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  • Writer's pictureWhitney Wisdom

First Date Looks for Her


When Ivy Wang rocks a yellow skirt and a vintage purse.

Life Lesson #1: dress well and you’ll never feel awkward! And what is the social interaction we feel most awkward about? That would be first dates! The pressure of getting someone to like you enough over a quick din so they don’t fall off the face of the Earth the next day is just exhausting/scary/crazy/weird. Set yourself up for success by wearing an outfit that you love and maybe you’ll just find the love you’re looking for! Or not. Either way - you still looked cute! That’s a win in my book!

The Fit: Now that we’ve covered life lesson #1 let’s move onto rule #1 for first date looks. Wear something you’re comfortable in! This is surprising advice coming from moi, I know, but I also don’t mean, wear sweatpants. Wear something that fits you really well - that accentuates your assets. Don’t wear jeans that require you to suck it in because what if you pass out on the first date? Or worse, what if your pant button just flies right on off! You also don’t want to wear anything that is too short for comfort. I understand short is sexy but pulling up your shirt the whole night will distract you from the conversation and will ultimately cloud your judgment of whether you want to see this person again. Same thing with yanking down your skirt. Bodycons existed in the 2010s so they do not have to be worn on dates now.


The across the table view is VIP.

On the flipside, if you want to wear something more revealing and it is not going to annoy you then do it! First dates are low risk, low reward. I wouldn’t be too nervous of looking “try hard” or “thirsty” because this is the first meet up. Do what makes you feel hot because at the end of the day, you know you’re taking you home.


The Trend: First date’s are the best time to experiment with a new look or to test out a new trend. That’s actually the coolest thing about meeting new people. You get a fresh start! A blank space, if you will. It’s an opportunity to reinvent yourself with minimal judgment. There’s no: you used to always wear dresses for dinner, what's with the pantsuit, type remarks. That kiddie Y2K hairstyle you never thought you could pull off? Go for it! Your date should be flattered by all the effort you put into your outfit.


A little pre-date pump up music never hurts!

The Colors: If you’re confident in your current style and aren’t necessarily looking to reinvent the wheel I’d choose something in warm and inviting colors. Especially, if you’re going on a date with a man. Color is what men notice most about women’s fashion. (Obviously, I am stereotyping here because I have to. I don’t know your specific date and we love a man who’s interested in fashion. There just aren’t many of them.) Taken people: ever notice when you ask your significant other which top goes best, their answer is always a color. The purple one. If both tops you show them are purple then they are completely stumped on which to choose and say whatever you think. They only see color.


So which colors are the best for first dates? Happy ones! Send out the good vibes before you even open your mouth with a touch of yellow. A lot of people think yellow washes them out or is too bright and showy. You don’t have to wear a full yellow jacket (though it’d be hot), yellow accessories or a swipe of yellow nail polish will do the trick. Don’t expect your date to rave over how cool and different your yellow satchel is but, do know subliminally, it will make them feel joy. Yep, work the mind games from the start. Incorporating blue into your outfit will put your date at ease, letting them know you are trustworthy.


When you think happiness, I hope you think that long yellow dress.

Who doesn’t love an LBD? A first date that’s who. Challenge yourself to not go for the black one shoulder top everyone bought last summer. Black blends into a crowd, plus it is associated with death. I’d also pass on the love-signaling red because that is coming on way too strong for night one. Red is also known to signal danger ahead. Yikes!


The Secrets: Also, pro tip: if you’re actively dating and are going on a lot of first dates to meet all your potential matches, you can wear the same outfit each time. Perks: it's easier to compare the dates - who commented on your killer look v. those who didn’t while, eliminating the pre-date I-have-nothing-to-wear panic.


Romance blooms even on brick roads.

Personally, I have too many clothes. It would be a sin for me to wear the same exact garments each time but I do have a calculated formula. A tank or a tee (casual) with a mini or midi skirt (dressy) is the perfect level of trying. If you’re on the shy side or just getting back to the dating world, I recommend wearing a graphic tee with a band, movie, destination, etc. on it as an instant convo starter.


Always take a pic of the ‘fit because you never know when you’re about to go on your last first date.


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