What Should I Wear on a First Date?

The excitement of a first date is the most amazing feeling! The prospect of a new relationship and all the possibilities it could bring. You managed to meet a great online dating match and they agreed to meet up with you for a night of fun. There’s only one problem, you have a closet full of clothes, but nothing to wear! Ugh!

We have all been there, and it can be nerve racking to figure out if you should wear the white t-shirt with the slight v-neckline or just the regular crew cut neckline. Decisions, decisions. Today we will unpack the right moves to make when deciding what to wear on a first date.

What to Wear on a First Date

When selecting an outfit for a first date, you want to remember to select an outfit suitable for whatever activities you will be partaking in. If you are going to an event at an art gallery, then flip flops and a t-shirt dress may not be the best choice. If you are going cosmic bowling, then be mindful of how certain materials glow through others.

If the activity is low key, then your outfit should reflect your low-key self. If the activity is dinner at a fancy restaurant followed by an art gallery opening, then you should opt for something more refined and classier. Use your discretion and select something that makes sense with the activity you will be doing.

Obviously, no one plans to spill something on themselves, but hey it happens, right? All you can do is make sure that when you meet up with your online dating match your shirt is clean and fresh looking. Be mindful of fabrics that need pressing or steaming prior to wearing due to their tendency to wrinkle.

Don’t be the person who shows up with their shirt looking half-washed unless you are really going for that hipster look. We all have our styles, just remember this is your first impression and you will only get one first impression, so make sure your shirt is clean. Your date will be looking in the direction of your shirt a lot, so it’s cleanliness is extra important.

Covering “it” up is not limited to what most might instantly think of, but yes, ladies we are referring to certain assets that. This is also in regard to tattoos, piercings, etc. You want to try and always leave something to the imagination. Nothing is more exciting than the wonderment of what might be hidden underneath that stylish outfit you selected.

IF you have a full sleeve (or two) of tattoos, that’s really cool, but it might actually be more of a distraction than anything else when first meeting your online date offline. Consider covering things like tattoos with a long sleeve or pushing up your sleeves to only slightly expose a part of the tattoos. This will become a point of interest that your date may inquire about seeing more of, instead of a distraction keeping them from gazing in your eyes.

You may not be wearing shiny shoes, but whatever shoes you are wearing you should make sure they are clean. There are a lot of great products to bring new life into a pair of shoes which have had many years of love (wear and tear). One really great tip for cleaning white leather or white rubber shoe soles is to use a glass cleaner product sprayed onto a paper towel. Voila! They’re like new again!

When we first meet someone, our instinct is to do a head-to-toe once over. Oh, come on, you KNOW what we’re talking about. Your shoes are just as important as your smile, and not having food stuck in your teeth.

There are so many style options out there to choose form for a first date. Going mini golfing in stiletto heels may not be the best choice, so remember to keep your outfit choice appropriate for the activity. Your date will spend a majority of their time looking at you and your shirt will be in their peripheral vision nearly the entire time, so try to keep it fresh and clean looking throughout the date.

Keep distractions like tattoos or even cleavage out of the situation. You can still show off parts of your tattoo to “tease” your date, and a tight shirt with a higher neckline can do a lot to make your “ladies” look great (and larger too). Remember that your shoes are going on the date too, so be sure to clean and polish them as necessary. Follow these simple tips and you’ll look great from head to toe!

Next Step: Guide to Meeting an Online Date for the First Time

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Author: Matt Seymour, MSF

Matthew J. Seymour is a dating industry expert with over a decade of experience coaching singles, reviewing dating apps, and analyzing trends within the industry. Matt is a published author with his most recent work “Get More Dates: How to Master Online Dating Apps” that hit shelves in 2023. With a Masters of Science in Finance (MSF) degree from the University of Florida and extensive knowledge of the innerworkings of the online dating industry, Matt frequently serves in an advisory role to some of the largest dating apps on the market. In Matt’s current role with Healthy Framework, he leads the interview team that regularly interviews key dating industry leaders, and leverages his financial knowledge and dating app experience to review and share what singles need to know to get the most out of dating online.