03/18/2010 05:12 am ET | Updated May 25, 2011

One Man's Adventure in a Women's Clothing Store

I've worn a Boston Red Sox cap to Yankee Stadium. I've campaigned for Republican candidates in Philadelphia. And I've entered Israel with a Syrian stamp on my passport. But nothing could have prepared me for the scrutiny I faced when I walked into an Ann Taylor Loft to buy holiday gifts for my wife and mother.

Immediately, skeptical eyes confronted me. "Sir, can I help you? Do you know what you're looking for?"

Naturally, the first question made me feel welcome. But the condescension of the second question made me wonder whether - despite being a spry 26 year-old - I looked like a confused 90-something.

"Er, I'm looking for holiday gifts for my wife and mother."

"What color hair do they have?"

This rattled me a bit. Was I supposed to consider my wife and mother's respective hair colors when picking out sweaters for them? And, by having never done so in the past, had I been failing at gift-giving for my entire life?

"My wife is a blonde and my mom's a brunette," I said. "What do you recommend?"

I was starting to despair. But the attendant reassured me. "Hold on a minute. I'll check in the back." As she walked away, I started combing through a nearby blouse rack.

"Hi. Can I help you?" It was a different saleswoman. "Are you finding everything you're looking for?"

What was I looking for? Oh, right, gifts. But was I wasting my time looking at ruffled tops for two women of opposite hair colors? What about pinstripes? Can blond-haired women wear pinstripes? I was totally lost. And The Back had apparently swallowed the previous attendant.

"I'm looking for gifts for my mother and wife," I said.

"What do they look like?"

"My mother is a brunette, and my wife is a blonde."

"No, I mean what size are they?"

Finally - a question with implications that I understood completely! "They're both extra-small," I said self-assuredly. "I'm okay. I'm just going to look around."

And so I did.

"Are you okay, sir? Can I help you find anything?" It was yet another saleswoman.

"How do you think these work for my mother? She's in her fifties," I said, holding up a violet cardigan alongside a white, long-sleeved blouse.

"Well, what kind of figure does she have?"

"Um, she's thin."

"No, I mean is she big-chested?"

My heart stopped. Was I really being asked to comment on my mother's ... ?

"Why does it matter?" I asked, praying for an escape.

"Because this shirt might show cleavage, and women in their fifties occasionally feel uncomfortable with that."

After initially grossing me out, this saleswoman was actually giving me some useful information. So she showed me some other blouse options and, after a thorough tour of the store, left me to my own devices. Twenty minutes later, I'd picked out two different cardigan-and-blouse sets for my wife and mother.

"Sir, are you finding everything all right?"

This was getting annoying. I was finding everything just fine. Didn't she see the nice cardigan-and-blouse sets that I was holding in my hand? Or was she asking me whether I was "all right" because these sets were poorly chosen? I solicited her input just in case.

"What do you think of this set for my wife?" I asked, holding up a white cable-knit sweater cardigan alongside a black blouse meant to go under it.

"Hmm ... those are good colors." Then came the uppercut. "But the blouse is a bit too fancy for the sweater, because cotton sweaters are meant to be more casual."

I was really in over my head. I can evaluate color combinations - but material combinations? Forget about it.

"Why don't we try this other sweater?" she recommended, aligning the blouse with a plum-colored, waist-tied, woolen-alpaca-acrylic cardigan sweater. It looked decent, but I was still pretty convinced that the white sweater - cotton or not - had looked just as good. So I called over yet another salesperson.

"How does this combo look? Or does the white one look better with this blouse?"

"Oh, the purple looks amazing!"

Who was I going to trust to pick out women's clothing - my own eyes, or actual women? So after a good half-hour of striving to assemble two decent sweater-and-blouse sets, I finally submitted to the logic of being a man in Ann Taylor Loft: I left the ultimate decision in the hands of well-experienced professionals who had worn women's garments for their entire lives.

At the checkout counter, the store's lone male employee took me aside. "Sorry if you were hassled a lot," he said. "We just don't get that many guys in here." This made me wonder: did I really need all the help I'd been given, or had the saleswomen imposed the soft bigotry of lower expectations on me because of my gender?

And then a higher-than-expected tab hit me. I wasn't the victim of sexism - I was just easy prey for solid salesmanship. Or saleswomanship.

"You can get 20% off with an Ann Taylor Loft Rewards Card," he said.

I'll never leave home without it.