• Home
  • Blog
    • Capsule Wardrobes
    • Personal Style
    • Sustainability
    • Lifestyle
    • Healthy Food
    • Reviews
  • Shop my Instagram
  • About
  • Say Hello
  • Follow
    • INSTAGRAM
    • FACEBOOK
    • PINTEREST
    • YOUTUBE
    • TWITTER

WAYS OF STYLE

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

in Lifestyle, Personal Style on 06/11/21

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!

  1. Our first date – What did I wear
  2. Things to think about before choosing your outfit
  3. Casual date night outfits – Styling tips
  4. What to wear on a casual first date?
    1. Dresses + white sneakers outfit ideas
    2. Shorts + white sneakers outfit ideas
    3. Skirts + white sneakers outfit ideas
    4. Jeans + white sneakers outfit ideas
  5. Perfect first date outfits (for dinner & drinks)
    1. With comfy pants
    2. With skirts
    3. With dresses
  6. Dressy date night outfits with different jeans
  7. Date night outfit ideas for Winter
  8. Date night outfit ideas for Fall
  9. Date night outfit ideas for Spring
  10. Date night outfit ideas for Summer
  11. Final thoughts
  12. 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!

cute date night outfit ideas
casual date night outfit
classy date night outfits
what to wear on a first date

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:

First date outfit ideas
What to wear for a first date

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:

What to wear on a first date
cute date night outfit ideas
perfect dress for date night
what to wear for a first date

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:

  1. You can never go wrong if you pair them with heels and a cute top (even a t-shirt & good accessories will work)
  2. 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
  3. 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:

Winter date night outfit ideas
winter date night outfit
first date winter outfit idea with sweater dress

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!
fall date night outfit
Fall date night outfit idea
  • 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.

casual date night outfit ideas
what to wear on a casual first date
casual date night outfit ideas

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

Did you learn what to wear on a first date today? Please pin it!

What to wear on a first date Pinterest Pin

Related style posts you may also like:

  • Why support sustainable brands? Your ethical clothing brand 2021 guide
  • Best ethical activewear brands for every budget
  • What is a minimalist wardrobe? Learn how to clean up your closet and which pieces you should keep
  • How to build a Summer capsule wardrobe
  • How to build your own capsule wardrobe for fall + outfit ideas
  • Outfit ideas for the Office
  • On the hunt for Spanx leggings? Read this Spanx Leggings Review first
  • 8 things you can do with a button down shirt
  • How to style pajamas as daywear – 7 looks with my PJ’s
  • How to style a white blazer – 10 stylish white blazer outfits

Share this:

  • Twitter
  • Facebook

Add a Comment

« How to wear a maxi skirt for every season – 10 looks to try out
How to style white jeans – Tips on how to wear white denim and create your own looks! »

Leave a Reply Cancel reply

Your email address will not be published. Required fields are marked *

About Aimara

Hi! I’m Aimara and I’m the voice behind Ways of Style.

I created this Blog as a space to express my thoughts and life experiences while wearing cute outfits of course! What started as a hobby is now my full time job and I’m here to encourage you to always be yourself, work hard and to always show up until your dreams come true. Read More…

More looks on Instagram!

I have a million photos to post! Trying to catch u I have a million photos to post! Trying to catch up here but somehow I never seem to sit down and share stuff in this account. I guess I like our travel account better! 😜 @waysoftheworld_ 

I’ve been trying to stay active with travel outfits and styling tips on the @shop.ltk app, so if you are interest you can check them all out by clicking the link in my bio. This dress was one of the best pieces I packed this time! It’s so cute for photos with any background basically!

We are currently on day 53 our of our 70 day trip through the Yucatan Peninsula 🤯 We’ve been to Cozumel, Punta Allen, Bacalar, Campeche, Merida and today we made it to Valladolid. We have one more stop before spending a week in Mexico City with family and then off to a new country we go! This lifestyle comes with its unexpected challenges, but we wouldn’t change it for anything!! 💕

Let this be a reminder to keep working hard to make your dreams happen! We are actively doing that right with @waysoftheworld_ 🙃 Hoping things end up working out for us!
…
#waysofstyle #campechemexico #travelblog #travelvlog #seetheworld #visitmexico #mexicotravel
What a crazy feeling when you start loving somethi What a crazy feeling when you start loving something you once thought was scary. It really makes you realize that fear is not real and exists only in your mind.

Never stop pursuing what sets your heart on fire. Even if it’s scary. And if you don’t know what that is yet, I encourage you to make the time to find out 💙

PS: this photo was taken on a scuba dive trip while in Cozumel a couple of weeks ago. If you ever find yourself there, do yourself a favor and do it with @scubatonycozumel 🤿 You will not regret it!

We are currently slow traveling through the Yucatan peninsula. We are having the time of our lives and documenting it all on @waysoftheworld_ 🌎 See you there? 🙃
…
#waysofstyle #scubadiving #experiencesoverthings #scubatony #scubatonycozumel #cozumel #cozumeldiving #cozumelscuba #fulltimetravel #travelvlog #travelblog
Yesterday we had a full day of exploring different Yesterday we had a full day of exploring different places and I needed different outfits but I didn’t have space to bring a whole new look. That’s when button down shirts + sneakers come handy! 

In the morning we went to the beach to snorkel and in the afternoon we explored Mayan ruins and had drinks and dinner. I needed sun protection and sneakers because they don’t recommend to walk the ruins in sandals (uneven terrain). I was able to change the wet bathing suit at the beach restaurant and didn’! get sunburn! Win win!!

