What To Wear On A First Date + Date Night Outfit Ideas

Dating season is back! After this super weird year, I’m so excited to hear that everyone’s out there trying to find their soulmate. And no, I’m not being naive because if you just googled ‘what to wear on a first date’ and landed in this post, guess what? You care! And I love it. I’m so happy that you care because first dates are important and can be such a fun memory to look back at in a few years from now.

Me and my husband met on Tinder in September 2016 and our first date was on September 15th. 2 years later we got married on the same spot where we had our first date and to be extra annoying and corny, we also did it on the same date! But I share more on that below :)

First, let’s learn everything about what to wear on a first date!

In a hurry? Go straight to what you are looking for!

Our first date – What did I wear

Things to think about before choosing your outfit
Casual date night outfits – Styling tips
What to wear on a casual first date?
Perfect first date outfits (for dinner & drinks)
Dressy date night outfits with different jeans

Date night outfit ideas for Winter
Date night outfit ideas for Fall
Date night outfit ideas for Spring

Date night outfit ideas for Summer
Final thoughts
Related style posts you may also like

Estimated reading time: 32 minutes

Our first date – What did I wear

Our first date was so fun. It was a casual one since we decided to go to a place in Chicago called ‘Spin’ which is basically a ping pong bar. I cannot recommend doing something like this enough! We were both so nervous and hadn’t been on a date in forever, so having something to do during our date instead of awkwardly stare at each other definitely helped to break the ice.

It was tricky for me to decide what to wear because I wanted to look cute and showed that I cared, but I also wanted to be comfortable and beat him playing ping pong, so I wore a dress and sneakers. To be completely honest, I showed up in high heels but I packed my sneakers and changed into them when it was time to play ping pong after a round of drinks LOL. I still remember G’s face when he was coming back from picking up the rackets upstairs and saw that all the sudden I was 4 inches shorter. But hey, it all worked out for us. And I lost the ping pong match (but it was close!) that night in case you were wondering.

I’m going to give you a few casual first date outfit ideas that are both cute and comfortable, because first dates can be weird enough as they are, for you to wear uncomfortable shoes or things that are too tight on top of everything else.

Things to think about before choosing your first date outfit

Choosing what to wear on a first date it’s important, but you don’t have to overthink it either. Think about where you guys are going, the weather, if you will be walking, etc. If things go well after your date, you might go on a walk to keep talking and continue to get to know each other, so please, for the love of God, wear comfortable shoes!

Another thing I’m going to encourage you to think about, is how important it is to dress properly if you are looking for something long term and if you want to be taken seriously. Unfortunately, we live in a world where these things matter (way too much!) and the way we dress does say something about ourselves to the world. First impressions are everything and you can only have them once. That’s why none of the outfits I will share below are too revealing. First of all, it’s not my style and second, I think there are many ways to look sexy without showing too much or being too obvious.

This brand has really cute options and it’s sustainable too! Just keep in mind is a little bit expensive, but Jenni Kayne pieces are built to last you a lifetime!!

Perfect first date outfits – With outfit formulas

So, you are having the traditional first date; dinner and drinks. How cute! I’m honestly SO EXCITED for you! I wish I could relive my first date with my husband :)

It’s hard to pick which looks to share in here because there are SO MANY ways you can dress for a first date and it all depends on your style and what you feel comfortable in. However, these are so of my top picks for first date outfits and after a while, you can also recreate them for date nights with your loved one.

I’m sharing outfit formulas to guide you through creating your own version of these looks. In order to recreate them, take out each piece of the outfit formula (consider different options and take them all out of your closet). Mix and match some of the options together to see what works. Try things on if possible and take photos for later. This way you’ll have plenty of outfit ideas for next time you are going on a date.

Outfit formula #1: Comfy Pants + Cute top + Sandals + Accessories

Here you have 4 versions of this outfit formula. I bet you never considered wearing comfy pants for a first date. Well, you totally can! Just style them with a cute top, a crop top if the pants are high waisted, add neutral sandals or espadrilles and accessorize with a cute bag, necklace or statement earrings. All of these looks are comfortable and cute. And I know I always say this, but never underestimate the power of hair and makeup! Don’t dismiss any look until you’ve seen it after your hair and makeup are done.

I get 99% of my comfy pants from this store if you want to take a look. (they usually have great options from March to September)

This brand also has great options, it’s more affordable and bonus points for being sustainable!

