What To Wear On A First Date (53 Stylish Ideas)

Last updated on June 17, 2022 by April Maccario

First dates can be scary and the thought of the date can be stressful enough before you even start to think about what you should choose. 

You are likely already worrying about how the date is going to go, how you will manage any awkward silences, and whether you will have enough to talk about with one another. Choosing the right outfit can help you to feel more confident. 

Even if this doesn’t work out these tips on what to wear on the first date can help you in your everyday life as well as on any other dates that you go on in the future. They will give you the confidence to go out without worrying about what they may think. Remember the most important thing about dressing for dating is what you want to wear.

Even if you really like someone and you want to make a good impression, it is important to remember to never change your style or tone yourself down for anyone. If you love to wear statement outfits, then wear them without worrying about what other people or your date may think of you, wear whatever makes you happy not what you think other people will like. 

Tips And Ideas For Your First Date Outfit

First dates can be daunting, especially if it is with someone that you already like and you want to make sure that things will go well. 

There are some things that you can do to make things go easy and make yourself feel more relaxed and comfortable. Picking the right outfit can go a long way in removing the stress of a first meeting-- choose something that you feel good in. 

Picking an outfit that you feel good in is so important, there is no point in wearing something that you don’t feel comfortable in. If you choose something that you think your evening will like but it just doesn’t make you feel good about yourself, you are going to spend the whole night worrying about how you look and about how uncomfortable you feel. 

Rather pick something that you feel amazing in and bring out the best version of you. If you never wear dresses in your everyday life, now is not the time to try one. Pick something that you feel completely comfortable and confident in and your partner will notice the best version of you, rather than someone that is worried about how they look. 

Outfit Ideas

Choosing first meeting outfits can be one of the most daunting things about dating, however, it doesn’t have to be. You likely want to make a good impression and are worrying about whether he will like your outfit or not. However, one of the most important things to remember is that you choose an outfit that makes you feel good rather than what you think someone else may like. 

Outfit Ideas

One of the biggest mistakes that many people make when they are choosing their dating outfits is that they choose something that they think will create a good impression, but they fail to think about what they really feel comfortable in themselves. Rather than trying to pick something that your partner will like, pick something that makes you feel the best version of you. 

It can also be helpful to think of the venue of the occasion if you are going for a casual coffee a simple dress layered with a cardigan could be the perfect option. However, if you are going to a fancy bar, it may be a good idea to find your favorite skirt and heels. But if you don’t love wearing dresses, wear your favorite jeans instead!

Here are some tips when picking your outfit!

  1. Add a statement piece of jewelry for a formal occasion 
  2. Choose a fun piece of jewelry to start the conversation
  3. Don’t pick something that you know you cannot walk in
  4. Don’t pick something that you are not comfortable in
  5. Remember to pick something that makes you feel good
  6. Be confident in what you are wearing
  7. Consider a cute skirt or jeans and a top, whatever makes you feel confident
  8. Pick your favorite pair of jeans and a top for something simple
  9. Don’t try to hide your style
  10. Choose heels if they are something you feel comfortable in them
  11. Choose converse or trainers if they make you feel happy
  12. A black dress can never go wrong
  13. Consider the event before you pick your clothes
  14. Decide whether you want to dress formally or casually
  15. Wear something that makes you feel relaxed, whether that is a skirt or jeans
  16. If you are going on your meeting straight after work, pick a skirt that is easy to put on
  17. Choose a nice bag as a statement piece
  18. Add some red lipstick if you are looking for a transition from your work clothes
  19. Be confident in the clothing that you choose
  20. Wear what makes you feel good about yourself
  21. Don’t choose a dress or clothes that make you feel uncomfortable
  22. Choose an outfit that makes you feel like the best version of you
  23. Don’t worry too much about rules, just wear what feels right for you
  24. Wear something freshly washed, to avoid stains
  25. Pick clothes that fit you well and make you look put together

Picking The Right Outfit

There are some things to remember when choosing your clothes, first, think of the venue of the occasion and dress accordingly.

If you are going to a casual cafe, pick a more relaxed outfit, if you are going to a fancy restaurant, you may want to pick something a bit more dressy. But remember, there is no need to stress too much about what you are going to wear. 

