Getting dressed for a date is a deeply personal sartorial decision unlike any other. “This isn’t just going out with your girlfriends!” declares Maxine Waters, owner of Riant Boutique in Toronto. What you wear will likely influence how you carry yourself—and if it’s a first date—undoubtedly how you will come across. “You want to present the best version of yourself,” she says. “And ‘self’ is the most important word in that statement.”

Waters share the top rules of date dressing—plus never-fail outfit ideas for your big night.

1. Shop for pieces to wear with what you already own

Date night dressing typically follows this formula where going out with a new guy means shopping for a new outfit. But think in terms of pairing back to what you already own and love, and what you know leaves you feeling great. “Always have a killer pair of jeans that look the way you want them to look on you,” says Waters. As for other investment pieces, she suggests a classic leather jacket and a pair of go-to heels and flat boots, then mix and match accordingly.

If you have a nice jacket or blazer, then you can easily add in a new blouse for the big night. “Build your staples around it,” she says.

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2. Dress for the event
If you know where your date is taking you, be sure to dress appropriately for the occasion. For a meet-up at a pub over drinks, go for a cool, casual look. “Try a fun graphic T-shirt and leather jacket,” says Waters as one of her classic outfit ideas . Or if it’s a nice dinner, swap in a fitted blazer and silk blouse instead.

Show off your moves—and some skin—on the dance floor with a short-sleeve or sleeveless blouse and a cute jacket or blazer. Just but be mindful of your footwear. “No one looks good limping around,” says Waters. Go with a pair of heels that are cute but comfy—and that you’ve had practice wearing before.

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More date night outfit ideas on the next page…

date-dressing-rules-page-two.jpg3. Choose your most confident outfit
Choose an outfit that will relay your style and personality authentically. And wear it confidently. “That stands out more than what you’re wearing,” Waters adds. If the sales person or your BFF tells you an outfit looks great but you don’t think it suits you, then simply don’t wear it.

4. Consider height of your heel
If you’re going out with someone you haven’t met before, err on the side of a mid to low heel. This also works if you don’t know where the night may take you—an evening stroll, perhaps?—or if there’s just a lot of walking around involved.

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5. Have a gorgeous statement coat
We live in Canada and it’s pretty well cold here six months of the year—so it’s worth investing in a killer coat that not only keeps you warm but looks good. Besides, “it’s awkward showing up for dinner at a nice restaurant in a puffer coat. There’s no fluidity to your outfit,” says Waters. Go for a gorgeous wool coat (Mackage has beautiful double-duty style and warmth coats with leather detailing) that speaks to your style.

6. Dress to feel and look your best

“Don’t put yourself in something that you’ll be fidgeting in,” says Waters. Wise words: if something is too low cut or uncomfortably fitted, you won’t be able to relax and pay attention to your date.

Opt for sophisticated sexy as opposed to an outfit that’s too revealing. “You want to leave something to the imagination,” she says.

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7. Add accessories to complement your look

A T-shirt is one of those understated sleek, sexy outfit ideas—especially if you add a gorgeous
statement necklace over top. “It’s more exciting,” says Waters. Wear a fabulous statement watch or go with a beautiful scarf to wear over a sheer blouse.

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8. Don’t forget about comfort

Your outfit should have an element of practicality to it, Waters explains. “If you’re wearing a sheer top to a hockey game, it’s beautiful but you will freeze.” Instead, go with a pair of leather pants and a loose blouse—which is still chic and sexy, but you’ll be able get through the night comfortably.

9. Add the right bag

“I think it’s weird when people get all dressed up and then have this giant satchel—what do you have in there?” asks Waters. Keep your bag in line with the rest of your outfit to maintain balance. And invest in a standard, small-to-medium-sized bag to take with you on your nights out.

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10. Be true to your style

“Don’t wear something that’s going to wear you,” says Waters. Or that’s totally out of character with your personality. “If the night goes well and you end up dating, he’ll eventually figure it out.”

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