Okay, so for every reddit forum asking for advice about date style, there are just as many idea articles about this topic. Well, I decided to hop onto the gravy train since I had two cents to contribute. I even put together a Youtube video to show you how my clothes hunting process looks like! Naturally you want to impress your date, and it’s totally normal for your mind to jam in this scrupulous effort to look just right. Trust me, I’ve been there. In the heat of the excitement, I tried on some clothes that I thought look absolutely put together at the time, but now I look back and think to myself, “What was the matter with me?!”

Well! Now that it makes the two of us, I have scoured the Net and Pinterest and boiled down some common trends for different date locations plus my trademark timeless style. And afterwards, read on for further suggestions for second and third date outfit ideas in case you’re feeling lucky!

First date

If you’re meeting in a cafe…comfortable/effortless.

  • leather blazer + turtleneck + trousers + vans


  • wrap coat + hoodie + jeans+ ankle boots

The emphasis here is on comfort, soft clothing and daily wear since you’re meeting someone in an everyday setting.

If you’re meeting in a museum…casual chic.

  • Raincoat + jeans + Canvas sneakers


  • blazer + shirt + scarf + bootcut jeans + canvas sneakers

If you’re heading to a museum, which people visit less often — unless you’re like my last date who goes to art museums every weekend without a miss! — then you might want to put a little more emphasis into sophisticated pieces.

I especially recommend low-block heels à la French ladies’ style as I find them very dressy but still comfortable enough to walk around museums for hours.

If you’re meeting at the movie theater…flirty

dress + bangles + kitten heels/oxfords


oversized coat + miniskirt + flats

Why not? Movie theaters to me signal a conventional but sweet romance that I think might amp up the romance — and that talk about expectations for each other.

If you’re having a dinner date…elevated/romantic

BLD + strappy heels


off shoulder + fur coat

It’s dressy without going overboard. Incidentally it’s also good evening wear! Usually when I think of dinner dates, I imagine a lot take place near the evenings.

What To Wear On the Second Date

Alright, so let’s say you slayed your first date — Woo-hoo! Now you’re at crossroads: what about the second date? How come we don’t talk about that one enough?

It might look a little complicated. After all, you want to make an impression, but you don’t want to go all out just yet!

My friends, here’s my suggestion: stick to your style.

That’s right. For instance, you’re more into minimalist casual and you hate all the extra fuss, then that’s your go-to for your next look.

If you’re more into flouncy, flirty skirts like I am, then stick to that palette and let your guy know that you are cute and bubbly at heart.

Of course, since everyone has their own individual style, it’s more nuanced than that. But just remember, what’s the point of the second date? It’s to show your true colors without being too forwards. It’s to show that you’re open to exploring the relationship without being too hasty.

What to Wear on the Third Date

Now’s your time to go crazy! …okay, not too crazy. But if you’re in your third date, you’re probably smitten by now. For that, you might want to display your more romantic side in appreciation for him. Don’t be afraid to look your best for this one! I think as is popular on Instagram, you can see a lot of flowers paired with your outfit.

Here are some ideas:

  • Red lipstick. I recommend matts since they stay on well, especially if you want to go in for a kiss without smudging the poor bloke’s face!
  • Sheer black tights for allure.
  • Pussybow/ruffle blouses.
  • Full-length skirts. Probably pink or pastel.
  • Pastels.
  • A slit skirt.

Personally I would go for the boatneck lace top and miniskirt that I got from yesstyle that’s currently in my closet! If it goes out of stock, try a similar-looking alternative.

How well do you relate to my style mood boards? How long would you wait until you lean in for the kiss (lipstick or not)? I’m genuinely curious about the last question! Thanks for reading!