Taylor’s Take: Summer Date Style for Guys (Updated!)

Taylor’s Take: Summer Date Style for Guys (Updated!)

How to steal my heart before you even say, “Hi!”
vans, authentic, check, summer date style, summer date

By Taylor Davies | Last Updated: Jun 23 2022 | 5 min read

I need to talk to you guys about summer date style. I have *feelings.*

You know that song “Summer Nights,” from the classic 1978 movie musical Grease? “Summer lovin’, had me a blast! Summer lovin’, happened so fast!” So it goes in song, and so it goes in my imagination every time this season arrives. By mid-May, in fact, I get so amped about a summer romance that I dial my dating app usage to not-cute levels of thirst in hopes of queuing up a relationship with some real *fireworks* around the 4th of July.

Spoiler alert: That has literally never happened to me.

America’s birthday has come and gone, and in its wake? A string of going-nowhere-fast first dates that are serving me only as great inspiration for this week’s Taylor’s Take.

Below, a few hot takes on summer date style:

1. Throw on a short-sleeve button down.

parrots shirt

For an immediate +5 right out of the gate, there’s nothing better than a guy who’s bold enough to flash a little arm in a colorful, irreverent print. It shows style and humor and potentially a little of your tan, too.

If you know anything about me, you know I love Bonobos and their ‘Riviera’ shirt. Want something a little trendy? Go with a camp collar shirt in a fun, irreverent print.

Basically, I’d be expecting you to show up in a chambray shirt or some sort of stripe—which is, to be fair, fine.

…But I’m not looking for fine, am I?

Be amazing, dress amazing let’s “Summer Nights” this thing!

2. Just doing dinner/drinks? Leave the shorts at home.

I know it’s summer and I know it gets hot, but please—save the shorts (and that thigh-full view) until we know each other a little better.

Generally, shorts read a little too casual (and college age-y) for a first date unless it’s an activity. Are we playing mini golf? No? Then no shorts.

And on a more personal note, if you do have great thighs? First of all, call me.

But second of all—I will objectify you, and that can prove quite distracting when you’re trying to explain exactly what kind of finance you do.

3. Stick to just one type of liquor…please?

summer date, summer date style

When I showed up (3 minutes late, natch) for a first date last week, the guy was drinking a whiskey cocktail. It looked great so I ordered the same. When he was finished with that, he ordered a Negroni.

After that? A frozen margarita. After that? Red wine.

I am not kidding.

You guys are savvy adult males, so you know what I’m getting at here—there was no taste level, no swagger. Your drink is an extension of your mood; your personality. Be decisive. Nobody wants a man who doesn’t know what he wants.

4. Consider giving your hair products a vacation!

I’m going to make a bold statement: What your hair does naturally when you get out of the shower and head out into the world probably looks and feels 90 percent better than what it does when it’s beaten into submission with gel or pomade.

The same way that women often retire their hot hair tools this time of year in favor of a more natural, air-dried look, you can do the same! I promise! When it comes to summer date style, I want to imagine putting my hands all up in that mop sometime soon. And if all I can focus on is the potential for crunch or slime… It’s not looking good.

5. Find your Vans, man.

vans, authentic, check, summer date style, summer date

Whether it’s the Old Skool, Authentic or checkered slip-on, I love the look of a guy in a pair of well-worn Vans.

They’re casual and cool and for a reason I can’t quite swipe my finger on (See what I did there?)—sexy. When a guy shows up to a date in a pair of navy Authentics, I feel a sudden little heart swell like, “This guy is for me.”

What I’m getting at here is that showing off your unique style is important on a date. Whatever your “Vans” are in the grand sense—wear them!

Maybe it’s a leather bracelet! Maybe it’s novelty socks! Different women feel that heart swell for different things, so showcasing your unique taste can have huge payoff when it comes to meeting your special someone…

Or the Sandy to your Danny, as it were.


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Taylor Davies splits her time between NYC and Sun Valley. She loves writing about menswear, overpriced martinis in dimly lit hotel bars, and cross-country skiing. Not necessarily in that order.