Answers to your pressing fashion and beauty questions from resident know-it-all Jean Godfrey-June.
Q: I have these awesome brown suede Jil Sander desert boots. What on God's green earth do you wear with desert boots? Anything long makes me look like a polygamist, and anything short makes me look like a wannabe hipster. A: The desert boot holds a special, wear-it-with-anything place in my heart: I lived in Italy during a moment when its entire population was consumed with a craze for desert boots.
Q: Why am I such a klutz with eyeliner? A: Two things to think about: I could not figure out eyeliner until I took a group class at Trish McEvoy. There I learned to take a flat brush and dip it in dark brown eyeshadow.
Q: Every holiday season I have the urge to buy something sparkly. Problem: I wear the piece once and retire it to the back of the closet once the champagne glasses clink on New Year's Eve. A: The great Gigi Guerra, former Lucky operative and now super-important Madewell marketing director, solved this problem for me once and for all several years ago.
Q: I don’t have huge breasts—and I like it that way. But all the unpadded un-pushup bras are super un-sexy. Help! A: It’s true. It’s a challenge to not look like the missing Girl Next Door if you want any kind of support in this world.
Q: Should you or should you not cover up a breakout? A: Makeup artists often give the deeply unhelpful and uncheering advice that everyone can see it anyway so why try to cover it up?
Q: I’m 27 and don’t look old enough to buy beer. Is there makeup that can help me look less preteen? A: Tasteful neutral eyeshadow plus a sweep of bronzy blush is sophisticated in a way that screams “I voted in the last election!”
Q: I’m a total heels girl. What looks good with flats? A: Flat sandals and/or boots, somehow, can be just as sexy if not sexier than heels.
Q: What colors/prints should girls with curves stay away from? A: Clothes with large, loud prints will make anybody look like a sofa if they’re too tight—and like hotel drapes if they’re too loose.
Q: When you're over 40, how short can dresses and shorts be? A: What you can wear—despite the 700,000 magazine articles that insist otherwise—depends only on your body and your mind.