Outfit formula #2: Skirt + T-shirt + Sandals + Accessories

Have you ever considered wearing a T-shirt for a first date? Or any date night? Let me tell you that you can totally pull it off! Pair it with a cute skirt and sandals and have fun with the accessories. Remember you can always layer a T-shirt with a long vest. Use any T-shirt you have; graphic, striped, neutral, printed, etc. Wear it with any skirt you have (as long as the colors/prints go together) and for the shoes, it can be sandals, lace-up shoes, heels or espadrilles. Here you have four different versions of the same outfit formula:

PS: If you need more outfit ideas with a white t-shirt, check out this post. And if you are interested in shopping for a T-shirt or any basic piece, this is where I get mine. (Use code WAYSOFSTYLE15 at check out for 15% off your entire order).

Outfit formula #3: Flirty dress + Sandals + Accessories

One of the easiest and most obvious ways to dress for date night, of course is with a dress and sandals. This is what I wear most of the times if we are going out at night. It can be as casual or as formal as you need it to be. It all depends on the occasion and what you feel comfortable in.

Dresses are great options for date nights and should be one of your first options when you are thinking about what to wear on a first date. They are too easy to style and you look put together in less than 5 minutes. There’s not much to think about when you are styling a cute dress. Here are some looks and different outfit ideas:

I’m almost certain I wore all of these looks for actual date nights with my husband. As you can see, you can play with the shoes and accessories and add an extra layer if you need to. You can pretty much wear any dress for date night if you style it properly and I hope these looks inspire you to create some outfits for yourself, adding your own personal touch and with dresses you already have in your closet! No need to go shopping all the time. Maximize what you already have :)

Date night outfits with jeans – Styling tips

There are many great ways to style jeans for a first date and for date nights in general. I have to admit that over time, after you keep dating the same person, it gets a lot easier to get dressed for date night. Even though I don’t wear jeans often, they are a closet staple and can easily get you out of trouble when you need to get dressed fast and you don’t know what to wear. Here are some things to remember when styling jeans:

You can never go wrong if you pair them with heels and a cute top (even a t-shirt & good accessories will work)
If you wear them with a T-shirt but want to dress it up a little bit, add a long vest, a statement jacket and cute earrings

Consider wearing a blazer too, but make it fun! Pair it with sexy heels, mix prints and add cute accessories. (if you have a white blazer, I created a blog post with all the tips on how to style them)

Here are some outfit options applying the styling tips above. These are great options to recreate if you don’t know what to wear on a first date:

Remember you can also create some looks with your black skinny jeans. You can dress them up or down in any way you want. It always works with a long cardigan and high heels (cozy and cute!). These are my favorite/sustainable long cardigans/sweaters. They will last you forever!!

Also read: how to wear a long cardigan

And last but not least, don’t forget about any other type of jeans you have in your closet! 3 out of these next 4 photos were taken on actual date nights. The are all very casual, but I think they are cute because of the accessories. As you can probably tell by now, I like to be comfortable when I go out on a date (and in life):

More date night outfits for every season

Ok, I’ve shared plenty of date night looks already, but I wanted to include even more date night outfits organized by season. It’s hard to get dressed when it’s cold outside. Trust me, I know this. I lived in Chicago for 7 years before we sold everything we owned and started living out of a suitcase, so I’ve had a fair share of Winter date nights. That’s why I decided to share more looks!

Cute date night outfits for Winter

Let’s be real. Winter is tough. It’s almost impossible to look cute and be warm simultaneously. Especially in Chicago. I usually wear tights or OTK boots during Winter date nights and try to add as many layers as possible. I mean that. Every time I wore any of these looks, I also wore my Winter coat over it. It’s not a big deal because you take it off anyways. I also don’t care too much about the shoes because we always took an Uber, so there was minimal walking. Here are some cute date night outfits for Winter with shorts, skirts and dresses:

Also read: How to style an oversized sweater

Date night looks for Fall

I have too many looks to share for Fall, so I’m going to organize them by pieces. Sometimes you may need tights, other times it’ll be that perfect Fall weather where you only need a sweater, but here are a few ideas to inspire you to create your own version of these looks.

Date night looks for Fall wearing skirts & shorts: Wear your shorts and skirts with tights and boots, pair them with cozy sweaters and add fun accessories!

First date outfit ideas for Fall with dresses: Don’t forget about your Spanx leggings (if you need a detailed review before you buy them, read this one), find ways to wear your OTK boots, take out your little black dresses and simply add an extra layer with a flirty jacket or even your denim jacket.

Classic first date outfits for Fall: These are super easy to recreate. Dress head to toe in black, add an extra layer and accessories and you will be good to go!

Cute date night outfits for Spring

Some of the looks I shared at the beginning can be for Spring too, but here are a few extra ones. It’s time to take out the pastels, sandals and of course, your denim jacket to create some cute Spring looks that are perfect for a first date:

Date night outfit ideas for Summer

Again, a lot of the looks I’ve shared so far can be perfect for Summer dates, but just in case you need more inspiration, here are some other ones. Some of these are a little bit dressier, but only because I changed the shoes and added a few accessories. I have been out on a date night with all of these looks and the hubby approves!

