Guy Dress Code: What to Wear For Every Dating Occasion

When it comes to dating and fashion, you can be sure that your lady friend is going to pull out all the stops. She’ll check Pinterest for ideas, put on a mini-fashion show for her roommates, decide on an outfit, then change it, then change it again. Bottom line: she’s out to dress to impress, and unless she’s a complete fashion disaster, she will.

But what about you, sailor? What are you going to wear? Because, as I’m sure you know, when it comes to dating, pulling on your fave pair of jeans and a ratty Led Zeppelin tee ain’t going to cut it when you’re courting a woman (you are courting her, right?).

When you’re dating a woman, you got to dress like a man. You have to dress like you’re in it to win it because that’s the only way she’s ever going to take you seriously on a first date. Once you pass that haute hurdle, there’s even more dress code decorum to follow. Like making sure her friends don’t think you’re a sweatshirt-wearing schlump, and meeting her parents and going to fancy shindigs and having to wear real grown ass man clothes, like a suit and shit.

Dressing date code might seem daunting, especially to those of you who still abide by “if it still smells good, I’ll wear it” philosophy. That’s why I’ve enlisted two of Toronto’s top style consultants, Suzanne Colmer of Your Shop Girl, and Kara Brownlee, to help you dress fly for a guy on every dating occasion.

Do’s and Don’ts on a First Date

First off, no woman wants to date a man who spends more time getting ready than she has. So, you want to make it look like you’ve made some effort, but not too much effort. Like, you thought about your clothes, but then forgot about them. Got it?

Okay, to help you out, Brownlee suggests getting your shoes polished and wearing fitted jeans (“Don’t wear your holiest pair of jeans that prove your recent weight loss,” she says). Also, don’t wear your lucky underwear (‘cause they’re probably fugly and not as lucky as you think) but “do wear something soft like cashmere,” Brownlee recommends, because “she will be touching you all night. Trust me.”

You’re Hanging With Her Friends for the First Time

You know it’s pretty much “ho’s before bros” so Colmer’s dead-on when she advises, “Don’t underestimate the friends. They can be more judgmental than the parents and have an even bigger influence over her decisions.”  Uh-oh. So, what’s your game plan to win them over?

“Pull out the big guns,” says Colmer. “Accessories are a great way to look like you put some thought into getting dressed in the morning. A great scarf, matching belt, and shoes or a cool watch will speak volumes. Think Brad Pitt or David Beckham more than Johnny Depp though – no body wants their friend to date a guy who wears more bracelets than her. “ No, although a tat that says “Wino Forever” is forgivable.

It’s That Time: You’re Meeting Her Parents

You’ve got your “how we met” story straight and practiced your firm shake. Now, it’s time to look in the mirror for one last look. What you shouldn’t see are “jewelry or graphic tees,” says Brownlee. “Stay away from anything controversial. Assuming you like your new lady and her dad isn’t going to like you anyway, stay neutral and polite.” Just adding a classic shirt, blazer or tie will do, according to Colter. “You don’t have to sacrifice your style personality,” she says. “But you do have to show off a 2.0 version of it for the parents.

Things Are Getting Serious and You’re Going to More Formal Occasions, like Weddings

Time to bring your A-game, fellas, which, in this case, means a really sick suit. Colter recommends a grey or navy suit rather than a black one (don’t want to be too penguin-y, I suppose).

“Once you have the suit, check that the shirt and tie match,” advises Colter. “If you are mixing patterns, coordinate the colour of the patterns or match the patterns. In other words, a red checked shirt can be worn with a red polka dot tie or a red checkered shirt could be paired with a blue checked tie.” Basically, the more similar they are, the easier it is to wear.

And remember guys: “There is nothing yummier than a man in a well-tailored suit,” says Colter.

And The Biggest Fashion Faux-Pas That Would Break A First Date

Brownlee keeps it simple, but straight-up (and speaks for pretty much all females) when she says, “I’m a firm believer in being yourself. I mean, I’m going to figure it out sooner or later, so why not just get it out of the way? However please don’t: wear socks and sandals; have labels on everything  (I don’t want to read your outfit); bring an empty wallet.  It might be 2014 but I’m still a lady and my Dad wouldn’t approve.”

Amen, sister.

Brianne Hogan is a freelance writer based in Toronto, something of a humorist, and considers herself more Bridget Jones than Samantha Jones. Though she won’t reveal which parts, she will admit to liking emotionally unavailable men and drinking lots of wine.  You can follow her on Twitter  @briannehogan.
Photo courtesy of Mathieu Jarry.

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