There I was one night, peeping through the hole in the door at what was supposed to be my date for the evening.

I met him at a boat party but I couldn't remember what he looked like – there was free wine, and it was dark, so pardon me for being tipsy. So I'm looking at this guy, wondering if I could possibly claim to have the runs so I could cancel the date. Don't ask if it was really that bad. Of course it was.

I paused after opening the door as the full effect of this walking fashion disaster finally dawned on me. What could have possibly been so bad? Ugly shoes? A stained shirt? No, this went beyond poor hygiene. Imagine this man – a bit chubbier than I recalled, damn that open bar! – with skin worthy of an eighth grader . His hair was an homage to Kirk Cameron and his clothes weren't so far behind. And this was before the days of irony. His jeans were acid-washed and, of course, ripped at the knee. His matching denim jacket obscured whatever was on underneath. I don't think I even made it down to the shoes but I'm sure they weren't pretty. The rest of the evening went downhill from here, and let's just say as a general rule : never to offer blow to your date unless she's a socialite and you're doing it off her.

The good news is that some of us have a clue and a full-length mirror. To make sure we're on the same page, it's time to go shopping.

First things first: Get a new haircut. Make it cute, make it stylish, but lay off the gel. And don't go get another run-of-the-mill art-and-science ‘do. You're not 17 anymore. There are slews of stylists who can give you just the right head. Just know that a good cut is essential. And if you do need a little product, I swear by Kiehl's Silk Groom or MOP's defining cream , which you can get at pretty much any good stylist. But if I hear another straight man utter either “manicure” or “pedicure,” I'm going to kill him. If I wanted to date a woman , I would.

Next up are shoes. Unless you're donning a tux, ditch the dress shoes. Cool sneakers are the way to be. A pair of black Converse high-tops will still get you laid. Head to Sears (yes, you read right) and grab some for 30-ish dollars, or go totally retro with Royal Elastics . The Zedlans are great, and you can be sure no one else will be wearing them.  If white shoes make you feel like you're in the fifth grade, go for the navy icons. I'd suggest getting them straight from the company to save a few bucks – after all, your date is gonna cost you plenty.

This is so freaking important: Next up are the jeans. The best place is always Diesel, found in Chicago at 923 North Rush Street. Yeah, I know, you'll feel like s ome Miami pretty boy , but damn they make a nice pair of pants. I have yet to meet a man who didn't look hot in them, and with every fit and wash you could ever hope for, they've got your ass covered.

Now it gets just a bit tricky. What goes on top? Her, if you're lucky, but first you gotta impress her with your shirt. A cool tee under an open button-up revs me right up. Apt. 9 has both but be ready to spend some cash. Don't get just any striped shirt, because you need to buy the original, Paul Smith. If you have to go cheap, then go to Urban Outfitters at 935 North Rush Street, but dear God, only if you're under 25.

Now go get her tiger.