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by Emerson O'Sullivan III aka FancyLad, for outsideleft.com
originally published: March, 2005
By the time the dessert cart comes around, you'll know if she's sweet on you or not.

Fancylad, outsideleft's own in-house self-appointed style expert answers all your nagging questions on fads, fashion, vanity, style and the gentleman's code of conduct.

My boss just asked me out to dinner. What the hell, is she flirting with me or not? Should I even go? I'm a little interested, but I can see this really screwing things up for me at work later. And who pays?
—James Ariki [San Francisco, California]

What are you waiting for, friend? Go. So far, she's just asked you to dinner—it's a business meeting as far as you're concerned. By the time the dessert cart comes around, you'll know if she's sweet on you or not and you can take it or leave it if things go any further after that. Chances are that she just want to talk shop, but in my experience as an office lackey, it's pretty dicey when it comes to interoffice dating—someone always gets burned. As for who picks up the tab—she invited you so either she pays or the corporate expense account does.

Can a guy wear a suit jacket as a sports jacket? My roommate says yes and he looks kind of awkward trying to prove his point in public.
—Claire Hagan [Dallas, Texas]

Absolutely not. If I had a nickel every time I saw some fratboy in a pair of cuffed khakis and a suit jacket on my way to the office, I'd be knee-deep in tail for the rest of my life. Chalk this up to a bad trend set by a pre-stroke Letterman. Generally, this look never works. If you have a fine navy blue suit, maybe (and that's a big maybe), you can get away with wearing it as a blazer, but a gray pinstripe number and Dockers don't do it for me, sweetheart. A sports jacket was made to go with oddball trousers and jeans. Suits were meant to stay together. Why do you think they call them suits?

I'm in my early 30's and I've always worn my college ring, which is gold. I also just got an incredibly expensive stainless steel watch from my girlfriend as a gift. Is it wrong to wear the gold and silver together? More importantly, is it lame to wear your college ring 10 years after you've graduated from school?
—Curtis Gropp [Boulder, Colorado]

Lame? Nah. Fancy Grandpa wore his U.S. Naval Academy class ring proudly to the grave. There's no real reason to give yours up, unless it's garish (as they sometimes tend to be) or if it's from a college from where you learn to "drive the big rigs." If you're really that worried about the color clash, you could wear the watch on one side and the ring on the other. But look at all those married guys out there with gold wedding bands and steel watches. Do they look worried? (Besides the fact that they're married, that is.)

Need advice? Does it concern fashion? Style? Affairs of the heart? Fancylad shoots straight from the hip pocket. Send him all of your questions to info@outsideleft.com—the intern-monkeys will be sure to pass them on to him.

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