Wanting to look good in public has to do with the respect that I have for myself and the respect that I have for the people around me. One of the things I love about New York City is how much people dress up for one another. Walking down the street is such a pleasure, because people are really turned out. Yes, it probably took them more than five minutes to get ready, but it was so worth it. They make the city a prettier place.

In her wonderful memoir D.V.,Diana Vreeland (who was born exactly fifty years to the day before me—lucky me!) talks about how she prepared nightly for the arrival of her husband. She dressed up for him every single night:

Isn’t it curious that even after more than forty years of marriage, I was always slightly

shy

of him? I can remember his coming home in the evening—the way the door would close and the sound of his step … If I was in my bath or in my bedroom making up, I can remember always pulling myself up, thinking, “I must be at my very best.” There was never a time when I didn’t have that reaction

—ever.

That’s kind of lovely, I think. It’s always better to err on the side of beauty over comfort. It might get tiresome in practice, but it’s a sweet idea. And it’s certainly better than being the dowdy, depressing, slatternly housewife played by Shirley Booth in Come Back, Little Sheba.

People who are lazy about grooming make me a little crazy. And I’m not talking about getting a blowout or putting on a ton of makeup or getting a haircut every week. I’m talking about bathing and other basics. What are you saying about yourself and about your feelings for the people around you if you give up on these simple things? You’re saying, “I don’t care.” And if you don’t care about yourself or the people around you, why should others care about you?

Grooming inappropriately can be as bad as not doing it at all. One time I was out to brunch, and a patron at the restaurant started clipping his nails. He was even with someone, who you’d think would have stopped him! It’s such a distinct noise. My gag reflex kicked in. When you see it on the subway, it’s bad enough, but at a restaurant? There was a lot of eye contact around the room, but the staff didn’t throw him out. He just finished, and then left the clippings there on the floor for the staff to clean up. That’s in my bad behavior hall of fame, and it’s a good example of someone being far too comfortable out in public.

I also question people’s definition of “comfort.” Sure, oversize T-shirts feel soft on your body, but you know what’s genuinely comfortable? Being dressed appropriately for your surroundings. It feels good at the end of the day to take off your fancy shoes and put on your slippers, but it also feels good to know that all day you looked good and smelled good and that the people you encountered had a positive impression of you and enjoyed having you around.

For my job with Liz Claiborne Inc., I host a ton of shopping mall events. I’ll be honest with you: I love them. My colleague Leah Salak and I do Liz Claiborne Inc. multibrand fashion shows for the shoppers at the mall. We pull clothes from the mall’s own stores so the customers can actually buy what they see. It’s fun and it’s also intended to be educational. We show people how they can mix and match, how they can take a dress from day to night, and how an item of apparel can be made ever more versatile.

We work with five to seven of our brands, which include Lucky Brand Jeans, Kate Spade, Juicy Couture, and DKNY Jeans. I always mix them up as much as possible. The business-side people always complain about mixing and matching on the runway. For them, taking a Kate Spade dress and putting a Juicy Couture coat over it is some kind of sacrilege. But I’m very blunt: People don’t wear one designer head to toe. So we show people how they actually will wear things, and ultimately, I think it benefits all the brands, because you see how versatile each item is.

Then we have a Q&A session after, and I always find it so touching how women will stand up in front of eight hundred to a thousand people, open up their jackets, and say, “Tim, look how thick I am through here. How can my clothing help me with this?”

It’s so wonderful how comfortable they are talking to me about these things. I love hearing about real people with real issues. We live in a bubble here in New York. Of course, I mostly like the bubble! But I also like to get out of it for a reality check, and the reality is that a lot of people are not comfortable with their bodies and need a little help making what they have work for them.

Maybe it will be helpful to hear that even in New York, the women who are supposed to be fashion idols aren’t happy with their bodies. When I’ve gone to the Vogueoffices I’m always struck by how insanely thin everyone is, even the editorial assistants, who aren’t in front of a camera. I think: How many eating disorders are there on this floor?

One former editorial assistant I know says that even though she’s a healthy weight and height and usually wears a size 8 or 10, she felt morbidly obese while she was working there.

Isn’t that a sick statement on the industry?

There is a famous cafeteria in the Condé Nast Building, which houses Vogue, The New Yorker, Glamour,and a ton of other magazines. It’s a feat of architecture, and yet everything about it horrifies me. Everyone there is so thin, and no one is eating the gourmet food on her plate. There are skinny mirrors on your way out. You know, throwing up your food is not healthy, just as obesity isn’t healthy.

I’m always saying I have the greatest respect for whatever size a woman is. We can work with whatever we have. To larger women who want to feel good about their bodies, I’m always talking about the opera divas—those big, beautiful, proud women who are so sexy and powerful. It’s ridiculous that a woman with that kind of build wouldn’t celebrate it. I know I find curves attractive on women, and most of the men I know do, too.

Of course, I also want people to be healthy. The girth issue in America is not about the clothes. You can dress the opera divas, and they can look great. It’s about health. I know how hard it is to lose weight when you drive everywhere and fast food is so cheap. For what I pay for a deli wrap sandwich across the street, I could go to McDonald’s twice, and that makes a big difference if you don’t have a huge food budget. But you have to find a way to stay healthy no matter what your budget is, whether that means exercise or cooking fresh food.

If a very overweight woman asks me to dress her body, I will say, “You can’t remain 450 pounds. Forget about picking the best clothes for your size; we can always help you look your prettiest, but it’s just not healthy to weigh that much.”

For the last three seasons, I’ve worked with finalists of The Biggest Loser,helping the contestants to dress their new bodies. They’re still not small, but they’re certainly half the size they were. And they are so much healthier. But they are faced with a fashion conundrum, because most of them haven’t even been in a department store in years. They’ve just been home in their sweatpants. Now that they have so many decisions to make, they find the amount of choice almost debilitating.

These inspiring individuals are wonderful to work with, but I will say the men are often very difficult. They don’t want to try anything new. They don’t know what looks good on them, and they get into ruts. They don’t want anything that remotely fits. “It’s too confining!” they cry. “It’s too constraining!”

I have to say to them, “Listen, sister. Get over it. That’s what it feels like when a pair of pants fit.”

I’m always shocked by how conservative people can be when it comes to their looks. The worst hairdo ever was the eighties puffy bangs. It wasn’t good then, but everyone had it, so you could kind of forgive it. Now there are no excuses.