What To Wear On A First Date For Men – And Why It’s Critical For Your Finances

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Let’s get one thing straight, this is not a fashion website, but what to wear on a first date for men is a topic worth looking into – for the sake of your finances. Yes, what you decide to wear on a first date could have long-term financial implications.

It’s no secret that dating is hard, but it can also be a really expensive exercise if you end up with someone who isn’t a financial match for you. One thing I’ve noticed is that we spend so much time focusing on compatibility in other areas – hobbies, spirituality, and what kinds of shows we’re into – but hardly ever finances from the get-go. That needs to change.

First dates are hard, dating someone who isn’t a good match for you is harder, but marrying that person is even harder! So, when deciding what to wear on a first date, you need to keep that in mind.

Deciding on what to wear on a first date is actually more important than you may realize, you know what they say about first impressions, right? Before you even open your mouth to say hello, your date will already have developed an opinion based on your appearance. So, you need to make sure that it is a true representation of you.

So today, I want to talk about what to wear on a first date for men to make sure that you attract the right people. I’ll admit, finance talks are awkward on a first date, so an easy way to cross that bridge is to make sure what you look like (and talk about) matches you. Be yourself, right?

What NOT to wear on a first date

So, to get to an answer to what to wear on a first date for men, perhaps a good starting point would be knowing what not to wear. Firstly, don’t wear things that make you look like someone you’re not. If you show up in fancy clothes, driving a fancy car, then you’ll attract people who like that.

You know what that means – once you’ve set that bar, you’ll be stuck keeping that lifestyle up forever, ruining your chances of great finances. As someone who’s very focused on the numbers and financial implications of everything, this is why what to wear on a first date for men is a topic I had to dedicate some time to.

If you want to display that you like throwing money around and are willing to do so for the rest of your life, that’s fine. But get off my site. (Just kidding, all are welcome here.) That means:

  • Avoid designer clothes
  • Avoid suits
  • Avoid fancy and uncomfortable shoes. 

Yes, you may have all the money in the world, but you don’t have to show that immediately. Oh, and another thing – don’t wear too much cologne!! When we think about what to wear on a first date, we generally only ever think about clothing. But practically bathing in your cologne can be so off-putting and borderline tacky, so please, don’t do that.

What to wear on a first date

So, let’s get to the purpose of this article now – what to wear on a first date. The way I see it, you should wear something that represents you and your goals. That way, it becomes an honest representation of who you really are. 

For example, if you want to lead an adventurous life, wear nice, outdoor-inspired clothing. This will set the stage for the kinds of dates you’d like to have in the future, and paint the picture that you’d rather go on free hikes than upscale dinners out. 

We’ve already established that what to wear on a first date should be something that best represents you. The last thing you want to do is show up in a suit and tie, and then be uncomfortable the whole night because you’re actually ALWAYS in your gym gear!

You still want to make an effort in your appearance, so make sure it’s a step above what you’d normally wear. I mean, your date probably made an effort for you, so at least show you care. That means:

  • If you’re a gym guy, don’t wear your workout gear, but maybe a T-shirt under a blazer with sneakers, or a henley that shows off that you’re fit. 
  • If you’re a traveler or a backpacker, wear your “I take these everywhere” jeans, a solid button shirt, and simple boots. 
  • If you’re outdoorsy, make sure you don’t show up in muddy hiking boots, but wear something freshly-washed and coordinated. 

Here are a few options that look good in any setting, say you made an effort, but don’t set the bar too high: 

And here are a few staples that will always look good:

Henley ($18-$24)

Boots ($50)

Why portray your goals on a first date

If you are on this site, you’re most likely already a major catch already, but that means it’s probably hard to find people who are a good match for you. Trust me, I know. So, get your clothes to help you. What to wear on a first date is a visual depiction of the kind of life you lead and the things that matter to you.

If you match to the wrong person, and you marry them, it might be the most costly mistake you’ll ever make! Also, if you wear your money on your sleeves, you might end up attracting people who just want your money. That’s no good at all either.

What to wear on a first date is the starting point that determines whether you’ll spend the rest of your life building on your current wealth or teaching your spouse the basics of money. Honestly, I can’t think of anything more tiring and annoying than the latter.

It’s one thing to have to teach your kids financial principles – I actually like that and think all parents should – but it’s another thing if your spouse is just as blank as your kids. That’s very worrying.

Personally, I would hate to be with someone who thinks money grows on trees, splurges on absolute nonsense, or worse, someone who simply thinks a budget is a target of what MUST be spent.

I’ve said this before and I’ll say it again, marrying someone who isn’t financially compatible with you could be the most expensive mistake you’ll ever make. So, make sure you appear as yourself from the get-go, to make sure that you attract the right person.

TL;DR – What to wear on a first date for men

  • Finance talks can be a bit awkward on a first date, but your clothing can set the stage for what to expect
  • The last thing you want is to end up with someone who’s a financial misfit for you – that can be extremely costly in the long run.
  •  What you wear on the first date will set the tone, so wear something that is a true representation of you and your goals, while still showing that you made an effort. 
  • The last thing you want to do is attract someone who is only attracted to your money, so don’t go flaunting it around!

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