Sometimes, it’s best to leave the trickiest sartorial situations to the experts. Case in point: dressing for a first date. Cue Greta Tufvesson and Nikki Lewis, co-founders of exclusive matchmaking agency The Bevy. We recently lunched with the matchmaking experts to learn the dos and don’ts of dressing for a first date, dating tips, and more. For example, are flats acceptable for date number one? Should you really wear bright red lipstick? Check out all their honest answers, right this way.
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Do men typically prefer a dress or top and pants for a first date?
“You know what your assets are. Go with that. If you’ve got killer legs, rock a dress or skirt. If you’ve got curves to kill up top, go with that and maybe some dark skinny jeans. Never reveal both legs and bust—you must leave something to the imagination.”
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Are flats okay for a first date?
“Under no circumstances are flats okay on a first date unless he is your height. Heels boost your confidence and make you feel sexy. They also make your calves and ankles look good.”
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What about jeans?
“Jeans are allowed, but they should be dark, form-fitting, and have a skinny ankle (men love ankles!). We’re all about ripped boyfriend jeans and heels, but that’s too Man Repeller for a first date.”
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What’s the outfit combo you can’t go wrong with for a first date?
“With fall approaching, heeled booties or pumps with a miniskirt and a tailored leather jacket would look killer. Or, if you want to feel more comfortable, replace the miniskirt with skinny black or indigo jeans.”
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Are there any clothing pieces I should definitely avoid?
“Anything Man Repeller. Unless the guy works in high fashion, he won’t get it. Nothing baggy. He wants to see your figure. If you think Mary-Kate or Ashley have it, don’t wear it.”
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Can I wear lipstick on a first date?
“Stick to a nude gloss. Chances are your lipstick will get on your teeth, and he’ll be distracted and too scared to let you know.”
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Does the color of my nail polish matter?
“Nail polish absolutely matters. You should be manicured in a natural, nude, or light pink. A bold red is fine with fall approaching. Loud colors like green, blue, or orange are a deterrent for most men. Men are highly sensitive to nail polish color. Anything goes on your toes!”
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How should I wear my hair?
“If you’re particularly excited, go for a blowout! Wear your hair down. Stick with styles that are typically feminine and beautiful.”
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Perfume or no perfume?
“Perfume is awesome—yes. But don’t overdo it. Just a little behind your ears should do.”
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Are there any style icons or celebrities I can look to for first date outfit inspiration?
“Olivia Palermo is a style goddess and looks good in everything. Diane Kruger is also stunning and always looks tailored. If you’re a more girl-next-door type, channel Rachel Bilson because she always looks immaculate.”
Keep scrolling to shop first date pieces!
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JOA Knit Dot Print Dress ($99) in Ivory
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Bobbi Brown Lip Gloss ($25) in Nougat
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Equipment Adalyn Blouse ($258) in Gray Violet/Bright White
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Current/Elliott The High Waist Stiletto Jeans ($184) in Jet Black
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Deborah Lippmann Nail Polish ($18) in Taupe
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Reformation Corsica Dress ($218)
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Schutz Odelia Haircalf Mules ($180) in Black
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Oak Rider Leather Jacket ($630) in Black
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Isabel Marant Adelaide Wool-Blend Wrap Mini Skirt ($505)
What’s your biggest wardrobe dilemma when it comes to dressing for a first date? Let us know in the comments below!