What to Wear on a First Date

Example of what to wear on a first date. A man wearing a t-shirt and blazer

What to Wear on a First Date

At some point we’ve all asked ourselves the question, “What to wear on a first date?” When it comes to a first date, or any date for that matter, looking good, feeling great and dressing appropriately for the occasion is of utmost importance.

My readers are always asking how to feel more confident on a first date, and even if you don’t realize it gents, what you wear is key to this. So, with your requests for more insight on how to be confident and what to wear on a first date, I thought who better to answer this question than my good friend Dave from Irreverent Gent. Dave helps contemplative guys build real, lasting and authentic self confidence.

Check out his article below for the absolutes when it comes to getting yourself ready to hit the town with a female of interest.

Your First Date Attire Will Make a Lasting First Impression

So, you’ve followed Rick’s advice, read his ultimate guide to dating, learned how to ask the right questions, and mapped out the perfect fun, flirtatious and exciting activities for the two of you to do.

There’s just one problem: you have no idea what to wear.

(And while you may be hoping to end the date by getting naked, showing up like that probably isn’t the right way to get your relationship started.)

The good news is that with a little preparation and a bit of forethought, you can easily choose an outfit that will help you look – and feel – well put together, cool and confident.

1. Locate Your Date on the Style Spectrum

When plotting out what to wear on a first date, you want to start by thinking like a real estate agent: location, location, location.

If you’re the one who chose the location of the date, chances are it’s a place you’ve been before. Ask yourself: when you’ve gone there in the past, how were people dressed?

Is it a jacket and fancy shirt type of place, or did the crowd have more of a “jeans and a polo” type of vibe? On the spectrum of “super casual” to “very fancy,” where did most people fall?

If she chose the place for your first date and you’ve never been there, look it up online. How are people dressed in the photos on their website? Are there any user-submitted shots on Yelp or Trip Advisor?

Assess where the location falls on the casual-to-fancy style spectrum and how you expect everyone else to be dressed. This will give you a base-level to work from in plotting out your own outfit.

2. Remember the 10% Rule

Once you’ve got a good idea (or at least a ballpark estimate) of how casual/fancy the place you’re going is, the next thing you want to do is ask yourself this question: how can I dress 10% better than every other guy there?

This is one of my favorite little tricks for dressing well (in fact, I consider it one of the most important underlying principles of style), because, while it’s almost stupidly simple, it’s also incredibly rare. Hardly anyone takes five minutes to think about how they can outdress other guys – meaning you have a golden opportunity to do just that.

If you’re going to a super casual place where most guys will be wearing shorts, a t-shirt and flip flops, step it up by wearing lightweight chinos, a well-fitted polo and boat shoes.

Going to an after-work bar where most guys will be rocking the business-casual uniform of a dress shirt tucked into their dark pants with black dress shoes? Throw on a blazer or sportcoat to take your look to the next level.

You get the idea. Take a few minutes to figure out how to go just one step further than the majority of guys, and you’ll instantly stand out in the eyes of your date.

Pro Tip: One easy way to upgrade your look that most guys neglect – but most women notice – is by wearing nice shoes. For guys, shoes are an afterthought. But women spend a ton of time and money investing in their own shoes, and in turn they always notices ours.

Apply the 10% rule to your footwear and you can bet that your date will appreciate your effort.

3. Put Yourself in Her Shoes*

Have you ever noticed that what guys perceive as being cool differs quite a bit from what girls think is cool?

To give you just one example, I was talking to a female friend of mine a few years back, not long after the movie Crazy, Stupid, Love with Ryan Gosling hit theaters. After seeing that movie, my friend declared that Ryan Gosling had the best body in Hollywood, and all her girlfriends agreed.

To which I responded: “WTF!? Haven’t you guys seen Thor? Or Captain America? Or Hugh (f@¢&ing) Jackman?”

Their reply? Too muscular. Too vascular. Too veiny. Too… much.

I was flabbergasted. Here I was working my ass off in the gym, trying to reach the (probably impossible) standard set by the leading men in superhero movies, and it turns out the majority of women I knew preferred the (still quite fit but much more realistic) standard of leading men in romantic comedies.

And just as men and women have different perceptions of the perfect body, so too do we differ when it comes to questions of style. So don’t assume that just because you think something looks good, your date will agree.

The good news here is that it’s not too hard to figure out what styles women find attractive – or at least, some women find attractive. Head over to the Pinterest page for Style Girlfriend, the men’s style blog founded by Megan Collins and run by women.

They’ve got all sorts of boards and outfit suggestions that can give you inspiration. Choose a few that fit within the context of your date, and either choose pieces of your own that closely resemble what they recommend, or go out and buy some new ones.

*I mean that figuratively. Don’t show up to your date in pumps. (Unless that’s what you really want to wear, in which case, live your life. But you should probably make sure you date is aware of it, and cool with what you’re into…)

4. Express Yourself Authentically

I may have buried the lead here, because this is probably the most important tip of all.

When it comes to dressing well, the most important thing to remember is that your look has to feel right to you.

You can spend hours upon hours researching exactly what other guys will be wearing; figure out the best way to dress 10, 15 or 20% better than them; delve into the minds of women and make sure your choices match with their conception of handsomeness… and still end up looking and feeling like a total poser.

The truth is that nothing looks better than a man who’s clearly comfortable in his own skin – and his own clothes. So if you think a blazer will help you outdress the other guys, but wearing one makes you feel stiff, awkward and dull, then don’t do it.

If you know you should probably wear dress shoes, but you also know they hurt your feet and you’re much more comfortable in sneakers, then stick with the kicks that got you this far.

You want to choose clothes that let you put your vision of your best self forward – not someone else’s vision.

After all, the best way to look good is to feel good. And nothing feels better than knowing that you’re true to yourself.

About the Author

What to Wear on a First date

Dave Bowden is a reformed journalist, award-winning blogger, compulsive joke-teller (not to be confused with a competent joke-teller) and the founder of IrreverentGent.com, where he helps guys overcome over-thinking, escape insecurity and take control of their confidence through self-improvement. You can find Dave at www.irreverentgent.com