How To Dress In Your 20s For Your First Date

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September 9, 2019

Dating, Social

Dr. R. Y. Langham

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When you go on a first date you want to make a great impression, otherwise, you wouldn’t go on it. However, trying to decide how to dress in your 20s for a first date can be just as stressful as trying to decide where to go. You want to show off your best assets, but what is considered showing off too much or too little? It’s kind of confusing, especially if you don’t know your date that well and/or your date destination is a “surprise” or unfamiliar.

So…many…options…

Should you dress comfortably? Should you dress up? Should you wear jeans, shorts, a skirt, a t-shirt, a blouse, a short dress, a long dress, or khakis? Should you dress for warm weather or cold? Should you show a little cleavage or no cleavage? So many options!

Pick your favorite outfit

Well, my suggestion is that you select an attire that makes you feel beautiful/handsome, sexy, confident, joyful, and comfortable. Impossible feat? Not really. The thing is if you feel confident and attractive, you’ll shine during your date.

You’ve got this! Now, go have some fun!

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Actionable Steps

Read the longer version

You can learn more about how to dress on a first date by reading the following articles, reviewed to be the best by our professionals: What to Wear on a First Date? We Asked the Experts! by The Every Girl, How to Dress to Impress on a First Date by WikiHow, 11 Style Mistakes To Avoid On A First Date by Bustle, and What To Wear On A First Date? What Not To Wear? by Style Craze.

Don’t take everyone’s advice on how to dress in your 20s

Don’t take everyone’s advice on how to dress in your 20s, especially for a first date. In other words, be careful who you listen to. Only take advice that actually works for you. A fun way to decide what you’re going to wear on your first date is to stage an impromptu and “unofficial” fashion show for a few of your buddies.

Ask for their honest opinions on your selections – and listen to them with objective ears. Now, you don’t have to take the advice if you don’t feel it works for you, however, your buddies deserve to be listened to at the very minimum. I mean, they took time out of their days just to help you plan for your date, so you owe them that.

Your friends are your best supporters and your most honest critics. They want you to look your best and dazzle your date, so it may be worth really taking into consideration what they have to say about how to dress in your 20s for a first date.

Dress appropriately for the occasion

In other words, try to avoid “over-dressing” or “under-dressing” for the activity – if possible. I realize you may not know exactly where you are going for your first date or the location may be unfamiliar to you. In the first case, there’s probably nothing you can do about it – unless your date drops some hints in front of you, but in the second case, research the location to determine what you should wear. Websites like Yelp and Trip Advisor can provide you with honest reviews and real pictures of the venue, restaurant, or location.

You can also find information on the location’s website. Knowing how to dress in your 20s is imperative to having an awesome first date. If you’re not dressed appropriately for it, it will cause you to feel uncomfortable and self-conscious, ultimately putting a damper on the date. For instance, if you and your date plan to go to a concert for the first date, you’ll probably need to put on a pair of jeans and a nice or cute t-shirt.

You don’t need to wear a suit and tie or an elegant black dress to the event, because it’s low-key. If you show up looking like you’re about to go to a fancy dinner, you’ll be way “over-dressed.” And, on the flip side, if you show up in shorts, a tank top, and flip-flops to a fancy dinner, you’ll be way “under-dressed.” Understand that clothes send a message, so make sure you’re sending the right one on your first date by knowing how to dress in your 20s for the right event.

There are plenty of websites that can provide you with fashion tips for different types of dates. Therefore, you should never be “over-dressed” or “under-dressed” for a date – unless you don’t know where you are going. If that is the case, chalk it up to being uninformed – by your date – not from being careless.

Wear a color that compliments you

You’ll also want to wear a color that actually complements your skin tone. You’ll need to know what color looks good on you. Understand that the color that makes you dazzle may not be your favorite color. So, in this situation, go with what complements your skin tone. If you can’t tell if a color looks good on you, ask someone you trust to give you the “real deal.”

Wearing colors that flatter you can help your date remember you more vividly. You’d be surprised how memorable a first date outfit can be many decades later. So wow your date with complementary colors.

Dial down the perfume or cologne

For your first date, you may want to dial down your perfume or cologne a notch or two. Less is more in this case. You don’t want to suffocate or nauseate your date with an overpowering fragrance, do you? So, stick to subtle, but enticing scents to make a memorable first impression.

Don’t be too “trendy”

Try to avoid being too “trendy” during your first date. I get that you want your date to view you as stylish, but some of the newest “trendy” styles are just too “trendy” for a first date. So, hold off from showcasing a Tom Ford lookalike piece – until you get to know each other better. Instead stick to the “basics” – i.e. a cute black dress with low pumps and cute jewelry or khakis with a Polo or button-down dress shirt, a nice wristwatch, and causal loafers.

A first date is not the time to “experiment” with the newest trends. Stick to clothes that fit your body and compliment your shape and skin tone. There will be plenty of time to wow your date in the future with your unique style and the “hottest” clothes.

Pay attention to your shoes

Lastly, it is important that you pay attention to your shoes. Ladies, do not wear shoes you have never worn before. And, do not wear stilettos on the first date. I don’t care how many years you have successful worn them – don’t do it that day or night. Why not? Because, you’re probably already dealing with nerves and you don’t know where you will wind up or what you’ll be doing by the end of the night.

For instance, if your hot date decides he wants to go to the State Fair – instead of going to your pre-planned dinner at an upscale restaurant – then what? You’ll be “cribbling” or “wobbly walking” all night in those stilettos. Yeah, that’s not a great way to make a stellar first impression. Stick to cute low pumps, wedges, sandals, or flats.

Men, please make sure you have on a nice pair of loafers or dress shoes for your first date. And, please make sure your shoes are CLEAN and not scuffed-up. Why? Because, most women find that unattractive.

Polish those shoes and get rid of the dirt and “scuffmarks” before your big night. If your shoes are cruddy, your date may wrongly assume you are just as cruddy, so make sure your shoes are nice and neat. Stay away from tennis shoes – at least for this one night.

Unsure of what types of shoes to wear with certain outfits? You are in luck because you can find some swoon-worthy suggestions right here.

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About the Author

Dr. R. Y. Langham

Ph.D. in Family Psychology

Ree has a Master’s in Marriage and Family Therapy (M.M.F.T.) and a Ph.D. in Family Psychology. She spent over ten years counseling families, couples, individuals, and children on adjustment issues such as blended families, same-sex couples, dysfunctional family relationships, relationship issues, etc. Now she writes for famous health organizations and is a published author.
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