What To Wear On A First Date

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what to wear on a first date

First dates, huh. They can be nerve-wracking because you can’t predict how they’ll turn out. But you know what else can make your palms sweat? 

What to wear on the first date. 

We only have one chance to make a first impression. A good first impression goes a long way. Whether your fashion sense is low-key or over the top, your first impression should represent who you are.

So, maybe you are undecided on what to wear to nail that first date? 

This article will give you tips, tricks, and hits and misses for your first date outfit.

Dress for you

Fitting a dress in front of a mirror
Fitting a dress in front of a mirror.

Dress to impress. Right?

No! Stop!

Dressing for yourself should be the main goal. Dress to suit your own comfort and style. 

Whatever you choose to wear on a first date, whether a pair of jeans with sneakers or a cute bodycon dress, comfort is key. It boosts confidence and makes you feel happy from the inside.

You ought to dress for you. It’s less about what you look like and more about how you feel about how you look. 

Outfit planning for a first date

Have you ever had a pile of clothes in your bed, yet you can’t seem to get the right outfit for your date? 

Yeah, we’ve all been there. Planning your outfits in advance is a life-changer.

Planning can make a huge difference because it can help:

  • Save time.
  • Reduce morning stress.
  • Eliminate outfit regret “I should have worn metallic shoes with this dress.”
  • Make you feel happy about your outfit choice.

Here’s what you need to consider when planning your outfit.

Figure out what the date entails

Whether you’re planning the date or the other person is, it’s essential to find out all the details about the date. Is it a dinner date? Ballroom dancing? Hiking? Then choose an outfit according to the event.

You have to know the time of the date. Is it during the afternoon or at night? The time of the date affects what you’re going to wear. 

When you are aware of all the activities, you can select the right outfit.

Go shopping

Choosing clothes in a shop
Choosing clothes in a shop.

This step is not always necessary, but it can come in handy, especially if you don’t have the right outfit for the planned activities or you feel the need to go the extra mile. Buying a new outfit can add excitement and fun.

However, new outfits can also add pressure because you’ve never experimented with them before. So, before you wear some new pieces, make sure you’ve tried and tested them in advance. 

Try different options

Have a few different outfit options. Try pairing different pieces together and see what works the best. You could ask a family member or friend to evaluate your options. 

Select the outfit you’re most comfortable in

The goal is to look stylish while being comfortable. 

Show off who you are

What you choose to wear on your first date should show off your style and flair. Your outfit can convey much about your personality, character, mood, and what you are as a person.

For instance, bold and bright colors show that you have a daring and exciting personality.

What should you wear to a first coffee date?

A first date at the coffee shop is supposed to be casual. So, dress casually but still look cute and put together.

A pair of jeans, a cute t-shirt or blouse, and sneakers are perfect for a coffee date. Also, a summer dress with a pair of sandals and a cute sling bag would be ideal for a summer look.
Keep it simple. Don’t go over the top with a sexy little dress and stripper heels, as you may not blend in with the crowd at the coffee spot. 

What should you wear on a first date for drinks?

Young couple on a romantic date drinking red wine
Young couple on a romantic date drinking red wine.

Going out for drinks can feel like less pressure. Summertime has the most outfit options. You can expose a little skin but still keep it cute and classy; an off-shoulder top and a skirt can be a great option.

Winter is about layering up. You should feel warm and cozy and still look cute. An oversized sweater with a pair of high-waist jeans and ankle boots is ideal.

What should you wear to an outdoor or picnic date?

Having fun together at a picnic
Having fun together at a picnic.

Do you know what else is important besides food, games, a bottle of wine, and a picnic blanket? wearing a comfortable dress. 

For an outdoor date, maxi dresses, midi-length knit dresses, and jumpsuits with wide-leg silhouettes can provide the ultimate comfort. 

Bright colors and fun patterns are perfect for outdoor dates.

What should you wear to a fancy restaurant on a first date?

