One of the most monumental questions a fashion-conscious woman asks herself leading up to a first date, meeting the parents, meeting his friends, and all the other dating milestones is “What should I wear?” And it’s no wonder; first impressions are extremely important in relationships and can make or break how someone sees you.

Yael Kanter, Creative Director of and Fashion Consultant for tells us what to wear and what not to wear for these dating milestones in relationships.

1. First date dos and don’ts

Whether you’re going on a first date or meeting his parents, Kanter says it’s always best to be authentic with your wardrobe. “Don’t try to be someone who you’re not. Don’t wear something you have never worn before, that is too fussy or complicated,” says Kanter (there is nothing worse than being stuck in the washroom trying to zip something up for 20 minutes on the first date, as he wonders why you have been in there so long). “I believe in a blazer and a piece of great
statement jewellery. You can throw it over your most comfy outfit and you will look polished and feel confident.” With a basic t-shirt and pair of jeans underneath, you will be all set. Her favourite jeans for a first date are anything high waisted by J Brand, especially their ‘Mariah’ style in a dark wash. “Stay away from light wash,” she says, or anything low waisted that can provoke muffin-top situations.

2. Rules for accessories

In true Coco Chanel spirit, take off one piece of jewellery, because you always over-accessorize, says Kanter. Instead of playing around with bracelets and rings that can be noisy and distracting, she suggests you use stick with a statement necklace. “A statement necklace is right there, it’s up front, it draws people to your face,” says Kanter who adds that the necklace can show your personality, whether it’s antique, brightly coloured or a family heirloom. “Lots of people think a statement necklace has to be really, really huge, but it can be a delicate layering of a simple necklace, or a string of pearls. That’s a statement,” she says.

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More tips for what to wear for dating milestones on the next page…
3. Meeting his friends

The biggest need-to-know when putting yourself together to meet his friends? “Know your audience,” says Kanter. “First of all, find out what they are like. If they’re into fashion, you dress more fashion-forward.” Alternatively, if they are sports buffs and you’re going to cheer on a hockey team together, dress down for that occasion.

4. Formal occasions and family celebrations

Don’t go reaching for that safe LBD so fast. Kanter says “I break the rules when I go to weddings, I don’t think there’s anything wrong with wearing hot pink, bright blue or a beautiful colour. All eyes will be on the bride anyways.” Her advice is to flirt with the idea of a
coloured dress, or if that’s too much of a stretch for you, try a brightly hued clutch or pair of heels, or belt. “You want to stick out, you want to show his friends you aren’t just a wallflower and that you do want to have fun and you do have a fashionable side. Everyone else is going to be wearing black, it’s a cop out,” says Kanter.

5. Faux pas

Now that you know what to wear, Kanter emphasizes what not to wear. On her “don’t go there” list are: halter tops, shorts that are too tight or show more than they should, and anything that exposes your midsection. And though she admits, “I equate lipstick with being a lady,” she suggests you avoid anything too crazy on your lips (the lipstick on the collar thing really does happen).

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How dating against your type can result in a relationship

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