Jack Asks Jill About Women's Clothing

Jack Asks: At what age do women decide to stop shopping in the "Juniors" section and start shopping in the Women's section? And why are so many of the clothes in the Women's section unflattering, dull, and sometimes downright hideous?

Jill Answers: This is a hard question. Are we supposed to ask each other hard questions? I thought this was just for fun? I have a headache.

Okay, okay, let's get on with it. I've actually often wondered this same thing. I mean, upon someday birthing a child, will I suddenly acquire a fondness for heavily patterned holiday sweaters and pleated pants? Will menopause bring with it a penchant for muu-muus and bad haircuts? Do older men suddenly become attracted to this type of attire and that's why women wear it? Will I have to wear gigantic white cotton underwear too?

Okay, I know that last one has you hyperventilating since you almost lost it when I said I might purchase some Spanx. Calm down for a minute.

Anyway, here's what I've come up with as an answer to your question -- I used to try get my mom (who is pretty young for a mother of a 32 year old) to wear hip, cute clothes. She'd put them on and I'd ooh and aah over how awesome she looked. Then she'd scrunch up her face in the mirror, tug on the "tight" shirt, and say she felt fat or that she looked like she was "trying too hard to look young". You see, there are a couple of things to know about my mom: 1) she used to be a size 4; 2) she used to be quite the snazzy dresser in her day. She's not a large woman now, but she's certainly no size 4, 32 years and 4 kids later, you know? I think in her mind she feels like she can't dress trendy anymore because she doesn't look how she used to look. This, to me, seems absurd. Is she a tiny 20 year old size 4? No, but that doesn't mean she can't look cute & trendy. I mean, I'm not encouraging her to wear mini skirts and tube tops here, just to wear shirts that, oh, I don't know, FIT. Instead, a lot of the time she masks her no longer size 4 body in XXL sweat shirts. Ridiculous, I say!

So...what's my point? I am guessing that sometimes women feel like if they don't look like they did when they were 20, they should dress "more appropriately". The problem here is that their idea of "more appropriately" isn't really....appropriate. Flaunt what yer mama gave you, right? Just because you're 50+ years old and gravity has taken a toll doesn't mean that you can't be a hot mama! Right?

That's what I'm going with, because I plan to squeeze my ass into corset tops and stripper heels even when I'm 50. That seems like a good idea, right? Maybe that's not exactly what you meant....

Jack Follows-Up: For the record, older men DO NOT suddenly become attracted to heavily patterned holiday sweaters, pleated pants, or gigantic white underwear that could also be worn as bike shorts. Also, the idea that older women "don't want to dress too young" confuses me. Who said anything about trying to look young? Just try to look attractive, OK? And by "try to look attractive," I mean try to never, ever, ever wear mom jeans.