Never Wear This on a First Date, From a Matchmaker

Dacy Knight


Dressing for a first date can be a bit daunting. You only have one chance to make a great first impression, so whether you've been set up on a blind date or both swiped right, your first date outfit can play a big role on the impact you make. Too often when it comes time to dress for a first date, we try on a series of ensembles, second-guessing our style and eventually hating everything in our wardrobes. First dates are anxiety-inducing enough without the pressure of picking the "perfect outfit." So to alleviate the sartorial stressors of future first dates, we called in a professional for a lesson in first-date dressing.

We reached out to seasoned matchmaker Sherry Singer—previously on The Match Off and now running her nonprofit Sherry's Ark to build permanent housing for the homeless throughout California—to spill her first-date dressing rules. Singer's number one first date outfit combo is heels with jeans and a beautiful top. "You can look beautiful in jeans and a blouse at any age," says Singer, and this straightforward formula allows for variations in style, age, and level of dressiness. But even with the ideal first date outfit there's breathing room. If you'd rather not wear heels, Singer says boots, even flat ones, work just as well as long as they're fashionable. Not into jeans? "If you are a dress girl, definitely wear that dress," says Singer. For an outing on a colder night, Singer swears by three jacket staples—leather, military, and a stylish blazer. 

Too noisy is distracting and you're not focused on the person.

Sherry Singer

As for the pieces to steer clear of? Singer says there's one colour to avoid wearing on a first date. "Definitely not orange," she says. "I think it's distracting." Instead, seek out colours that complement your skin tone. Light and even bright colours pop on darker skin and deeper shades look lovely on fairer skin. If you're wearing prints, Singer advises that they not be too busy. "Too noisy is distracting and you're not focused on the person." The same rule goes for jewellery, which Singer notes "should always be conservative—not too loud, not to big, not too bold." It's best if your accessories complement your outfit rather than making their own statement. "When you're going on a date you want to focus on the person, not the jewellery," explains Singer. "You want them to say, 'That looks nice on you. Now tell me more about you.'"

Head below to browse matchmaker-approved date night picks.

Shop Our Favourite First Date Pieces

Want more shopping picks? Follow us on Pinterest. 

Add a Comment

More Stories