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First Date Outfit Ideas for Guys: Dressing To Flirt, Vibe, & Love

First Date Outfit Ideas for Guys: Dressing To Flirt, Vibe, & Love

First Date Outfit Ideas for Guys: Dressing To Flirt, Vibe, & Love

If you’re like any other single, science-believing, COVID-fearing American male you probably haven’t been going on a lot of dates this past year or so.

That’s because COVID-19 is a bit of a cockblock.

And even though at the time of writing this, there are still plenty of states experiencing surges there are other states and pockets of the US that have the disease under control — or at least controlled enough to start dating again.



If you live in one of these places you’re probably ready to awaken from your romantic hibernation.

However, as you’ll soon find out, your romantic skills are a bit rusty and in need of oiling.

One of the aspects of dating you’ll need to familiarize yourself with is how to dress, especially how to dress for a first date.

Look man you’ve been attending meetings pantless for over a year now. Dressing to impress hasn’t been a priority of yours for a while now.

first date outfit ideas

To get you back in the spirit of using your clothes to send a message we’ve compiled tips, tricks, and the best first date outfit ideas for guys to get you back out there.

First Date Outfit Ideas

When it comes to first date outfits, there is no one size fits all outfit.

At emlovz, we recommend clients spend no more than $10 and no longer than one hour on a first date. We advise men do this because if they’re following our MegaDating rules, they’re likely going on various dates a week. If that’s the case they probably don’t have the time or funds to go on pricey, long-lasting first dates.

Not to mention why in the world would you agree to spend $150 and four hours with a complete stranger?

This being the case our clients generally go on either active or super casual first dates.



Common first date ideas include:

— Running

— Cycling

— Sunset drink at the beach

— A quick beer after work

— Jaunt around the park

— Yoga

— Coffee at an independent coffee shop

You may not realize it but there are ample first date ideas at your disposal.

The advice and first date outfit ideas we’re about to impart should be taken with a grain of salt. Use common sense when dressing for a first date.



A jog in the park doesn’t call for Sperry Top-Siders and a polo.

If you’re going on a more casual date

Stand Out By Contrasting

When you’re dressing for your first date in over a year, it’s best to get back to basics.

That means contrasting articles of clothing.

What exactly does that look like?

Something like this.

first date outfit ideas

However, it must be noted that there’s a difference between contrast and clashing.

Contrast is simply pairing colors that are aesthetically pleasing together.

If you keep moving that contrast dial to the right you’ll get a clashing outfit, something that looks like this.



first date outfit ideas

You’re not auditioning for a Willy Wonka remake.

Wear clothing with muted colors and pastels that offer subtle contrast.

When In Doubt Black It Out

Chances are if I were to storm your closet Room Raiders style, I’d likely find a fair share of black outfits.

I say that not because I think you’re some screamo fan whose style hasn’t evolved since he went to his first Warped Tour festival, but rather because everyone owns at least a few articles of black clothing.

first date outfit ideas

Going all black is the safe play.

You don’t need to worry about mismatching or clashing colors.

You also don’t need to fret about buying a whole new outfit for your upcoming date.

When in doubt, go all black.



Know What Colors Complement Your Skin Tone

Maybe you want to spice things up.

If you’re looking to add a bit of color to your first date outfit, first figure out what colors complement your skin tone.

Here’s a quick rundown for you:

Pale: Grey, brown, burgundy, bottle green, navy, and bolder shades of blue.

Olive: Luckily most colors work for an olive skin tone, however, you’ll best be served by colors that are either a little brighter or darker than the middle ground. Shoot for pale beige rather than light sand if you’re opting for neutrals, or opt for a more ambitious shade of purple instead of mauve. The lighter color palette should work in your favor.

Dark: The darker your skin the more freedom you have to rock just about any color you want — except brown. Feel free to don bolder colors such as jade green or cobalt blue. Feel free to dress in vibrant colors that really pop, just be sure they don’t clash.

Make Sure It Fits – First Date Outfit Ideas for Guys

There are no doubt a number of shirts you have in your closet that you haven’t tried on in well, a while.

Before choosing a winner you should make sure the shirt fits snugly.

What’s a snug fit look like?

Allow me to illustrate.

first date outfit ideas



The most attractive style nowadays is a snugly fitting shirt.

You don’t want it to be so tight that if you lift your arm the shirt will rip or too loose that there are pockets of air within the shirt.

first date outfit ideas

As far as your pants are concerned you don’t want your pant leg coiling up at the bottom of your pant. If that’s the case you can either find a new pair or roll up the bottom of the pant leg and show off your socks. This only works if you have the right sock/shoe combo.

first date outfit ideas

What Doesn’t Look Good

We’ve been talking a lot about the dos of a first date outfit idea, but now let’s talk about the donts.

first date outfits

Loose-fitting clothing, bacon t-shirts, and dirty white kicks are all no-gos.

So are high-waters, graphic-tees (depending on your audience), and vizors.

Don’t get me wrong I don’t want to strip you of your individuality, but I also want you to see this girl again.

Ditch t-shirts with slogans or giant company logas slapped on the front. Avoid brightly colored t-shirts (or even t-shirts in general).



For most first dates you don’t have to dress to impress, but you do have to dress to make a good first impression. That means giving a damn. It means wearing an ironed button-up shit that fits snugly and complements your skin tone. It means wearing clean shoes and spritzing yourself with cologne or at least remembering to wear deodorant and to brush your teeth beforehand.

The Ideal First Date Outfit for Men

You may still be at a loss as to what specific items would make a good first date outfit idea.

Here they are.

outfit ideas

Again when in doubt simplify things.

A solid and easy to put together first date outfit consists of a henley shirt, chinos pants, converse shoes – no dad shoes.

outfit ideas

Look, first dates are already pretty nerve-racking. The last thing you need to do is fuss about what you’re gonna wear and ultimately wear something that you don’t feel comfortable in.

Keep it simple and effortless, while maintaining a sense of style.

The style we see above is perfect for a rather relaxing date at a cafe, billiards hall, farmers market, or beach.



But what if you’re going on a more active date?

Styles For Active Dates

Finding an aesthetically pleasing getup for a non-active date is difficult enough.

So how do you dress for an active one involving sweating, red cheeks, and B.O.?

emlovz’s celebrity stylist Hailey Tessem has some ideas for that (in fact just about all these ideas are hers).

first date outfit ideas

You don’t need to throw on your gouache New Balance running shoes and flamboyant running shirt.

Instead, stick to black and white, keep things simple, and don’t shy away from athleisure wear.

Regardless of the first date activity, beauty trumps functionality.

active date outfit ideas

Fancy Smancy

For the most part I recommend going on a first date that lasts no longer than one hour and is active.

However, this is generally recommended if you’re going on a date with someone you’ve never met before.

But perhaps you’re asking a co-worker, friend, or woman you already have a relationship with on a date.



If this is the case you already have a decent connection with this person and are looking to invest in them.

Perhaps that means you’ll want to go to a fancy restaurant, take a day trip, or do something a bit more high-society than grab a coffee.

If that’s the case you’ll want to alter your style accordingly.

third date outfit ideas

There are plenty of items you can play with to create the perfect fancy/leisurely ensemble.

Here are some more fancy first date outfit ideas for you to play around with.

fancy date outfit ideas

But where exactly can you find all these items?

outfit ideas

These are all higher-end (although not luxury) brands that offer a wide array of attire that would up your first date outfit game big-time.

If you’re still struggling to pick out the perfect outfit, hit us up and we’ll walk you through what to wear to woo any first date.

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