I was on the subway a few weeks ago, coming home from work, and I noticed a woman sitting nearby wearing this very cute and flattering black dress. She was one of these effortlessly stylish people, with cool glasses and a great haircut and very expensive shoes, and she had a pretty rockin' body, to boot. As we got off the train, she was a few steps ahead of me. From her lengthy strides and deliberate gaze, you could tell she knew how effortlessly stylish she was and how rockin' her body looked in that dress.
She was still in front of me as we emerged onto the sidewalk, and after a moment or two, I realized that you could see RIGHT through that cute and flattering black dress. It was some kind of knit fabric; maybe it was a few years old or perhaps a size too small, but in any event it was pulled taut and you could see everything from stem to stern, including her black thong undies.
There she was, strutting along the streets of New York, undoubtedly having gone through her entire day -- picking up a latte and croissant in the morning, riding an escalator in her office building, sauntering past countless cubicles and coworkers to and from the bathroom, heading out to lunch, attending an afternoon meeting, popping into a boutique before getting on the subway -- without realizing that her rear was on view for all the world.
I thought about tapping her on the shoulder and letting her know, but I didn't. She had one of those Do Not Disturb faces on, and I figured, maybe she does know, and maybe she likes having her body in a display case of a dress. Or maybe someone had already pulled her aside and she'd be irritated and embarrassed by the additional heads-up. But ever since, I've felt a little badly, like I should have said something.
So my question is: would you have approached her and told her that you could see straight through the back of her dress? And/or have you ever seen something similar? If so, did you say anything?

I don't think I would want a stranger to tell me that. Too embarrassing. Of course, showing everything to the world is too embarrassing too, but I stick to my original answer of no, I wouldn't tell her.
Posted by: -R- | June 03, 2009 at 10:29 PM
I'll tell anyone just about anything, but I wouldn't have touched this one with a ten foot pole.
She knew. I know, you know..she knew alright.
Posted by: Leigh | June 04, 2009 at 12:14 AM
I wouldn't have said anything to her, for fear that she knew and was perfectly fine with it. However, if I ever make a similar mistake, I hope and pray someone would tell me.
Posted by: H | June 04, 2009 at 12:28 AM
Actually, I probably would have said something. Maybe tapped her shoulder and said, 'I hate to bother you, but in this light, your dress is almost see-thru and I wanted you to know.'
Yes, embarassing for me and embarassing for her, but I'd never see her again.
Posted by: Dianna | June 04, 2009 at 08:20 AM
I wouldn't have said anything, mostly because if I were the one showing my unmentionables, I'd either (1) have realized it (red faced) by the end of the day and was counting footsteps until I could be back in jeans OR (2) if I HADN'T realized it, I'd rather not know, since learning that at the END of the day would mean all memories of that day would be tainted by embarassment.
Posted by: Mar | June 04, 2009 at 09:40 AM
I wouldn't have said anything because I sure wouldn't want someone to say that to me. I'd rather be ignorant.
Posted by: Kate | June 04, 2009 at 01:39 PM
Whenever I see those effortlessly stylish people, I yearn to join their ranks. Not if my rear end has to be on display though.
I probably wouldn't have said anything to her either. It's just not as obvious as a hunk of spinach between the front teeth.
Posted by: Moose | June 04, 2009 at 01:47 PM
I wouldn't have said anything either but that's only because I live in New York too and I just assume that sort of thing is intentional.
Posted by: S | June 04, 2009 at 02:07 PM
Because I am a country girl who moved to NYC in her mid-forties I do tell people and get the weirdest looks. This lady, though, I would have left alone. She knew. I have seen women with completely see through white dresses more than once. I always assume they are doing it on purpose. Oh, well...maybe if I had the bod I would do it to. (Not really.)
Posted by: JudithNYC | June 04, 2009 at 05:18 PM
She totally knew. People like that are calculating. I'm sure she was quite proud of showing of her rear :-)
Posted by: Julie | June 04, 2009 at 08:23 PM
I would have kept schtum, definitely. She knew I am sure of it. If she was that cool she would NOT not have known!
Posted by: Debbie in the UK | June 05, 2009 at 07:24 AM
I probably wouldn't have said anything.
Spinach in the teeth, tag sticking out, toilet paper on the shoe? Those I'll point out. But a see-through issue that MIGHT be a conscious choice? I'll leave that alone.
Posted by: lizgwiz | June 05, 2009 at 11:00 AM
I wouldn't have said anything because I'd be worried she'd roll her eyes and say "Duh!" The black thong makes it seem On Purpose, and I think my comment (coming from someone in jeans and an Old Navy t-shirt) would sound critical rather than helpful.
Posted by: Swistle | June 05, 2009 at 03:59 PM
I want to be effortlessly stylish (*whines*)!
I probably wouldn't have said anything....only for fear that I would embarrass her.
Posted by: danielle | June 18, 2009 at 11:31 PM
I know I'm eons late with this, but I always remember my mother telling me not to tell someone about a problem unless you or she can fix it immediately, that is, if someone has a run in her stocking, she knows, only tell her if you have a package of brand new stockings in your purse to offer her ... along the same lines, spinach in your teeth is fixable immediately. "I can see your bare bum" falls into the keep quiet category unless you had a brand new outfit or slip to offer .... You did the right thing, although I'm sure the image haunted you all day, it would have me!
Posted by: kath | September 01, 2009 at 08:34 PM