Casual date night outfits – With styling tips

What to wear on a casual first date?

How casual are we talking about here? I’m going to give you advice and styling tips based on what I think.

Casual first dates are great. I’m a huge fan. Ours went great as you probably know by now and I can’t recommend a casual first date enough! It’s already weird to meet with a stranger for the first time and you don’t always have a lot of things to talk about right away, so I encourage you to suggest a fun place to go to that includes an activity like playing ping pong, axe throwing, bowling, an escape room… I don’t know! Whatever sounds fun to you! Here are some outfit formulas and different outfit options for a casual first date:

Dresses + white sneakers:

Dresses and sneakers are a match made in heaven for casual first dates or casual dates in general. White sneakers look cool, pair great with almost any dress and you can complete the look with accessories like a hat, necklaces or statement earrings. Also, never underestimate the power of hair and make up. Some of these dresses may not look like ‘first date dresses’ at first, but after you see the whole look with the right accessories and hair and makeup, you’ll see that it works! (give me a chance here)

Don’t forget you can add a denim jacket or any extra layer like a long vest, lightweight trench or even tie something around your waist to accentuate it.

Also read: 70+ outfits with a jean jacket for every season

Any of these looks would work! It’s pretty much what I wore on our first date (I wish I had pictures of the exact look so I can show you). They are cute, comfortable and not super revealing, but you are still showing your legs. Pick any cute dress you have at home, pair it with sneakers and add some cute accessories. Don’t say no to the look until you’ve seen it with hair and makeup. Trust me, it makes all the difference!

PS: My favorite sustainable and affordable sneaker brand is called Cariuma. These shoes are insanely comfortable, one of the most sustainable and responsible brands out there and their prices range between $79 and $139. I have these white leather sneakers and I wear them ALL THE TIME! (I wrote a post on how to wear white sneakers and it has 60+ outfit ideas too if you want to check out more looks).

Other ways to wear white sneakers for a casual first date:

Sneakers with shorts:

Shorts are also a great option for date night. I love them during the Summer! Keep in mind when creating your own looks, that since you are already showing your legs with the shorts, don’t go too crazy with the top! Here are some examples that are different from each other, but they both work for a casual first date:

Casual date night look with shorts and sneakers

As you can see, I’m not wearing anything too revealing on top and I decided to wear shorts with details. Also, don’t forget to accessorize! A cute head scarf, headband or statement earrings can add a very special touch to any look.

Sneakers with skirts:

If dresses are not your thing, then try pairing your sneakers with a skirt. Notice I’m wearing a white T-shirt (more ways to style a white T-shirt here) in all of these looks, but you can’t tell unless you really pay attention! That’s why it’s so important to play with layers and learn to style really basic pieces to make them look different every time.

When creating your own looks with skirts + sneakers, think about how you can make it look more date appropriate, aka sexy without trying too hard. Notice I wore a leather skirt and a lace bralette in 2 of the looks because I wanted to add a little something extra ;) Try something like this with pieces you already have in your closet.

Sneakers with jeans:

I’m going to share more date night looks with jeans below, but if your first date is very casual and you want to wear jeans with sneakers, here are some ideas you can try to recreate. Add a cute jacket, or wear something sexier on top, pick the right jeans and have fun creating your own version of any these looks!

I shared more looks with white sneakers in this blog post. Some of these outfits are included in there, but I shared over 60 looks and more info about white sneakers in general, so make sure to check it out if you are interested.

But, let’s say sneakers are not your thing, I get it. Not everyone likes them and I know a lot of girls who would never ever wear sneakers on a first date! I hope you liked the other first date outfit looks I shared above! They are cute, snearkerless looks I think are also perfect for a first date. I shared the outfit formulas too, to help you think outside the box and create even more looks with things you already have in your closet. Don’t be afraid to get creative with what you already have :)

PS: we are currently traveling the world full time! ** If interested in checking out my updated travel outfits (right now we’re in Mexico!) check out this link!** (I just travel with a small suitcase and create many many cute looks!!)

Final thoughts

See? You can totally dress sexy without showing too much! I hope you feel inspired to recreate some of these looks with pieces you already have in your closet and that you have many ideas on what to wear for a first date. I shared over 70 looks for every occasion and season, but if you have any questions, don’t hesitate to reach out in the comments. I’m always here to help!

Good luck on your first date! I hope you figured out what to wear on a first date and I hope it goes well! If you are up for it, share in the comments what you are doing and what are you wearing. I love to hear stuff like that!

Thanks again so much for stopping by! Hope you have an amazing weekend :)

XO,

Aimara

What to wear on a first date – 70+ date night outfit ideas (for every season!)