One of the hardest things about dating is trying to figure out how to dress for a first date. After all, first impressions really do matter. And when you’re looking for love (or just someone to spend time with this season), that can feel like a lot of pressure.

But there are some simple tips on how to dress for a first date that will make choosing your perfect outfit way easier.

How To Dress For A First Date

1. Be Yourself

The whole point of a first date is to get to know someone. And to let them get to know you. To do that, you need to be yourself, even in your style. Don’t wear something just because it’s fashionable, wear something that expresses who you are.

Of course, you need to put in some effort. So, leave the sweats at home but make sure your outfit feels like “you.”

2. Dress For The Venue

Showing up to a coffee date wearing a cocktail dress is weird. So is wearing a pair of jeans at a fancy dinner, or a pair of high heels on an outdoor hike.

Make sure to think about that when you choose what to wear. Your outfit should fit the venue and the weather.

3. Emphasize One Key Asset

Sometimes a short, skintight dress with a lot of cleavage is a fun look. But that time is generally not on a first date. There’s such a thing as “too sexy,” especially when you’re still in the early stages of a courtship.

Besides, you can actually look sexier if you’re not trying so hard to look sexy. So, choose one key asset to highlight. If you’ve got great legs, for instance, wear a skirt with a loose top. Or a short dress with long sleeves.

4. Choose The Best Colors

When you’re thinking of how to dress for a first date, make sure to consider color. Everyone has a go-to color that looks great on them. As long as that color is season and venue appropriate, try to incorporate it into your outfit.

If you’re stuck, red or black generally work well.

Another tip: wear solid colors. You don’t necessarily need to go monochromatic, but wearing solid colors instead of multiple prints or patterns is going to be more flattering.

5. Go Timeless Over Trendy

First dates aren’t the place for daring fashion choices. Even if being super trendy is you, it can make you seem unapproachable. It’s best to wear something chic and timeless.

There’s a reason the little-black-dress is always in style!

6. Stick To Simple Jewelry

Chunky necklaces and layered strands might be in right now, but again, it’s not a great first-date look. Too much jewelry can be distracting. Instead, wear simple, elegant pieces and do it in moderation.

If you love rings, go ahead and wear a few, but in that case, leave the bracelets at home. Same with earrings or a necklace; if you want to wear a statement necklace, go for it. Just make sure to keep your earrings simple.

7. Keep Your Makeup Minimal

Just like with jewelry, wearing a lot of makeup on a first date can be distracting.

It can also make you seem insecure or shallow. Instead, keep your makeup natural and minimal. No need for a dramatic cat-eye or a ton of contouring.

And just like with your outfit, emphasize one key asset like your lips or your eyes.

8. Wear What Feels Good

This goes for both internal and external comfort. For example, you shouldn’t wear sky-high heels on a first date; a twisted ankle isn’t a good look on anyone.

At the same time, if you show up in yoga pants and an old-tee, you might be physically comfortable but chances are you’re not going to feel incredibly sexy. Instead, wear something that makes you feel confident and put-together but also comfortable and able to relax. That way, you’ll make the best first impression possible.

First Date Outfit Ideas

1. Jeans are a Classic

Wearing a good pair of jeans is always a safe bet.

Plus, you can easily dress it up or down. I personally love wearing wedge heels or ankle boots with a pair of jeans.

You could also try a crop top or a sleeveless blouse, especially if you’re wearing a more relaxed pair of jeans. For skinny jeans, you can try an oversized sweater or an off-the-shoulder shirt.

2. Try A Wrap Dress

A casual dress is one of my favorite first date outfit ideas. It shows you’ve made an effort, but it’s not over the top.

And wrap-dresses have a way of emphasizing your figure without looking like you’re trying too hard.

Pair it with simple sandals or wedges for a timeless look. Or, you can also make it edgier with a leather jacket.

3. Mix and Match

This goes back to the whole “emphasize one asset” concept. So, if you’re wearing a short skirt or tight jeans, wear a loose top to balance it out. You can also pair a dress with sneakers, or jeans with heels.

Do you have any other tips on how to dress for a first date? Let me know in the comments below!



  1. avatar
    Flattery says:

    When I saw the illustration for this article with the butt cleavage dress I nearly fell over laughing. Brilliant.

  2. avatar
    mindbeautysimplicity says:

    agreed! jeans are such a classic for a date night [ especially first dates ]. great reminders here for those going on first dates. thanks for sharing, katie!

    1. avatar

      Thanks so much! glad you enjoyed!

  3. avatar

    I love these tips for a first date! I will always dress in a way that reflects me and emphasise my best features! x

    Lucy |

    1. avatar

      Always a great plan!

  4. avatar
    According to Chren says:

    Your advice is spot on for first dates. great outfit choices. We agree that looking natural and chic is important.

    1. avatar

      I think neutral clothing choices tend to look good on everyone!

  5. avatar

    I like your tips! No.5 is the best for me. Timeless is always better than trendy. Thank you for sharing.

    1. avatar

      Absolutely agree! Thanks for reading

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About Author

30ish Lifestyle blogger, relationship "expert," and modern-day agony aunt.
Sometimes humorous, always honest.