Adam Glassman
Photo: Robert Trachtenberg
Q:  Is it worse to dress too boringly or too young?

A: Too young. It's off-putting to see a short, body-flaunting dress on a woman with an older face, even if she has a good shape. 

Three rules for age-appropriate shopping: 

1. Don't buy anything that makes you look foolish. Trends generate buzz and new business, but you must resist—fashion extremes aren't smart. This season everything on the runway was very short, even landing at midthigh. Ignore this. A long, gauzy skirt is sexier.

Adapt the classics. I find nothing boring about great suits, terrific dresses, beautiful skirts, and higher-rise trousers or jeans. French women (who seem to be born chic) wear the same blazer and pants for years, updating them with accessories—cute shoes, stylish bag, Hermés scarf—or a top in a fresh print or current color.

Support resort. December–January resort collections are often more sophisticated than summer lines; if you wait, you may find nothing in stores but slipdresses and minis.