Cool Mom vs. Cougar
"I'm a young-looking old married mom with a 6-year-old. Lately, my usual Wasp uniform of khakis and a twinset with loafers has me feeling frumpy, but the cougar look creeps me out. Can you suggest a new spin on effort-less, casual chic? My goals are to look age-appropriate but not dumpy, 'done' yet not 'overdone,' mother-in-law-approved without looking like my belle mère."
Please trust that there is no reason on earth for you to run from your current look to become a cougar! I love the Babe Paley/CZ Guest Wasp look. What you'll notice about those ladies is that they don't pin themselves in with a crew neckline, as you're probably doing with your twinsets. Rather, they open up their tops to create an elongated V that shows a little cleavage. The area above the breasts is a stunning asset that most women shy away from. Don't! And make certain that your khakis are a classic silhouette (no capris, please) with neither a taper nor a flare. Pair the khakis with a beautiful white shirt (think Carolina Herrera), and trade in the loafers for any of the many beautiful flats out there.
Keeping the Faith
"I am an attorney. I'm also an Orthodox Jew, and therefore dress modestly (covering my collarbone, elbows, and knees) but do not wear slacks. Can you suggest some stylish professional looks that also respect my religious traditions?"
As a resident of New York City, I know a number of women who share your issue. Trust that you have many options available to you. Given your work, I expect that you desire more classic clothing without frills and flourish. A sheath dress paired with a slim-fitting cardigan is a great look, and a belt can be added to give the shift some shape. Suits are another great option, but I suggest that you mix and match the jackets and skirts to avoid looking too stuffy. I don't know your color preferences, but please consider a rich aubergine. It resonates power without being too overt.
"I'm interested in the new military trend. I bought some cargo pants, but I don't know what to wear with them. What kind of top? Shoes? Should I wear manly or feminine accessories?"
I love the revival of military-inspired looks, too—the trench, the peacoat. But I must confess to you my concern for cargo pants (or worse, cargo shorts). Why? Those hip pockets and ancillary trim generally make the leg look wider than it is. But if you must, pair the cargo pants with a sleek camisole and a fitted denim jacket, or any other item akin to the military milieu. Owing to the masculine nature of the look, I suggest feminizing it with light and buoyant jewelry—gold or silver filigree as opposed to stones or large costume jewels. Finally, pair this look with flats only. Anything with a heel will look ridiculous.
GOT A STYLE DILEMMA? Send Tim your questions at marieclaire.com/asktim.