Tim Gunn: How to Wear Vintage Right

Past perfect

"I love vintage dresses from the 1950s—they're flattering and really cute. How can I wear them in my daily life without feeling like I'm in a costume?"

I'm delighted by your question because it's an extremely relevant one. The key to keeping great, stylish dresses looking modern is to use on-trend accessories when putting together your look. Furthermore, your hair and makeup need to be current as well, or you'll risk going full-tilt Dita Von Teese. My good friend and coauthor of Gunn's Golden Rules, Ada Calhoun, is a die-hard vintage shopper who has a reverence for '50s style. She always looks relevant by styling vintage dresses with wide patent belts or a chic jacket. Carry an on-trend handbag and wear contemporary shoes and you'll look fabulous!

Fashion on a Budget

"I am a recent college graduate looking to work for the government. I'm a bit of a fashionista, on a budget, and would like to channel more feminine features into the masculine looks, which seem to be Capitol Hill staples, without breaking the bank. Where should I shop?"

I've spent a fair amount of time on Capitol Hill—I'm an ardent advocate for the Design Piracy Prohibition Act, which will give fashion designers intellectual property rights, and I'm working with the Council of Fashion Designers of America (CFDA) to put the DPPA before Congress. I've seen a lot of positive fashion changes since the Obamas have come to town. Now, I believe in being budget-minded when shopping. I find that more fashion mistakes are made by people with deep pockets than by those who shop more thoughtfully and strategically when adding new items to their wardrobe. Investigate the private labels of the major department stores (they're fashionable and more affordable because they're developed within the company) along with J.Crew, HM, and other accessible and attainable retailers.

Golden lobes

"I have keloid skin and can't have my ears pierced. I never really wear earrings because most of the clip-ons I find are dowdy and matronly. Any advice to help me accessorize my wardrobe with chic earrings?"

My sister doesn't have pierced ears, either, and like you, she bemoans the dearth of options in stores. I've been buying her clip-ons from Monet, which has everyday hoops as well as flashier pieces for special occasions. I also urge you to explore vintage styles with screw backs. They may not be the most comfortable, but vintage pieces can be quite exquisite and are often one of a kind. For more subtle, comfortable studs, consider magnetic backs. The impact of a pair of pearl earrings, no matter how they're attached to your person, will always be timeless.

GOT A STYLE DILEMMA? Send Tim your questions at marieclaire.com/asktim.