Skip to content

What Shoes Should I Wear On A Date For Guys & Why Women Find It So Important

What Shoes Should I Wear On A Date For Guys & Why Women Find It So Important

What Shoes Should I Wear On A Date For Guys & Why Women Find It So Important

A wise man once said you are what you eat.

An even wiser man then corrected him, you are what you wear.

That’s because you’re heavily judged on your appearance. We all know this but psychologists have confirmed our preferences for the bold and the beautiful by naming the cognitive bias we feel when we engage with pretty people; the halo effect.

what shoes should i wear on a date

The halo effect is when we assign beautiful, well-dressed people positive characteristics solely based on their appearance.

A man wearing a sports jacket and Steve Madden shoes will be perceived as smarter, nicer, fill in the trait, than a guy who’s rocking crocs, hasn’t shaved in days, and who is donning a hoodie.

Sure it’s annoying that we live in such a superficial world, but you’re not going to change anyone’s mind by dressing down. To get the job, the friends, and the girl you’ve got to put a little effort into your appearance.

Specifically you should think about what’s on your feet.

What Shoes Should I Wear On A Date?

Shoes are typically the last thing men think about when dressing for a date.

The outfit revolves around the shirt, followed by the pants, socks, and lastly the shoes.

But just because you’re not overly conscious about what you’re wearing doesn’t mean she isn’t.

To complete the ensemble you’ll need to invest a moment to think about your feet.

To give you some ideas, let’s go over the best shoes for men to wear on a date.

White Leather Shoes

First up are white leather shoes.

According to our celebrity stylist Hailey Tessem, white leather sneakers are quality first-date shoes. They don’t look “try-hard”, they’re versatile, and they’re clean (if you keep them that way). Hailey is a Parsons grad that has styled for fashion magazines, ad photoshoots, as well as TV and film. 

She knows a thing or two about looking good.

White leather shoes are casual yet classy, comfortable yet stylish, and are made to make a lasting first-date impression.

But you know what, there are a million white shoes out there, so which should you buy.

Here are a few examples.


Converse are classic, affordable, and will never go out of style.

This is the Jack Purcell. At first glance, they look casual but take a closer look and their leather veneer really brings out the inner class.

Halo effect anyone?

what shoes should i wear on a date

Banana Republic

Normally not known for their shoes Banana Republic has a super affordable, super fashionable pair of shoes in their ranks.

Just remember to keep them clean.

what shoes should i wear on a date

Cole Hann

To kick it up a notch in style, rock these sweet pair of Cole Hanns.

what shoes should i wear on a date

The beauty of white shoes is that you can rock them with anything. It doesn’t matter how colorful or outlandish you dress white shoes will always complement and balance out your look.


You’d swear they’re sneakers.

Laid back yet formal enough, this pair of Vejas will work with any outfit you rock.

what shoes should i wear on a date

Generally speaking, the first two dates are going to be rather laid back.

This is because you don’t know this person all that well and thus shouldn’t go to a fancy restaurant, get dressed up, and spend big on someone you don’t even know.

Chances are high you could be un-attracted to her the second she sits down.

With that said keep the first two dates light.

First dates should last no longer than an hour with no more than $20 being spent.

Second dates should be active.

But what if you don’t want to rock white shoes on a first or second date?

Here are some other options for you.

What Shoes To Wear On A First Or Second Date

Keep it light, comfy, yet classy.

Here’s what shoes to wear on a first or second date.


Allbirds are all the rage nowadays.

Not only are most sustainable, vegan, and super comfortable, but they come in a variety of casual styles.

I love the Wool Pipers but you can easily also rock a pair of Tree Pipers.

what shoes should i wear on a date


Another casual yet stylish shoe are these SUAVS.

what shoes should i wear on a date

They’re comfy, versatile, come in a variety of colors, are washable, dry quickly, breathe, and are super affordable at $76.

Hell, you don’t even have to wear socks with them.


