What You Should Wear And Not Wear On a First Date

While talking to a friend of mine on the phone earlier today, I heard a lot about what they were going to wear on their first date. Realizing that this might be a more common issue than I might have thought, I decided to do some research to help others out who are dealing with the same problem.

What should you wear and not wear on a first date? The outfit that you wear on a first date will really depend on what makes you feel comfortable. There is no right or wrong answer to this question, it is merely based on preference and what will give you the confidence that you need to get through it.

You should not wear anything that makes you feel self-conscious about your features, and you shouldn’t put something together just because you think it will impress the other person. When in doubt, just be yourself.

When it comes to going on a first date with someone that you really like, it can be hard to decide what you will be wearing. In hopes of impressing them, you might be running around in circles in the coming hours with no idea what you should put together.

In this article, we will be offering a little bit of guidance in this aspect. So, if you are stressing about what to wear on a first date, you don’t have to look any further. Keep reading to find out everything you need to know about the topic from point A to point Z.

What Should You Wear On a First Date?

Whether you are currently on the dating scene or you were previously, we all know the feeling that comes with finally getting that first date with someone that we are interested in. Both men and women can relate to the butterflies that come with making that first connection and agreeing to spend more time together.

On the days leading up to your date, you are probably scrambling around and thinking about what you are going to wear. First dates are essentially the first impression of really getting to know someone.So, as a result, you will need to look the part in order to get anywhere.

After all, no one wants to go on a date with someone who doesn’t put forth the effort to make themselves look good, and they definitely won’t take you seriously if you don’t.

In this section, we will be talking about everything that you need to know about what you should wear on a first date. In the list down below, you will find a list of things that need to be addressed while you are in the process of selecting your outfit.

Here are some factors to consider when you are deciding what to wear on your first date:

  • Where will you be going on the date?
  • What will the weather be like?
  • What will you be doing for most of the time?
  • How long do you expect the date to last?
  • What type or style of clothing makes you feel most comfortable?

First of all, you will need to think about where you will be going on the date. Unless it is some kind of surprise, you probably already know where you are going. And if not, your date has most likely given you some kind of heads up about whether the date is going to be formal or more on the casual side.

Are you going to sit down at a five star restaurant for dinner? Or, are you going to take a nice walk through the park and maybe stop in at a sports bar for a few drinks?

The place that you are going will really have a big effect on what kind of outfit you will wear. You wouldn’t want to wear a dress to a park, or show up to an upscale location in a baseball cap and sneakers.

Along with considering where you will be for the date, it is important to check the weather for that particular day or night. Will it be hot and sunny or cold and rainy?

Knowing this information will help you to further plan your outfit so that you will not be regretful during the date about what you put together beforehand. If you know there is a good chance of rain, you can come prepared with a jacket and umbrella.

On the other hand, if it is going to be hot and you plan to be outside for most of the date, you should wear something light and breathable.

In addition, you will also need to think about what you will actually be doing on the date. There are a lot of ways that this could go, depending on what was decided or agreed upon when the initial date was planned.

When you are going on a date, you can be in a formal setting where you are sitting down for the entire time, or you could be doing something active where you are running around or playing a sport together. Either way, you need to be realistic about what types of movements or positions you will have to be in to decide on what type of outfit you will need to choose.

For instance, if you are going out to dinner, you might not want to wear a tight shirt that will show the areas of your stomach that are not so flattering. In this case, you might choose to go a little bigger on the top and more fitted on the bottom.

On the contrary, if you are playing paintball, you should wear something that you can easily bend down, run around, and even jump in. Going on a first date is not always just about looking good, you should feel good as well.

So, if something is going to limit the movements that you need to make during the duration of your date, you will have to cross it out.

Next, think about how long you expect the date to last. If you are going to be outside for several hours of the day, you might need to think about how your outfit will hold up.

For example, you might choose to wear a bright white t-shirt on an outdoor date where you are walking through a park in the sun. However, if you plan to be there for a long period of time, you could start to sweat and it could be very noticeable.

In this situation, you could choose a more loose shirt or something that is a darker color so that these kinds of things would not be as visible.

On the other hand, if you are going to get a quick drink at a bar, you might be able to get away with wearing something that is a little bit less comfortable, since you might only be there for about an hour.

