What Not to Wear on a First Date

• No flip flops. Summer or no summer, you don’t want to write yourself off as a beach bum, or a 17 year old high schooler, or, worse, a man with surfing aspirations but absolute lack of the beachy environment. Why do Toronto men wear flip flops? We’re not in Miami, and I’d rather see your toes adorned by a fine pair of Adidas Supers or Nike Air Force 1’s. Go to Nice Kicks for sound advice. The right pair of shoes can go a looooong way.

• Uggs. To return to the topic of shoes. If you’ve met in the winter time, and the pretty snow is sure to freeze your toes, uggly uggs are not a solution. NOT a solution. Surely you must possess other, real kind of shoes if you’ve graduated from at least a high school.
• See-through / mesh stuff. Sure, this American Apparel dress is smoking hot on maybe a girlfriend of four months (and maybe inside your abode, depending on how conservative you are), but this certainly doesn’t befit a first date.

• While you’re at it, cut out the PVC.
• Sweat pants – however cute that may look on a girl, sweat pants ooze laziness, lack of style, general boredom and zero imagination. Not a great first impression.
• Lululemon wear. Unless your date is at a hot yoga studio, do not try to pull off the semi-athletic or semi-yogabend streak of yours. Take the extra minute or two to get out of your skin-hugging uniform.
• On the opposite spectrum, you might intimidate your date with a tuxedo or a complete suit. As much as I like a sharp-looking man, the less enthused ladies may have a spill over a possibly intimidating appearance.

• Poop hat does not deliver the right kind of a message.

• Assless chaps. While MJ says that Assless Chaps are for only the trendiest trend setters. and “Cool hunting begins in the butt” (roaring laughter please), the majority of humans can’t pull it off. So don’t try it. Not even at the gay parade!
  
• Ed Hardy wearables. Someone just commented on how innocent I am with my lack of thorough knowledge of the Ed Hardy SS 2010, I say, thank god. By now I’ve researched what I’ve seen on the streets. And please. DO NOT WEAR THIS:

Your suggestions? What should you not wear?

Takeaway: the best thing you can do is be yourself. Dress comfortably. Perhaps choose a little more subdued colors than you would normally go for. Accessorize tastefully. Remember that less is more (in terms of colors and accessories, not the amount of clothing you wear). Do not hang out at the extremes of “max relax” (sweatpants) or “uppity up” (full on suit).