about rappers for Red Bull, NYLON, and the Village Voice, he muses on the feline form for Catster. His Twitterclaims he’s the world’s foremost expert on rappers’ cats.

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Illustration by Tara Jacoby.

Adequate Man is Deadspin’s new self-improvement blog, dedicated to making you just good enough at everything. Suggestions for future topics are welcome below.