Picking The Right Outfit
  1. Put some thought into it, but don’t stress too much either
  2. Don’t spend all of your time worrying about what to wear
  3. Don’t pick an overly ambitious outfit 
  4. Stick to a neutral palette to avoid any mishaps
  5. Choose a simple skirt, jeans, and a top if you are not sure what to choose
  6. Pair white with red lipstick for something fun and flirty
  7. Show off your favorite body part
  8. Pick a maxi dress for something that is comfortable yet beautiful and perfect for an evening
  9. Consider whether you are going to a chilled pub or a fancy bar and dress accordingly
  10. Choose a first date outfit that puts you at ease
  11. Don’t choose something that makes you appear high maintenance
  12. Keep your hair simple too
  13. Avoid wearing too much makeup, especially if this is not something you would usually do every day. 
  14. Find a balance between making an effort and overdoing it
  15. Don’t choose an outfit that is too tight or restricting
  16. If you are going on a date straight from work, consider a shirt dress and a pretty shoe
  17. Choose something classic if you want to dress up your usual jeans - pick a pretty top and mom jeans with a low heeled shoe
  18. Pick a patterned skirt, a simple t-shirt, and flat shoes for a relaxed but fun outfit
  19. If you want something comfortable but flirty and exciting at the same time, pick a fancy top and pair it with high waist jeans and low heels
  20. For those looking for a relaxed but cute option for a first date consider a flowy dress paired with trainers for the perfect comfortable but pretty outfit
  21. Choose denim shorts and pair them with a pretty top and statement shoes for an easy but chic outfit that is perfect for a summer evening
  22. If you want to make a statement pick a bold top and pair it with a printed skirt and trainers. Don’t tone yourself down and wear what you want
  23. If you are excited for a fun evening, pick a printed skirt and pair it with a pair of chunky boots
  24. If you are going for a relaxed coffee date consider wearing boyfriend jeans and a cardigan for a cozy and comfortable look
  25. For a perfectly relaxed look go for an oversized t-shirt and a blazer, paired with boots and statement accessories
  26. If you are going for drinks in the evening pick a leather jacket, jeans, and heels
  27. A satin midi dress is a perfect option for a date night outfit, pair it with statement earrings and sandals
  28. Remember the most important thing when planning your date-night outfit-- pick whatever you want and don’t tone down your style for anyone!


What should a woman wear on a first date?

When going on a first date it is important to remember to pick something that you feel comfortable and good in. There is no point in dressing in a way that you think other people may like but you don’t feel comfortable in. Don’t alter your style for anybody and choose that statement dress that you love even if you think that your date may not love it. 

What should you not wear on a first date?

When going on a first date and picking clothes for it remember to avoid anything for the date outfit that makes you feel uncomfortable. Pick something that you love and makes you feel like the best version of yourself rather than something that you think a first date outfit should look like. Show the true and most authentic version of you through your outfit too. 

What is the best color to wear on a first date?

There is no right or wrong color to choose for your first date outfits, instead, think of a color that makes you feel good and confident about yourself. If you are going somewhere relaxed and want a chilled outfit go for a black dress or neutrals. However, if you are going out and you want to make a statement choose your favorite brightly colored dress. 

What should I wear on a first date in 2020?

There are no set rules as to what you should choose as your outfit for an evening, however, remember to choose something that makes you feel happy. There is no point in wearing a dress if you never wear dresses normally and you never feel comfortable in them. Pick something that you feel happy and comfortable in and you will feel a lot more confident in yourself

Is it OK to wear jeans on a first date?

When choosing date outfits it is important to remember what you love and what you would wear on an everyday basis. There is no point in wearing something that you don’t feel comfortable in. There is absolutely nothing wrong with wearing jeans on a date, especially if you are going on a coffee date or you are meeting him at a relaxed bar. 

To Sum Up…

Going on a first date can be daunting but choosing your outfit for a date night can be one thing that makes you feel more confident and less stressed. By picking something that you feel comfortable and confident in when choosing first date outfits, you will likely enjoy a much more successful date and your date will see the true and most authentic version of you. 


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Do you hate it how everything seems to always revolve round him while you just seem to be an afterthought sometimes?
We hear this all the time from women that contact us asking for help with their relationship.

The thing is that which causes men to behave this way is actually something how men are wired. Once you understand how this works, it's relatively easy to change with a few subtle things you can say to him today.

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April Maccario
I'm a huge nerd when it comes to understanding how relationships between men and women work, and what drives a certain behavior. I spend much of my time getting into the nitty-gritty and try to share my findings on this site with the hope of making life a little easier for women that are struggling in their relationships or love life.

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