'Ladylike dresses' for the 30s and 40s

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Stacy says a woman in her 30s wearing a "ladylike dress" similar to Mamie's can afford to show some more skin. From Saks Fifth Avenue she chooses a plaid dress by Nanette Lepore with a sweetheart silhouette that reveals a little cleavage and shoes by Dolce & Gabbana. "This kind of plaid is a neutral pattern," Stacy says. "In other words, you can pair this with a bright color if you wanted to. Or from far away, it's going to read as a solid, so you can add another pattern in if you wanted to do a pattern."

For a woman in her 40s, Stacy chooses a ladylike dress ensemble by 3.1 Philip Lim, available at Nordstrom, that emphasizes the waist while camouflaging problem areas. "In your 40s, that's when things start to spread, right? Your hips, your arms start to sag. The girls go south," Stacy says. "The idea is that this is still a flattering silhouette, still waist-conscious."

The main thing for a woman of any age to focus on when buying a "ladylike dress," Stacy says, is the waist. "This is a trend that you're going to see season and season again," Stacy says. "The idea here is that you want to show off your curves. If you pay attention to your waistline, you will always have a flattering silhouette. That is what works for women as long as the girls are up there where they should be."