How to Dress to Meet a Boy for the First Time

Co-authored by Christina Jay, NLP

Last Updated: May 19, 2024 Approved

Meeting someone for the first time comes with a lot of questions. The first question you may ask yourself is, “What should I wear?” Learn a little about the boy you are meeting and what you will be doing to help you pick the right outfit for the occasion, then let your style shine.

Method 1

Method 1 of 3:

Dressing for the Occassion

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1
Research where you will be going to meet him. When you are trying to decide what to wear it is helpful to know when and where you will be going. You dress differently for church than you do for school than you do for the club. In the same way, it is good to know what is considered acceptable for the place you will meet. Your outfit will be influenced by your surroundings.
- Look the place up online and find pictures to see how fancy or casual it is. Look for pictures with other people in them to give you an idea of how people tend to dress there.
- Swing by the place before you meet him so you can get the vibe in person.
2
Adjust to the time of day. The time of day you will be meeting is also going to affect what you wear. Beyond dressing appropriately for the temperature, there are differences between daytime and nighttime clothing.
- Daytime calls for light or bright colors and a more casual style with less jewelry. You can still wear a dress, but tone it down to a simple shift, shirt dress, or wrap dress.
- Meeting at night means a more formal style like that little black dress with some heels and that one piece of eye-catching jewelry.
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3
Balance casual looks with class. If you decide to dress casually, you want to be sure you still look put together and not sloppy. Combine very casual clothing with something a little fancier to keep the casual in check.^{[1]
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- Make distressed jeans work for you by pairing them with a nice pair of black heels and a sweater or silk blouse.
- Combine an oversized shirt with something fitted like tights or leggings so your outfit doesn’t look baggy or ill-fitting.
4
Avoid covering a nice outfit with casual outerwear and accessories. Once you have put together the perfect attire for the evening, the last thing you want to do is ruin it by covering your nice dress with an old coat, or slinging your big, beat up handbag over your shoulder. Think ahead when it comes to the necessities and make sure they enhance your outfit instead of detracting from it.
- Black leather jackets have style and class, and go with almost anything. They are a great addition to your wardrobe.
- Accessorize with a hands-free purse like a clutch or wristlet. These look more sleek and sophisticated than fussing with a large bag. If you need more space to carry things, use your jacket pockets.
5
Wear comfortable shoes. Medium to low heels and flats are fine for a casual look. When you are going for formal, heels can look great, but also can be terribly painful. When you are choosing heels the fit is just as important as the fashion. Choose a heel which is comfortable on your feet and easy to walk in.
- Avoid heels which are incredibly high. Not only may they be difficult to walk in, but you might tower over him if they are too tall.

Method 2

Method 2 of 3:

Projecting Your Personality

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1
Decide what impression you would like to make. Based on what you wear, he will assume things about your behavior, character and attitude. Little tweaks in your outfit will send signals about who you are.
- People who dress more formally tend to be perceived as smarter, and more successful.
- People with a more casual look come off as friendlier and more adventurous.
2
Ask your friends for their opinion. You know what the outfit means to you, but the perceiver could form an entirely different opinion. Choose a friend or two who you know will be honest with you and ask what they think of your outfit. Don’t just ask if they like it, but ask what impression they get from you when you are wearing it. What would it say about you if they had never met you before?
- Try asking a guy friend so you can get a male perspective.
- Get more than one opinion, because your relationship to different friends can affect their perception of your outfit.
- Tone the outfit up or down, or change it entirely and start over based on your friend’s response.
3
Incorporate items which group you with a certain community. If you know that you and the boy have similar interests, wear something which will bring you together. Certain clothing can identify you as being part of the group.
- If you are both really into music, you could wear a band t-shirt.
- Put on the necklace, bracelet or skirt you got overseas to show you are a free-spirited adventurer.
- Cowboy boots will give off the impression of a country, outdoors type. Doc Martens will set you off as more of a punk rocker.
4
Be true to yourself. Remember this is not all about him, it’s about you too. You want to attract the kind of boy that you like. Your outfit is part of your own personal branding and says something about you. Letting your personality shine through your outfit is going to help you find out if this boy is a good match right from the start.^{[2]
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- Stick with your normal style rather than trying to change your look for the first meeting. You want him to meet the real you.
- You don’t want to look completely different if the two of you decide to hang out again.

Method 3

Method 3 of 3:

Making a Good First Impression

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1
Learn as much as you can about him before you meet. People tend to react more positively toward people they can relate to, including people who dress more like them. The more you know about him, the easier it will be to appeal to what he likes. Think of a few questions you can ask to learn more about his personality and style.^{[3]
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- Ask where he grew up. Certain regions have different styles. Someone from Brooklyn may be more on the cutting edge of style than someone who grew up in the country in Montana.
- Ask what his hobbies are. If he spends time in coffee shops and record stores, he is probably more of a hipster. Someone interested in sports is probably more of a t-shirt and shorts type of guy.
2
Be confident in what you are wearing. There are already enough unknowns in a first meet. You want to appear confident. Now is not the time to try to put together a new outfit. Choose clothes you already really like, that make you feel good.^{[4]
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- Think about what outfits you have gotten compliments on in the past.
- Choose comfortable clothing which fits well. You don’t want to have to worry about adjusting yourself all night.
3
Stay near the middle of the road. Avoid wearing something that you think is too much of anything. This could mean it is too short, too tight, too flashy, or too boring. If you are already questioning it, don’t wear it.^{[5]
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- Save the daring choices for a later date when you want to spice things up.
4
Wear some makeup, but not too much. It’s sad but true that people react more positively to girls who are wearing makeup than bare-faced girls. It’s a double-edged sword, because that respect can also be negated if you are wearing too much makeup.^{[6]
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- Stick to just some powder, blush, mascara and lip color.
- Avoid excessive eye makeup or bold lip color for the first meeting.
5
Don’t sweat it too much. He may not be the type of person who puts a lot of thought, effort or money into his own clothing. If this is the case, he is less likely to pick up on clothing cues or really care too much about what you are wearing.
- If he does spend a lot of money or time on his outfit, then he is probably just as worried about how he looks as you are.

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How do I impress a guy on a first date?

Christina Jay, NLP
Matchmaker & Certified Life Coach
Christina Jay is a Matchmaker and Certified Life Coach based in Toronto, Ontario, Canada. Christina is the founder of Preferred Match (preferredmatch.ca), her matchmaking service that finds love for successful and elite individuals. She has over 10 years of coaching experience, earned her NLP (Neuro-linguistic Programming) certification through NLP Canada Training, and has a BA in Business Administration from Brock University.

Christina Jay, NLP

Matchmaker & Certified Life Coach

Expert Answer

Pick a stylish outfit! Go with an outfit and makeup look that complement your skin tone.

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The biggest thing to remember is that the guy is nervous too.

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Just remember to be yourself and most of all have fun. This way he will get to know the real you. Laughter can overcome all odds.

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