Man in black and polka dot suit sitting on a chair inside a fancy restaurant
Man in black and polka dot suit sitting on a chair inside a fancy restaurant.

The first date to a fancy restaurant for either lunch or dinner requires you to dress up. Think work outfits but a little flirty. 

Jeans and tank tops can get messy. Instead, opt for midi dresses with a neutral-colored pair of strappy heels. Also, you can wear a top and skirt set for outfit coordination.

First raincoat must-haves for rainy days

Here are some essentials for a first date on a rainy day:

  • A raincoat
  • Trench coat
  • Block heel boots
  • Umbrella
  • Cute hat
  • A rain slicker for your handbag

What you should never wear on a first date

Woman removed her stilettos to wear a comfy shoes
Woman removed her stilettos to wear a pair of comfy shoes.

Remember, first dates make the first impression. And your outfits show off your personality. You want to avoid sending the wrong message by dressing in a way that’s too suggestive. You also don’t want to be too casual; it shows that you didn’t put in the effort.

If you want to see your date for the second time, avoid these fashion mistakes like the plague.

Super tight clothes

Super tight clothes can be especially uncomfortable if you’re going to have some food. They can make you self-conscious, which is distracting for both parties.

Loose clothes

Loose and baggy clothes show that you didn’t put in the effort to look great. They might tell your date that you’re not interested in yourself or the date. 

We said comfort is vital, and baggy may be comfortable for you. But that might be a recipe for a date ruiner. Wear something that fits right.

Super high heels

Those six-inch heels are ideal for a night out with your girls or maybe the fourth date. Super high heels can be uncomfortable because you might not feel or act natural. Instead, you’ll be focusing on walking carefully to avoid rolling your ankles.

So, spot your most comfortable shoes. It could be open sandals or two to three-inch heels.

Distracting clothes and jewelry

Avoid clothes that draw attention away from you—outfits with distracting prints and t-shirts with corny slogans and logos distract you.

Statement jewelry such as watches, bracelets, rings, and necklaces can add some personality to your outfit. But wearing all of them at once can overwhelm your outfit. Let one piece make the statement for you. 


It doesn’t matter what material they are made from or how expensive they are. Sweatpants should be worn at home when the only thing you plan on doing is Netflix and chilling. Sweatpants give the impression that you are lazy.

Is it okay to wear jeans on your first dress?

Yes, it’s okay to wear jeans, assuming that you’re comfortable and that the date takes place at a casual place. 

Is it okay to dress casually on your first date?

Couples having a coffee date
Couples having a coffee date.

If your first date is in a casual environment like a coffee shop or a local bar, casual wear is your best bet. Casual dresses or jeans with a classy top or blouse are all first date-worthy.

What do guys want a girl to wear on the first date?


  • Dress for the occasion
  • Show a little bit of skin; legs, collar bone, neckline.
  • Express your personality
  • Wear something you feel sexy in.

What do girls want a guy to wear on a first date?

According to research by The Essential Men, 101 women from different backgrounds were asked what men should wear on the first date. The results are as follows:

  • Effort (trying to look nice) is the most important quality of a man’s style on the first date.
  • Guys should wear the right fit. Not tight, not baggy, just the right fit.
  • Collared shirts show that you’re putting in more effort than plain t-shirts.
  • Nice pair of boots. Guys can wear them with a pair of jeans or dress pants.

Be authentic

Whatever you choose to wear, look like yourself. Showing up in a skater dress or suit for a first date is great, but only if that’s your typical style (depending on the activities).

The best impression you can make is an authentic one.

Final Thoughts

First dates can be very stressful. The least you can do to ease the nerves is to wear a comfortable outfit. Your outfit should express your personality and style.

Also, watch out for the first date deal breaker outfits. You might want to stay away from those on the first date.

Photo of author


Over the years, Stephanie has had her fair share of dating experiences. While some turned out great, others weren't so great. She believes that relationships are meant to be fun, exciting, and full of laughter. She wants to help men and women become confident, attractive, and successful in their romantic relationships.