Pretty in Pink

How one man mastered shopping for his wife, and lived to tell the tale.
Pretty in Pink
SEP09 OMOI am rare among men. I actually clothes shop successfully for my wife, and I enjoy doing so. For most men, clothes shopping for themselves is a headache-inducing hassle, but doing so for their wife or girlfriend usually amounts to torture worthy of Amnesty International’s attention. I used to be such a guy. Not anymore. I’ve cracked the code, and in so doing, have not only earned my wife’s adoration, but the admiration of lots of women, particularly those who ring me out at pricey boutiques. I’m also the envy of many men who wish they, too, could figure out what to buy their sweetheart besides a Target gift card. But I haven’t always been like this; there was considerable trial and error along the path to feeling at home, or at least at ease, inside a woman’s boutique holding up a pair of panties to gauge if they’re the right size.

When I first conjured up the courage to buy clothes for my wife, Angie, I made the classic beginner’s mistake: Choosing items not based on what she may want or think she looks good in, but instead, what I thought she should want and would look good in. So I came home with some really booby, low-cut blouses, tight-fitting tube tops, and excessively snug sweaters, as well as anything that I could find at French Maids R Us. You get the idea. The effort was appreciated at first, but eventually it fell…well, flat.

Once I moved beyond my boob fixation, I began to buy less revealing—some would say “trampy”—clothes. I pretty much stuck with name brands, the big hard-to-screw-up ones, such as The Gap and Old Navy. This was an improvement for sure, but the mostly run-of-the-mill T-shirts, Capri pants, flip-flops, and hoodies I bought weren’t necessarily knocking Angie’s socks off.

Not to be defeated, I decided that I would do what I had heretofore avoided: Actually speak to someone in a woman’s clothing store. For guys, this is akin to stopping to ask for directions, only worse, because at least in that case we know what to ask (“How do I get from ‘here’ to ‘there’?”) even if we choose not to. When shopping for our main squeeze, however, guys don’t even know what to ask. To complicate matters further, we don’t have answers for the obvious questions posed to us. Here’s how my first discussion with a sales associate inside a women’s clothing boutique went down:

“So, what brings you in today?” the peppy twentysomething asked.

“My wife.”

“Oh, she’s here. Well, I’ll help her then.”

“No, she’s not here, I’m here. I mean, I’m shopping for her.”

“Wow, she’s lucky—and you’re brave.” That didn’t make me feel any more comfortable. “Well, what can I help you find?”

“I don’t know. Something nice.”

“Something nice, huh? OK, let’s see, we have lots of those.” She laughed. “Were you thinking something for work or something for fun?”

“Either one, as long as it’s nice.”

“A single piece or two, or an outfit?”

“Doesn’t really matter, whatever you think.”

“Well, what are some of her favorite colors to wear?”

I did a mental walk through Angie’s closet. “She wears all colors, though at the moment I can’t think of anything she wears that’s lime green.”

“OK, OK.” She laughed again. “What size is she?”

“Let’s see…”

She detected the blank look on my face. “Is she taller or smaller than me?”

“I’d say that she’s shorter and a little bit, uh,…”


“Yeah,” I said, feeling even more awkward, though thankful that she finished my thought.

“OK, she’s probably a two or maybe a four then. Let’s look around.”

IT WAS A rocky start, to be sure, but I hung in there as she pulled this blouse and that blouse from the rack, this pair of jeans and that one, this necklace and then that one. I pushed myself to envision my wife in each of the items. Some I couldn’t quite see, others I could. But I relied more on the salesperson’s recommendations than my own gut instinct. It paid off. When I got home and presented the clothes to Angie, I could tell by her reaction that “I” did a great job. She was happy, ecstatic even, but more than that she was shocked.

“Did you really pick this cute stuff out by yourself?” she asked.

“Damn straight,” I lied. Of course, I had help, but I reasoned that I was the one who ultimately said “yea” or “nay” to every item, so my lie was a little white one.

