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What Do I Wear?


New Member
Nov 4, 2006
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Hope I'm not barging in. I figure you guys can help.

So. We met at work: he (~40) supervised a project I (~30) consulted on. We're having drinks at a cozy landmark restaraunt -- at the bar, denim could work, which he made a point to highlight.

Preliminarily, I would date this guy. What he's up to remains unclear though. The fig leaf for this meet up is to "pick my brain" about a business venture. Plausibly so, albeit doubtfully -- based on his office flirtations. On the one hand, I want to communicate availability. So something low-cut? (Boobs: whatever, alas; collarbones: showstoppers.) But then, if the biz pretext is real, I risk folly. Jeans miniskirt with winter tights and boots, instead?


Bill Brasky

Well-Known Member
Oct 31, 2006
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Huh?? Are you sure you're ~30. This post seems to be written by a 16 yo high school girl.


Current Events Moderator
Mar 19, 2002
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Jeans, heels and a nice top. You want to communicate availability, but not sluttiness, so skip the cleavage. Take a look at what Stacey London wears on TLC's What Not to Wear Show.

Jeans are perfectly appropriate to discuss business and if he mentioned it, it's probably because he doesn't want you to be overdressed, because he probably won't be.

You didn't mention where you are located or what type of industry/project? That information would be helpful.

The main thing is, just be yourself. If he likes what he's seen already, he should like you outside of work.


New Member
Nov 4, 2006
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NYC. The project involves a fairly new legal field that I happen to specialize in.

Jeans + heels, good idea. I didn't even think of that because heels lift me over 5'10", and I usually want to minimize attention. But you're onto something -- this guy already knows me, so that's a nonissue.

The real issue, on reflection, is beneath what to wear. Typically my dates are clearly dates and spent at a museum or walking in the park or whatever. I'm uncertain, here, why this guy didn't suggest lunch or at least a more neutral place if he wants to talk just business. Though my instincts lie beneath years of focusing on career, interests, and sports, I'll just try to go with them.

I appreciate your suggestion. Thank you!

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