PS: you can now shop all my looks via the @shop.ltk app ☺️ or via stories!
…
#waysofstyle #jumpsuit #howtostyleajumpsuit #grayson #buttondownshirt #cariumas #whitesneakers #travelstyle #vacationlooks #stylehack
🎅🏽 GIVEAWAY TIME!!!! 🎅🏽 Giveaway close 🎅🏽 GIVEAWAY TIME!!!! 🎅🏽 Giveaway closed! Winner @_downbythesea_ 

This little device has made a huge difference in how I travel! I barely have to worry about shaving thanks to laser hair removal 🙌🏻 And today, I’m teaming up with @silknsolution to give one away to one of YOU! 🌟

It’s super easy to enter:

1️⃣ FOLLOW me @waysofstyle & @silknsolution
2️⃣ LIKE this photo 
3️⃣ TAG a friend (each comment with a tag is a separate entry)
4️⃣ BONUS post this photo on your story and tag me! 

Winner will be announced this weekend!! Good luck everyone ❤️

Giveaway not associated with Instagram or Facebook. US or CAD residents only.
…
#silkn12daysofgiveaways #silknsolution #giftidea #hairremoval #mysilknsolution #silkn #giveaway #skincare #selfcare #selflove #treatyourself
Back home after spending the best 3 months of my l Back home after spending the best 3 months of my life in Turkey 🇹🇷❤️

We definitely left a piece of our hearts there, but we also learned so much and we know we will be back many times! And it feels good to be with family this time of the year.

I know I didn’t do a good job at posting in here. Honestly, I thought it was going to be easier, but starting a new Instagram, blog and YouTube channel from scratch for @waysoftheworld_ took a lot more time than I ever thought it would! So now, I’ll try to share some of my favorite photos from this trip in here because it’s never too late 🙃

This one was taken in a small mediterranean town called Kas. It was one of our favorite places in all of Turkey! It’s the perfect vacation spot to just enjoy life 💕

Feels good to be back! Hope everyone has a great week ahead and thanks so much for being here!!
…
#waysofstyle #travelstyle #kasturkey #vacationlooks #capsulewardrobe #experiencesoverthings #turkeytravel #visitturkey
Sharing 25 travel outfit ideas I created with the Sharing 25 travel outfit ideas I created with the best 7 pieces I packed! 🙌🏻

I believe these 7 pieces are not only good for traveling, but to add as part of your capsule wardrobe if you are thinking about starting to live with less things. I promise you won’t regret it!

I hope you find it useful and that you feel inspired to recreate any of these looks with pieces you already have in your closet. If you have any questions, let me know! I’m always here to help 🙂

Happy Monday ❤️
…
#waysofstyle #capsulewardrobe #whiteshirt #midiskirt #travelstyle #traveloutfits #capsulewardrobechecklist #capsulewardrobes #minimalism #sustainablefashion
Turkey has been incredible. We are blown away by h Turkey has been incredible. We are blown away by how beautiful it is, all the different landscapes, the food, and above everything, the people ❤️

Looking back to a few weeks ago when I was really afraid of going on this trip, thinking about all the things that could go wrong, being a little upset with myself in a way for not wanting the traditional life path I always thought was my only choice; get married, buy a house, have kids, save money and travel when you retire. That’s not for me. 

I’m very happy I followed my heart 💕 I wrote a letter to myself on the blog: “What’s the best that can happen if the worst happens?” You can check it out by clicking the link in my bio. I hope it inspires you to think about what YOU really want in your heart, make a plan and go after it (but be patient). I promise that if I did it, so can you.

You have everything it takes ❤️

Link in bio to read.
…
#waysofstyle #pamukkale #turkeytravel #followyourheart #seetheworld
I basically only wear olive green and white now 😂 

Our days in beautiful Kas are almost over. I’m leaving a piece of my heart in this cute little town and we will definitely be back! Now it’s time to hop on a 6 hour bus to Pamukkale and see what that place is all about! 

Honestly, the only reason we are going there is because of me. G is not too crazy about it, but I’ve seen it on Instagram so much that I wanted to see for myself what the buzz was all about. So I’ll keep you posted on what it actually is!

If you are interested in knowing more about Kas (and all the amazing places we are visiting) we share a lot more on @waysoftheworld_ 💞 
We talk about useful tips, costs, best things we do, where we stay and so much more. I also update those stories daily! So I hope to see you there 🙃

Until next time friends 👋🏻
…
#waysofstyle #travelstyle #midiskirt #traveloutfits #kas #kasturkey #worldtraveler #styleblogger #styleinspo #mystyle #fashionblogger #capsulewardrobe
I was brave 💙 This was the most amazing experi I was brave 💙

This was the most amazing experience. I was SO nervous and anxious before but somehow I managed to push through and tried this very scary thing for the first time. And you know what I learned? That I loved it! I would do it again a million times! It wasn’t scary at all. It was all in my head and it wasn’t real. Also, they had the sweetest dog at the shop named Lucy that really help me not to think about it (swipe to see her 😍)

We didn’t do any crazy tricks like G did and it was a very peaceful flight. It’s up to you how you want to do it.

I can see why Ölüdeniz is one of the top places in the world to go paragliding. If you only want to do it once to cross it off your bucket list, this is the place you go to. We shared a post about with useful information in case you are interested. Link in bio + stories.

Would you do it? 🙃
Make sure to follow our adventures around Turkey on @waysoftheworld_ 🙏🏻
…
#waysofstyle #paragliding #oludeniz #exploreturkey #turkeytravel #bebrave #experiencesoverthings
Follow!

BLOG CATEGORIES

  • Capsule Wardrobes (5)
  • Healthy Food (11)
  • Lifestyle (25)
  • Personal Style (34)
  • Reviews (9)
  • Sustainability (7)
  • Travel Style (4)

Copyright © 2023 · glam theme by Restored 316

Copyright © 2023 · Glam Theme on Genesis Framework · WordPress · Log in