If you’re serious about clearing out closet clutter, this is your challenge: Pick something at random and wear it tomorrow.

If you cannot wear it tomorrow, then it needs to go. No arguments. It’s out. If you can’t find a way to wear it alone, layer it under something or drape it over something, then what the heck is it doing in your closet?

Once you wear something successfully, it’s safe for six months.

Aha, you caught that word “successfully,” didn’t you? Thank goodness you were paying attention. If during the day, you notice, “Oh yeah, this is why I never wear these pants/skirt/blouse, it’s because they ride up … there’s a hole by the knee … there’s a stain on the sleeve … it’s itchy,” it’s a goner.

If it’s damaged or irksome to you, it will be noticed and irritating to someone else, so put this directly in the trash, not the charity box.

OK, so you really like that jacket, but no one at work wears a jacket, so you can’t wear it. WRONG. Dressing up is fun. When people ask me where I’m going, I just smile and tell them that I’m already there. Do it often enough and people will stop asking. Maybe they’ll be inspired to dress up, too.

For everything you can’t wear that’s in good condition: charity heap.

Here’s the exception: You love it. You really, really love it. And you’ll wear it when the time is right for you, then you can keep it. I’ll argue that the time is almost always right, but I typically walk that high-heeled-boots-with-polka-dot-hosiery line alone.

Now that you have the gist of the challenge, let’s spell out the fine print.

– Anything in the laundry basket right now should be the last thing you wear. You know what clothes you like, what about everything else? To separate what you have worn and haven’t worn, start by putting a piece of masking tape in a conspicuous place on everything. Take it off when you wear it and take a look at what’s left at the end of the month.

– Shoes are included. You have a month to wear the everyday shoes and you have three months to wear all the special occasion shoes. Yes, that means you should find a special occasion. I fully understand that you need a lot of shoes. I know what the lack of proper footwear can do to sabotage the perfect outfit. But if you’ve got ’em, wear ’em. The only shoes you absolutely don’t need are damaged shoes, shoes that you can’t even look at without wincing in pain or shoes that are severely outdated.

– You do not get a free pass on formal attire. If you own more than a dozen special occasion dresses and you go to fewer than two special occasion events a year, let’s reassess. Ask yourself if you had a dinner party, wedding reception, gala or festive ball to attend this weekend, would you wear that dress or pantsuit or would you go shopping? It’s OK to have two or three emergency dresses, but 15 is ridiculous if you’re the once-in-a-blue-moon partygoer. Pick the most versatile and give the rest away so that someone else shopping for some special occasion will see your cast-off with fresh, appreciative eyes.

– Anything outdated or ill-fitting should go immediately. Face it, you are not really going to have it altered … ever. So toss it.

– Don’t forget the sock and underwear drawer. These things need to be weeded out, too. It’s hard to replace a complete wardrobe of bras that each cost as much as a wool sweater, but even small amounts of change are good. Besides, a bra with worn elastic or an improper fit doesn’t do anyone any good. Forget about how cute it is and ask yourself if it makes you look good in a T-shirt.

– Conversely, just because you wear something all the time, doesn’t make it great. If you love it so much that it’s the first thing you wear from the laundry, then give it a rest for a while. See if you can wear everything else first. Then go back to it. I have a favorite gray skirt that skims my hips and flutters at the knee when I walk. It’s as comfortable as pajamas, but looks as cool as an Audrey Hepburn pencil skirt. I force myself to moderate my use of it because I don’t want to wear it out. And I don’t want to diminish its appeal. If people see you in something cool all the time, it is no longer cool. It’s that skirt you wear all the ding-darn time. Take note, especially if something is really distinctive. And the next time you wear it, don’t wear it with the same thing you always wear it with. This is a challenge, too. Freshen up that look. This is a really good fashion exercise to shake up ho-hum fashion choices.

Most everything you own should be mix-and-matchable. So mix it up!

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