By Cindy Weber-Cleary
Updated Aug 05, 2014 @ 5:02 pm
Credit: Getty Images

InStyle’s Fashion Director Cindy Weber Cleary has been a fashion editor for the past 20+ years. Needless to say, she’s picked up some tricks along the way. Catch her column here each week for how-to tips and style secrets on her favorite, timeless styles.

A few weeks ago I received a message from a Facebook friend in suburban Virginia whom I haven’t seen in almost 30 years. In college, her style was slightly preppy, but she was never really interested in clothes. She was, and is, very attractive and athletic (I did a quick survey of her photos) but clearly a casual dresser.

She told me that she had divorced a year ago and was asking me what she should wear on an upcoming blind date. I asked her what she knew about the man she was being set up with and where they were going to meet. She replied, “He’s a divorced lawyer and we’re meeting for a drink at a local restaurant.” That didn’t give me much to go on, but knowing that she wouldn’t be comfortable in anything too trendy, this is what I suggested: A sheer linen or light-weight loose sweater in a soft color, layered over a white cotton or satin tank with white skinny jeans, and flat strappy sandals or wedges (she doesn’t like heels). I suggested she push up the sleeves and add a stack of bangles or bracelets and a bag with “a little personality” (a contrasting color or pattern). Then I sent her some links.

It’s an easy look to pull off and I knew it would be appropriate in most suburban restaurants. I also knew she would feel comfortable, which is the most important thing in a slightly uncomfortable circumstance such as a blind date. The sheerness of the sweater worn over a tank has a subtle sexiness; the soft color is feminine and approachable; the skinny jeans, playful bag and strappy sandals suggest a youthful attitude. Finally, this look doesn’t telegraph too much about the person wearing it, which may sound like an odd consideration, but there are certain situations in which you want to look stylish but not make a big statement. After the first date, if all goes well, you can afford to let your light shine brightly, but until you know more about the other person, it’s not a bad idea to keep it low-key.

Well, guess what? There have been three dates so far and I even saw a selfie of them posted on her timeline! Turns out he’s kind of preppy and athletic too. Whoever made the introduction appears to have had good instincts—and I hope that my fashion advice helped in it’s own small way.

To start your first date outfit, you'll need some basics. Here are a few of my favorites:

Jeans: Levi's Mid Rise Skinny Jeans, $54,; Ann Taylor Curvy Ankle Denim Jeans, $89,; J.Crew Stretch Matchstick Jean, $105,; Paige USA Kylie Crop, $179;

White tanks: Josie Natori tank, $125,; ATM, $64,

For a complete look, here are some cute pairings:

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J.Crew sweater, $80,; Pierre Hardy clutch, $225,; Opening Ceremony sandals, $315,

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Vince sweater, $225,; Mansur Gavriel bag, $460,; Manolo Blahnik sandals, $675,

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Eileen Fisher sweater, $178,; Givenchy bag, $650,; Lola Cruz sandals, $225,