Finally, you should consider what type or style of clothing makes you feel comfortable. No matter what the setting of the date is, you should stick to being yourself and putting together something that gives you confidence. At the end of the day, the date won’t go very well if you feel self-conscious and awkward about the way that you look.

The main points to take away from this conversation are to think about yourself being on the actual date and deciding how you will get the best results, along with what makes you feel comfortable in general.

So, now that you have probably gone through all of these questions in your head and came up with a general idea of what kind of outfit you might want to put together, you can go through a few additional guidelines to help you make the final decision.

Whether you have a few options in front of you or it is just a thought at the moment, you can find some more critical questions in the list down below.

Here are some factors to consider when you are making the final decision on what to wear for your first date:

  • Does this outfit make you feel comfortable?
  • Does this outfit compliment all of your good features and hide your bad ones?
  • Will you be able to wear this outfit for the entire duration of your date?

When you are trying on the potential first date outfit, you should ask yourself if you feel comfortable in it. In other words, when you are looking at yourself in the mirror and the camera at all angles, do you think that you look good?

Furthermore, will this outfit give you confidence while you are speaking to your date? The clothing that you choose should take the stress off of focusing on your looks, and help you to really enjoy your date instead.

As humans, we all have some features that we like about ourselves, while others seem to be a little bit less flattering. Does the outfit that you chose compliment all of your good features, and hide the bad ones?

You can also check out our article on 10 killer trends for fashion for even more ideas on what you can wear!

Finally, will you be able to wear this outfit for the duration of your date? As previously mentioned, comfort is key in these situations. You always want to be able to sit or move around for the entire duration of your date without being uncomfortable.

What Should You NOT Wear On a First Date?

Now that we have gone over a pretty detailed outline of what you should wear on a first date, you might be wondering if there are some things that you can try to avoid as well.

While you can go through all of the steps and check the boxes that were previously discussed, you might run into a few questionable areas during your process of finding that perfect first date outfit.

In this section, we will be talking about some things that you should avoid when you are in the middle of making your final choice. Take a look at the list down below to get a general outline, and keep reading to get all of the details.

Here are some things to avoid when you are putting together your first date outfit:

  • Clothing that does not fit properly
  • Clothing that limits movement or comfortable sitting
  • Colors that make you feel self-conscious
  • Pieces that highlight your least favorite features
  • Sacrificing comfort to impress your date

The first thing to stay away from is clothing that does not fit properly. If something is too tight, it can really stop you from moving around. If it is too big, you might worry about how your shape and figure looks.

When in doubt about what you will be doing on your date, pick something that is comfortable for moving around and sitting.

In addition, you should avoid colors that make you feel self-conscious. Whatever your favorite color is, you should stick with. Don’t pick something that highlights your least desirable features.

Finally, you should never sacrifice your own comfort just to impress your date, due to the fact that you think they might like something. All in all, your date is already interested in you, so come the way that you are!

What Should Men Wear On a First Date?

While it is true that women usually spend a lot of time putting together outfits and finding what looks good, first date outfits for men is a topic that is rarely discussed. In fact, you can probably find 10 online resources for women’s outfits before you find one of them for men.

In order to help you out with this concept if you happen to be stuck in your decision making process, I have put together one final list that will give you some suggestions for a great first date outfit.

Here are some suggestions for a great first date outfit:

  • Stay away from hats
  • Don’t dress too casual (unless the date is casual)
  • Iron or dry clean your clothing beforehand
  • Accessorize your outfit with a watch
  • Try a nice shoulder bag or briefcase

Whether your date is formal or casual, it is a good idea to stay away from hats in general. This is due to the fact that a hat will hide your face, and make the conversation a little less intimate.

Hats also have the tendency to make something look way less formal, and you could give your date the wrong idea about how important the outing is to you.

With that being said, don’t dress too casual either, unless the date is casual. Iron or dry clean your clothing before the day of, so that you won’t look like you rolled out of bed and showed up.

Men can do well with accessories, too. Try wearing a nice watch on your wrist to add a little extra to your outfit. You can also bring a shoulder bag or briefcase for a professional and mysterious look.

To conclude, choosing an outfit for a first date can seem like a very intimidating task. However, with the use of all of the helpful tips that were outlined in this article, you will be on your way to putting together the perfect outfit that both of you will love.

The most important thing to take away from this information is to always be yourself, and dress however makes you comfortable, no matter who you are trying to impress.