If you want to dress up just a touch more without going overboard I recommend you head over to KOIO and grab a pair of these laid-back, easy-to-wear, leather sneakers.

what shoes should i wear on a date

Third Date Shoes

Casual might be fine for a first or second date but that all changes if she’s lucky enough to make it to a third date.

Third dates are when you go all out.

They’re when you treat her to a nice meal, spend big, and show her how important she is to you.

With that said it’s now time to kick up a classy notch or two.

To do that let’s introduce some leather.

Steve Madden

I know I said it’s leather time, but let’s hold off on that for a minute.

Before diving into the leather let’s talk suede, specifically about Steve Madden’s Erik Grey suede shoes.

what shoes should i wear on a date

Normally when we think suede we think money, over-the-top fashion, and flash.

That’s not the case with these shoes. Coming in at just $70 these are just the kind of flash you need on a third date. Just make sure it’s not raining.

Monk Strap

There’s class and then there are monk strap shoes.

A monk strap is simply a buckle strap instead of laces.

They’re leather, to die for, and don’t get more much classy than this.

These are perfect for the theater, a fancy restaurant, or hey even a gala.

If you dig the strap but want more just get a pair of double-strapped monk shoes.

what shoes should i wear on a date


My personal favorite are a pair of Derby brown leather dress shoes.

They’re simple yet stylish, are comfortable, and can be worn with just about anything and everything.

If you’re only going to have a single pair of dress shoes let it be these.

what shoes should i wear on a date

What Shoes Should I NOT Wear On A Date?

To be fair this is a difficult question.

It really all comes down to:

  • The type of date
  • Who you are
  • Who your date is

My gut reaction is to never wear Vans on a date.

But that changes if you’re on the younger side and are dating a more laid-back skater chick. If you two are hitting the skate park for a first date or attending a concert then maybe Vans are the perfect shoes for you.

That being said, there are some shoes that should never be worn on a first date.

Here are my picks.

Sandals/Flip Flops

A little skin on a first date is fine but toe hair early on in a relationship is a great way to squash any fledgling feelings.

Unless you’re off to the beach for the day cover up those feet.

And if you think a quick fix is to throw on some socks you’d be wrong, oh so wrong.

Sock and sandals or socks and flip flops are a no-go.

They’re obnoxious, show the wrong kind of skin, and aren’t really functional for an active second date (which we recommend).


These don’t need much explaining right?

I mean I know they were all the rage during the pandemic and soared in sales, but the pandemic is winding down and we all have public lives again.

Guaranteed she’ll think less of you if you’re rocking crocs on a first date.

New Balance

Maybe it’s just me but New Balance shoes are the least stylish of all shoes.

They’re bulky, only come in weird colors schemes, and are purely functional. Hell you might as well wear a low-cut v-neck and a trucker hat while your’e at it.

New Balance is only acceptable for active dates.

Designer Shoes

I have to admit that there’s a bit of a double standard when it comes to designer shoes.

Women can rock them for days whereas men just struggle.

This is because designer shoes are almost always outlandish. They’re super difficult to style correctly, flamboyant, and loud.

Only rock these if you’re 100% certain you can get away with them.

But in general, keep the Prada and Gucci in the closet.

what shoes should i wear on a date


Again, read the room.

If you’re in the south, dating a conservative woman that’s into all types of leather, feel free and throw on a pair.

But if you’re in a major city dating a PC-woman that will be annoyed with you supporting the murder of crocodiles to make shoes, leave them in your closet.

Next Steps

Still don’t know what to wear?

Consult with our fashionista, Hailey to understand how to pique her interest with your clothing.

Our program, Dating Decoded also teaches our students how to dress, how to flirt, and how to create a dating profile that outperforms 90% of the guys in your area.

Let’s talk via a 1-on-1 Zoom call so we can better understand your dating goals and show you how emlovz can help you achieve them.

Comments are closed for this article!

Featured Articles