Dating a Classy Girl? Here’s How to Not Blow It By the Clothes You Wear

So you finally did it. You finally got a date with a woman who doesn’t spend her weekends in the bottom of a Cosmo glass or yell “Wooooooo!!” when one of her friends walks in. It’s about time. You’re on your way to being all grows up.

But now it’s time to take a long, hard look at your wardrobe situation—because while most guys have a go-to date outfit (or two), she’s not the type who’ll stick around a guy who habitually dresses like a bum. And I’m not even talking backwards baseball caps and cargo shorts at dinner. You can add pleated khakis and anything by Ed Hardy to the list.

The problem is, we guys don’t often have a fashion role model to follow when coming up. Dad isn’t always the best choice… especially if he’s an office drone and high style isn’t a job requirement. So we tend to dress like our friends. And a lot of times this is unwise.

The problem with this distressing lack of education we get when it comes to clothes is: Dressing well is almost as important to impressing a woman as being well read and knowing what to order at fine restaurants.

Good and Bad Fashion Role Models

When it comes to looking for clues on how to dress, we have few if any real role models, so the first place we typically turn is men’s fashion magazines. Again, this is—in many cases—unwise.

Have you ever really taken a look at how they style those poor bastard male models in these magazines? High style suits the average guy would never wear, or can afford, and layers and layers of clothes and accessories that are out of place in most social situations. It’s a rare sight to see someone dressed in a bold plaid suit, bow tie, and a scarf at a grocery store.

Let’s face it, male models don’t decide what to wear—they’re paid to wear certain brands or styles at the demand of the style editor… a guy who has the unenviable job of making men’s fashion look exciting every month. Hence, the sometimes over-the-top outfits that would make almost any guy look ridiculous on a date at a coffee shop. (Even GQ, the granddaddy of men’s fashion has a section they ran called “GQ Regrets” featuring some of the most outlandish outfits they slapped on the pages of the magazine.”)

The tip here is to use what you see here as ideas, inspirations—and tailor them to your own personal style. See what cut of pants are in style (hint: lose the pleats and wide bottoms), what patterns are popular on dress shirts (checks and stripes still rule, but dots and tight patterns are moving up), and adopt what works for you.

Mirror A Fashionable Celebrity

Many celebrities have a much more natural style. (Think movie star, not rock star.) So, if you’re looking for a guy to pick up some style sense from, check out a guy who you want to mirror while he’s on Kimmel’s or Fallon’s couch. Clooney always looks good whether he’s at a premier or just out grabbing a bite. Something your new girl would appreciate in you. If Goerge’s style is a little too mature, check out Justin Timberlake. JT makes an impression even in a tshirt and jeans. You can also search Google images or visit celebrity-focused blogs to get an idea of how top male celebrities dress. (And ONLY to get an idea of how they dress… Who cares they’re cheating on their wives with.)

Stick to Apparel Brands

There’s another solution to keeping it classy, and that’s to find an apparel brand you like, that fits your lifestyle, and stick with it. When it comes to quality apparel brands, there’s no end to the choices available: Ralph Lauren, Tommy Hilfiger, Tom Ford, Abercrombie & Fitch, and Hollister are all immensely popular, and give you choice at both ends of the price spectrum. Lately, preppy brands are back, with a “dash” of California or West Coast style (aka, West Coast Prep), that could also really help a guy who wants to dress to impress but still wants to keep a sense of kicked back, west coast lifestyle. You can impress without looking too uptight.

Putting it Together

It really isn’t that hard to dress better, with a sense of style. The trick to putting it all together is to have a look in mind, borrowed from your favorite celeb or adopted from magazines, make it feel authentic to you, and wear the hell out of it.

[Image: Antonio García Rodríguez]