Q: Give us the absolute essentials for a Tim Gunn vacation.

A: Well, I wouldn’t want to sit on a beach. I wouldn’t want to do anything where I would possibly end up in a hospital. That would ruin a vacation. So forget rock climbing and skiing. Scratch those right off the list. Give me any vacation where there are museums, history, good dining and paved roads. Actually, that’s not altogether true. I’d love to go to Angkor Wat, where they’re probably paved with a cobblestone.

Q: What wouldn’t you be caught dead wearing on an airplane?

A: A sweatsuit! Or sweatpants and a T-shirt. Some people get onto a plane wearing pajamas because they plan to go to sleep. On one hand, I kind of understand. On the other hand, you were just walking through an airport — it’s not as if you were arriving at the plane in some enclosed vehicle. So don’t you have the remotest bit of ego that says, “I at least need to look halfway decent and there aren’t 200 people sharing a bed with me?” I just don’t get it. If you want to dress as if you just got out of bed, don’t get out of bed.

What you love:

“Well done! The wheat and chaff have been parted. Only delightful pieces should remain. Now that they are all mingling together and not lost in the closet, look for a connection, a narrative through-line. In other words, is there something that the pieces you love have in common? Bright colors, marabou trim? Sumptuous fabrics and shades of gray? Sometimes seeing all of one’s favorites grouped together can be a bit of a shock. One may think of herself as a Jackie Bouvier type, but her most beloved pieces are more like burlesque star Tempest storm. What to do?

First, congratulations—your soul has spoken! A discovery has been made. look closely at the pieces. What do they have in common? Is it a shared silhouette? Are they waist enhancing or perhaps light and ethereal? What the pieces have in common can be thought of as their form. If, for instance, favored pieces tend toward the ethereal, it does not mean that dressing head-to-toe like a fairy is a good idea. It means that incorporating pieces light of form will ensure that you are happy when the closet door opens.”

Items so expensive you feel horribly guilty getting rid of them:

“Mistakes were made; find the unloved items a new home. These items are especially pernicious because one remembers the moment of plunking down all that cash or credit every time one glances at them. This can often lead to face-flushing, feelings of unhappiness, and self—recrimination. Since you never wear them, they should be in good condition and therefore avoid the Throw-Out Pile. As they hit the Give-Away Pile, whisper a solemn oath to not make such silly purchases again. Repeat: Cheap Is Chic, Cheap Is Chic, Cheap Is Chic. There, all better. If you feel you must recoup something and the item retains its value, there are always consignment shops, but eBay is much more au courant.”

the start of what to do with “the rest” of the closet

Items that don’t fit:

“This is a broad category that ranges from the aforementioned velvet jeans to items that do indeed fit, just not well. There is no reason to have something taking up space in your closet that does not make you feel good. These items must go. Perhaps you like to torture yourself by trying on some jeans from a few years ago to see if you can button them. Clothes do not exist to humiliate their owners. Please do not force garments into performing psychological tasks for which they were not designed. Furthermore, please be kind to yourself. They don’t fit. Toss ’em. “

“Ultimately the following process should allow you to divide your closet into four distinct piles. Choosing what stays and what goes can be intimidating, but we have nothing to fear if we listen to Søren. He counsels that the unmediated choice is the only choice one will never regret. That means no agonizing over whether or not to keep the jumpsuit. If you have to ask, the answer is: Throw it away. If, however, the item causes heart palpitations of happiness, it goes in pile number one:

1. The Soul-Stirring Pile. Keep in mind that this pile is not just for fantastic items; that flattering cotton tank you love goes in this pile, too.

2. If a beloved garment needs some attention, put it in The Repair Pile. You now have exactly five days to go to the dry cleaner or tailor. Do not allow items to languish. If this is a temptation, perhaps the item is not important enough to fix.

3. The Give-Away and The Throw-Out Piles are where things often get hairy, as in filled with dangers or difficulties.

4. Let’s look at what remains in the common closet after the Soul Stirrers and Repairs have been set aside, and decide what to do about what’s left on the rack”

“Closets are often where we hide things: skeletons, forbidden loves, terrible birthday gifts we couldn’t return. It is for this reason that deciding what to wear while staring into those murky depths can be not just daunting, but emotionally exhausting as well. That lace bed-jacket bought at the antique store in Vermont? Those velvet jeans that were already too small the day you picked them out? That cocktail dress purchased especially for the party that was an absolute dud? You remember them all. How could you forget? They stare back at you every time you open your closet door. The time has come to wipe the slate clean and cleanse your sartorial palate.”