How to Dress for Success on a Date

It’s date night — which means it’s time to face that always-dreaded question…

What are you going to wear?

Should you go casual? Formal? How casual or formal? Blazer and tennis shoes, jeans and loafers?

Then there’s accessories — are rings too gaudy? Is a 42mm watch too big?

And let’s not even get started on color wheels and skin tones…

So here’s what you should consider when dressing for success on a date:


Where is the date taking place? You’re not going to wear the same thing on a coffee date that you’d wear to a bar, and definitely not the same thing you’d wear on a hiking date.

What might be appropriate for one venue — shorts while hiking — might look hopelessly tacky somewhere else — like at that upscale cocktail bar.

If you’re unsure about how best to blend with the locals then consider scouting out the venue beforehand and seeing what catches your eye.

You want to be careful not to dress just like every other guy there — remember we want crazy, not ordinary — but you also don’t want to look like you took a wrong turn on your way to a costume party.


If you’ve spent any time at all learning about men’s fashion then you’ve probably heard this before, but I’m going to repeat it one more time — because fit truly is king.

In fact, a good fit is so important that you can even violate the other style rules to follow this one.

For example let’s say you have a date at that classy cocktail bar. God only knows how it happened, but somehow you’ve ended up with just two clean shirts in your closet…

(You really need to be more on top of laundry)

…an old white tee and a crisp black button-down.

Normally the button-down would be the go-to — but when it comes to generating crazy attraction we throw normal out the window.

Because if that button-down hangs off your body like a muumuu on your grandma while that T-shirt clings to your pecs like it was painted on then the choice is obvious…

You want the one that actually fits.


I know I just got finished saying that fit is king…

But comfort confidence might be even more important.

Because if you don’t feel comfortably confident in the clothes you’re wearing, if you’re awkward and self-conscious, it doesn’t matter where you are or how well it fits.

I’d rather be dressed in a stained T-shirt, ratty jeans, and beat-up sneakers in Manhattan’s nicest bar if it means I can be suave and confident.

Because there is nothing, and I repeat nothing, that women are as crazy attracted to as a man’s confidence.

Which is why I always use a secret weapon…

One that most men only use as an afterthought — if they use it at all.


That’s because a high-quality cologne is about more than just smelling good (that’s what a shower and deodorant are for).

You want a good cologne because women are scientifically proven to choose a man based on his smell.

So when I spray on the right scent I can instantly feel myself getting more confident in my own skin, because I know that just by being near a woman I can drive her crazy with attraction.

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