What to Wear on a First Date: How to Feel Confident No Matter What Type of Date You’re On

If it’s been a while since you last dated, you may be clueless as to what to wear on a first date.

You don’t want to look “easy”, so short skirts and tight tops are out…aren’t they?

And you don’t feel like you need to cover up head to toe like a nun…

Where’s the balance here??

Breaking Down What to Wear on a First Date

Sure, what you wear on a first date may be different if you’re in your 50’s then if you are in your 20s. But the key is finding what makes you feel good.

Also, it depends on what sort of first date you’re going on. You obviously wouldn’t wear heels and a skirt if you were going to play mini golf or to the beach, and you’d want to dress up a little if he’s asked you out for a nice dinner.

Let’s look at different date scenarios to help you find the right outfit for each.

Coffee Date

This is the gold star first date: it’s short and sweet, so if you’re not into him after an hour, you can leave. If you are hitting it off, you can stretch it out by going to happy hour or on a walk…or end the date and leave him wanting more.

Great for: meeting someone for the first time from a dating app. 

Because I always urge you to exercise caution on a first date — particularly if it’s with someone who you only know online — a date in a busy coffee shop is a safe option to get to know him.

And because you’d usually get coffee in the morning or afternoon, you don’t have to worry about things getting too romantic if you’re not sure you want them to. Most guys want the cloak of night around them before they’ll make the first move, and may not try to kiss you in a busy parking lot after the date…unless it went really well and you’re communicating that you want him to!

What to wear: something casual

You don’t want to overdress and look like you’re trying too hard. Pick something kind of business casual.

Jeans are perfectly appropriate for a first coffee date.  You can dress them up with heels or sandals…or give a casual vibe with some funky sneakers.

Add a slightly dressy blouse and some light jewelry, and you’ll look smashing.

So here’s a question I know you’re going to ask about what to wear on a first date:

Cleavage or no?

A little is okay, but since it’s daytime, don’t go overboard. Leave an air of mystery about your body while still wearing a flattering top.

Drinks

This is the evening version of the coffee date. It may last longer than a coffee date, and because you’re not doing something else (eating, taking a cooking class, playing mini golf), you can focus on getting to know your date over drinks.

Great for: meeting someone from a dating app who you’re fairly comfortable with (you’ve chatted for several days or weeks). You feel reasonably sure you can trust him.

Tip: drink slowly! The last thing you need on a first date is beer goggles! It’s all too easy if you’re nervous to guzzle down your vodka soda, but realize that this can put you in a vulnerable position. Not only will you be more attracted to him when you might not be otherwise, but you may also do things you wouldn’t do sober, like go home with him.

And beer goggles aren’t just a myth! In a study published in Alcohol and Alcoholism, researchers found that alcohol influenced the perceived attractiveness to other people. So if you didn’t find him attractive in the first five minutes, but an hour later you do (and it’s not because of his winning personality), realize that alcohol may have played a small role in your attraction to him. Wait and see how you feel about him on a second date.

What to wear: depends on the venue

If you’re going to a brewery or beer pub, opt for jeans, cute sneakers or sandals, and a casual top. If you’re having drinks at a fancy restaurant bar, choose a slightly casual dress (like a sundress in the summer) or dressy pants and a nice blouse.

Dinner

While it seems like more first dates are going out for coffee or drinks, dinner is a great option too. Good dinner first dates have a way of stretching on for hours! And they provide a great way to learn about the man you’re out with.

His choice of restaurant can tell you a lot (though don’t judge him harshly if he chooses a little taco stand for your first date; that can be fun too!), as can how he treats the wait staff. Does he go adventurous in his meal selection, or play it safe? Have fun analyzing your date over a great meal!

Great for: a man you’ve already met and know you’ve got chemistry with. While sure, you can go out to dinner with a man you’re meeting for the first time through a dating app, I more often hear from clients about dinner dates with men they met organically. Maybe that’s because both of you already know you’re attracted to one another, whereas with an online date, you’re still trying to figure out if you have chemistry together and want to opt for a shorter date.

What to wear: dress up just a little

If you love wearing dresses, go ahead and rock one (even if you go to a taco joint! You’ll be memorable). Otherwise, go for nice pants and a dressy blouse.

You can wear a bit more jewelry than you would on a daytime date, but don’t go overboard. Take Coco Chanel’s advice: “Before you leave the house, look in the mirror and take one thing off.”

Hike

If you’d rather be active than sitting and sipping on a first date, a hike is a great way to get to know someone. Make sure you agree on a hike that you are both capable of; this is not the time to either bite off more than you can chew (and need to be airlifted home) or try to show him up with your awesome Kilimanjaro skills.

Great for: active types…or if you’re nervous and uncomfortable sitting and talking with a man you don’t yet know.

What to wear: activewear

If you don’t mind wearing something form-fitting on a first date, go for yoga pants for ultimate comfort. If not, wear athletic shorts, hiking pants or capris.

Above all, wear sensible shoes! There’s no point trying to be cute if you risk twisting your ankle in the wrong shoes!

Wear a hat, either to protect your face from the sun or to keep your head warm…or both.

This is not the time to wear cute jeans or a complicated top. If you wear comfortable clothes on your hike, you won’t be stopping to fidget with them (and yes, he’ll notice).

Tips for What to Wear on a First Date

via GIPHY

You may think you need to wear tight, low-cut clothing to attract this man, but trust me: you’re better off wearing clothes you feel comfortable in. If you feel good in your clothes, you will look good in them. Plus, you want him to be attracted to who you are, not what you wear.

Try on the outfit before going out in it, especially if it’s brand new. See if it pulls or constricts you anywhere. If so, don’t wear it.

Communicate Confidence

Consider wearing red! Studies show that the color is attractive to others, and of course, because it’s so bold, it exudes confidence.

When it comes to deciding what to wear on a first date, be bold in one category. Go for patterns on your blouse, a chic design, stand-out jewelry…just not all three! You want a subtle touch that shows you care how you are put together…but you don’t want to scream that message.

A Word on Makeup

In terms of makeup: go with what you’re comfortable with. There’s no need to wear more than you normally would if you were going out with the girls.

Look for long-lasting lipstick so that it doesn’t all melt away while you drink or eat…and in case the date ends with a kiss!

Pay attention to your nails. While it’s not necessary that you go get a professional manicure, you should at the very least make sure they don’t look dirty.

Now for Shoes

Wear heels if you’re short and he’s tall…if you know that he’s short and you’re tall, skip them so you don’t intimidate him.

Don’t wear shoes that will give you a blister or that you can’t walk in. There’s nothing sexy about a man having to take his date to the drug store to buy flip flops so she can walk if her shoes have crippled her!

Take the Local Vibe Into Consideration

People in San Diego rarely get really gussied up. You might throw him off if you wear too fancy of a dress for a drink date…and he’s in cargo shorts and flip flops.

If you’re going to a high-end neighborhood in Manhattan, check to see if there’s a dress code for the restaurant.

My point here is that where you live will dictate a certain type of vibe when it comes to apparel. Pay attention to it.

Conclusion:

Figuring out what to wear on a first date is the easy part. Now you’ve got to go on the first date! Realize that this may or may not be the man of your dreams. It might be the first of many first dates, and that’s okay.

You’re getting to know your single self at this point in your life, and the more practice you can get in, the faster you’ll know what you like and what you don’t.

Set yourself up for success on this first date. Keep your expectations low; at the very worst, you get to enjoy coffee, drinks, or dinner with a nice man. You might not have a love connection, but you might end up friends. So be open to where the date takes you!

And after your date, leave a comment below telling our Sexy Confidence community how it went…and what you wore!