Tips & Trends | What to Wear On a First Date

Flowers and chocolates, red lipstick and romance.. Another year, another Valentine’s, come and gone. For some of us, it involved all the typical valentines day surprises; breakfast in bed, a nice dinner and some cheesy gifts. The other half of the world, Valentine’s day consisted of Netflix, PJ’s, the two most important men, Ben and Jerry, and dreaming of meeting that special someone.

A few days later in Starbucks, while sprinkling the perfect amount of vanilla powder in your latte, someone suddenly bumps into you and it goes everywhere. Furiously, you look up and see the most perfect smile staring back at you… how could you be mad at that? He offers to buy a new drink and you start chatting. Then the incredible happens, and he says, “can I buy you dinner, I’d love to get to know you.” A date! He’s asked you on an actual date – that latte spill wasn’t so bad after all! A million questions flying through your head, all coming down to the most important question of all, ‘What will be my first date outfit?’

The Date: Dinner For Two

You start with a salad and bruschetta to share, pacing yourself for a long night of food ahead. The main course arrives and you’re already feeling a bit full. You’ve ordered the chicken but he insists on trying the pasta as well. Just when you think you could not possibly eat any more, he orders dessert! This man’s stomach is bottomless!

The Outfit:

Wearing the pencil skirt may make you feel your best, but by the end of dinner you’ll probably be regretting it. For this first date outfit, try something a little more forgiving; a shift dress and a jacket to create the perfect mix of cute and sexy, with a bit of comfort for you too.

The Date: Sports Night

Your new guy is a huge sports fan with some serious home town pride. He scored two court side tickets to the upcoming NBA game and he’s hoping you’ll rep his team colours. You’re meeting him there and planning to go for drinks after the game at a near by bar.

The Outfit: 

Going all out in Raptor’s gear might not be your style for a first date outfit, especially if plans call for a martini lounge later on. Try to avoid being overdressed for the game or underdressed for drinks by throwing on a black tee with a pair of denim, a leather jacket and some booties. You can dress this look up a little with a statement necklace and choose a shade of lipstick that match the team colours.

The Date: Afternoon Hang Out

Saturday afternoon, you both meet at the city’s latest art gallery for a date filled with culture and inspiration. After admiring the beautiful artwork, he insists on taking a stroll around the area and finding a coffee shop to sit and chat your afternoon away.

The Outfit:

Walking around the city might get a little chilly, although art galleries are usually kept warm. Enjoy the best of both worlds by trying this seasons latest trend: lamp shading. Shed the coat while in the gallery and stay warm out doors by wearing a cozy sweater dress and knee high boots. This trend looks amazing either way and will make your first date outfit one to remember.

Let us know which look is your favourite, or if you have any first date outfit ideas and where you would wear them!

Designer Swap is Canada’s online luxury consignment shop and Toronto-based fashion blog. We sell authentic and pre-loved designer pieces and write about the newest fashion and beauty trends. Make sure to check us out on Instagram, Twitter, Facebook and Pinterest!

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Images courtesy polyvore.com, inanutshell.ca