Jill DeBernardis after shot

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After

The rescue: Pucciarello gives DeBernardis a shorter, more flattering cut, bringing her hair off her face to highlight her cheekbones. Glassman replaces her sweats ("After a certain age, you should not be wearing Barbie pink") with slimming, neutral corduroys and a T-shirt in stand-out citrus green. A leather trench is a grown-up, well-priced staple DeBernardis can wear for years, to the grocery store or out to dinner.

To graduate from sweats:
  • Stretch corduroys are as comfortable as drawstring pants but can get you through a PTA meeting, a carpool, or a lunch date.
  • Invest in a versatile trenchcoat in gray or khaki to give polish to your casual daytime look.
  • Consider putting on proper pants and a shirt, even if you work from home. You'll feel more motivated—and inspired to do it each day.

Corduroys, J.Crew, $80. T-shirt, Lilla P., $58. Trench, Banana Republic Heritage, $398. Earrings, Julie Collection. Bracelets, Bounkit. Belt, LAI. Watch, Tag Heuer. Shoes, Musette.

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