In any event, with that small victory behind me, I went shopping for Angie in another store a couple of weeks later, only this time I was better prepared. I had been paying closer attention to my wife’s wardrobe, not only what she wore, but what she didn’t. I had also made a mental note whenever someone complimented Angie on what she was wearing, as well as what pieces made heads turn, whether admiring women or lusty men. And yes, I learned Angie’s size—not just her dress size but her waist size, bra size, and even her shoe size, too. Armed with this intelligence, I was a much better shopper, though I still relied heavily on the sales associates for their opinions. I also leaned heavily, metaphorically speaking, on mannequins. I figured that if something looked great on a mannequin, it would look even better on Angie, who had the added advantage of possessing a head, hands, and feet.

My study and practice paid off. I was regularly bringing home clothes for Angie that looked fabulous on her, that she loved, and that other people noticed. When people would ask where she got a particular item, more often than not, she would smile, point to me, and say, “I don’t know, ask him; he bought it.” The person asking would do a double take, initially not believing that I, or any guy for that matter, was capable of such a fashion achievement.

Women are very impressed with this. Trust me. Whenever I bring shopping bags back to the office, they attract the attention of my female colleagues, most of whom ask to see what’s inside. When I pull out hip, fashionable clothes, they say things like, “I wish my boyfriend could do that,” or “It must be nice for your wife to have a personal shopper.”

For any single men reading this, I offer this advice: Go shopping for a woman—even an imaginary one—and then bring the bags back to the office. It may help you meet someone new. And if you’re not interested in anyone at the office, remember that women are often just as eager to set people up as they are to see what you brought back from the mall. My point isn’t that women are that shallow; it’s that men are that bad at shopping. Even an iota of ability in this area makes you look like a superhero, dude. So, gentlemen, step back from the computer keyboard and and get your lonely self—and your wallet—to the shops at Kenwood Towne Centre or the boutiques in Hyde Park, O’Bryonville, or Northside. I predict you’ll be holding hands with a woman in no time. She may be a psychopath, but at least she’ll be well-dressed.

WHICH BRINGS ME to an important point: Some women will be insanely jealous of what you do for your wife. Some won’t believe that you’re the one actually doing the shopping. Nothing you say will convince them that you haven’t hired a personal shopper or bribed your sister or mother into doing the hard work for you. Also, some guys will be wildly envious that you can do what they can’t seem to even conjure the courage to try. And some men will want to dismiss your talent with that childish, idiotic taunt that is a favorite of guys without any self-confidence or true security in their own sexuality: They will call you queer. Once, at a work-related conference, when Angie explained that I bought many of her clothes, a guy in the group remarked, “He must be gay.” In our culture, clothes shopping is a stereotypically feminine act. I get that. Just as I get that some guys—straight and not-straight—love shopping as much as any woman. Despite what my rational brain recognizes, though, I’ll admit that I sometimes don’t practice what I preach. Instead, I allow myself to fall quiet about my shopping prowess around other men or avoid eye contact with those guys who just sit in the corner, stewing, waiting on their wives or girlfriends, while I shop on.

A few months ago I was standing at the corner of 14th and Vine, pausing in the middle of another shopping spree, this time at Park + Vine, MiCA 12/v, and Metronation in the Gateway Quarter of Over-the-Rhine. In each hand I held two logo-emblazoned shopping bags with color-coordinated tissue paper poking out of the top. Yes, I felt rather girly, particularly since a gargantuan dump truck had come to a stop at the intersection. The light signaled “Walk,” and so I did, right in front of the truck, the driver sitting up high, as if on a throne, while some of the several tons of busted concrete and rebar he was transporting to the dump rose even higher than his dusty cab. We made eye contact for a nanosecond and then each glanced away, two animals passing in the jungle, choosing to avoid one another. I wonder what he thought of me and my frilly bags. Did I remind him of the pencil-necks he used to bully in high school? Or did I remind him that he still doesn’t know how to shop for his wife? I didn’t bother asking.

But onward I shop, undeterred. In fact, in some of the places I frequent, the sales associates know me and pretty much leave me alone. It appears I no longer need any help. At least when it comes to women’s clothes. 

Illustration by Kevin Miyazaki
Originally published in the September 2009 issue.

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