Michael Kors is a great judge, and I think it’s partly because he does such clean, elegant work that he has a great ability to let the designers be themselves and not project his own taste onto them. (Friends of mine who love to wear lavish jewelry are big fans of Michael Kors dresses, because his clothes have such simplicity that they make a fantastic frame for baubles.)

He and Nina Garcia play so well off each other, because they both have a great eye, and they aren’t afraid to say what they think. There’s a great exchange in Season 7 when Nina throws her arms up about a neckline treatment.

Michael says, “Nina! How many necklines do you ever really see? I can count them on one hand!” The two of them have a big debate about how much innovation is possible when it comes to necklines. The Fairchild Dictionary of Fashion(my bible!) devotes ten pages to necklines and collars, but the truth is that clothes today typically feature only a few different ones.

I love these kinds of specific conversations about fashion. It really gets at the heart of these choices the designers have to make, and it’s so satisfying to listen in on these two important fashion people talking about it. Their squabbles are very instructive when it comes to how the design world approaches a burning issue like the boat neck.

It’s a lot harder than it looks to be a judge. And when we have designers as guest judges, it’s often hard for them to keep their own aesthetics in check. Most designers are incapable of understanding any aesthetic other than their own, and they want to impose it on the designers. Unlike most designer judges, Michael is really terrific about seeing each designer on his or her own merits. It’s a rarity.

Nina has a great eye, but there was one time she championed a dress that everyone else hated, and that I would say belonged in the monkey house. Perhaps you’ll recall the green neoprene dress Ra’mon Lawrence Coleman made in Season 6. He was dyeing it in the toilet before I suggested he take pity on the model who had to wear it and switch to the sink. The dress, a hot green mess thrown together at the last minute, was a disaster.

Well, Nina had a forty-five-minute filibuster for the neoprene dress. Nina is so tough and cool that she has the capacity to intimidate Heidi (and all of us a bit, truth be told). Nina’s trump card was her crystal-clear assertion that she would wear the dress. With that said, Heidi went along with it, too. Well, the look I thought was going to send Ra’mon home ended up winning the challenge for him. I couldn’t believe it.

Project Runwayauctions the winning looks of each season, so I bought the dress for Nina. It went for $305. When it arrived in a little cardboard box, I couldn’t believe how tiny it was, just two pieces of neoprene sort of glommed together. Seeing it up close was very illuminating. There were yellow pins sticking out of it, rough edges, spattered dye—and I still haven’t figured out how to assemble the top. Thank goodness I won it rather than some fan, who would have gotten that package and declared, “This won?”

I’m planning to send it to Nina with the suggestion that she wear it for the next event we have to do together. I have a feeling she won’t.

In any case, what keeps the show from turning into one big monkey house is the seriousness with which our judges take the matter of construction and design. During the runway show there is a huge amount of deliberation, far more than most people realize. From the moment that the judges see the work on the runway to the moment Heidi says who’s in and out, five to six hours elapse, not the several minutes you see at home.

I’m frequently wrong not just about who will be chosen as the winner, but also about who’s in the top or bottom three. Sometimes it flips while they’re deliberating. The judges change their minds a lot before they reach a verdict, which I believe is positive and a great testament to the seriousness of their discussion.

Guest judges are real wild cards when it comes to what they like. Sometimes a guest judge will say, “This was my favorite look!” And all the others had it as something that justified sending someone home. That’s why Heidi rarely asks the guest judge to speak first anymore. In the make-each-other-over challenge in Season 2, Santino Rice’s jumpsuit for Kara Janx might well have sent him home had Freddie Leiba not said right off the bat that he loved that look.

It’s all edited out in the final show, but one guest judge told the designers what she would have done had she been designing for the challenge. “I would have picked this fabric, instead! I would have designed it this way!”

That is not helpful. The competing designers didn’t use that fabric or that silhouette, so how can you judge them on what you would have done rather than on what they did in fact do?

In the finale of Season 3, Nina Garcia, not I, was scheduled to give the designers a critique early in the week. But because of the whole Is-Jeffrey-cheating debacle, she came in late on Thursday, instead. The Bryant Park fashion show was going to be held the following morning.

When I arrived after the critique, I asked the producers, “How did it go?” and they said Nina had given the designers a hard time. I was disappointed to hear that, because I thought, What are they going to do? The show is tomorrow. At this point in the game, negativity isn’t helpful.

So I did my routine for the camera, and then I went back to the designers and said, “I heard the visit was hard.” Everyone shrugged. Laura Bennett looked up and wisely said, “As if we could do anything! We didn’t even listen.”

She was correct. Sometimes it’s just too late to rethink and rework, even if the advice is brilliant.

Which brings us back to something I keep finding myself saying in this book: Context is everything—for clothes, for behavior, and for expectations. Truth telling is good, but you also have to accept the conditions as they are.

When someone is about to head onstage or on camera, do you tell her she has parsley in her teeth? Absolutely. That is helpful. But do you say, “That is a terrible dress”?

No! There’s no time to change, and she’ll just go out there feeling bad about herself. Similarly, I stop making comments, especially comments that suggest that an item should be reworked, the day before Bryant Park, because negative notes aren’t helpful at that point, unless you’re addressing matters of accessories or styling or the looks’ order on the runway. To suggest starting over is no longer feasible.

The question I ask myself before giving advice is: Is what you want to say really going to help them?

Sometimes it’s very clear. For example, recently I was doing an interview on camera. The interviewer’s lapel was sticking up, and I could tell it wasn’t just a jaunty affectation, so I said, “Before we start, let me fix this,” and I adjusted his collar.

“Thank you!” he said, rather relieved.

“I’d want you to do the same for me!” I said.

If you’re getting dressed with a friend, you can say, “You should rethink those shoes.” But you need to have supplies available! When Leah Salak, a colleague of mine at Liz Claiborne Inc., and I do shopping mall events together, and she asks, “How do I look?” I take the question seriously. People are videotaping these events, and there are thousands of people in attendance. I don’t want her to regret anything later. And we have a ton of options around here at the office, so I can say, “That cut’s not quite right for you. Let’s see what else we have.” Then we can pick out something truly gorgeous.

Also, I give her advice because—and this is an important distinction—she asked.If someone doesn’t ask, you don’t have a moral obligation to say every thought that pops into your head. As I’ve mentioned, strangers are constantly saying to me, “I was so afraid of what you would say about what I’m wearing!”