New Wardrobe, New You: What to Ask Yourself While Cleaning Out (& Revamping) Your Closet

I’m a stress cleaner—as in, I tend to clean and organize things when I’m overwhelmed or feeling down. And if there’s one thing I’ve learned from my emotional clean-out sessions, it’s that the sometimes the most satisfying thing on the planet is cleaning out your closet—even if it’s hard for you to part with some of your old favorite clothes.

Decluttering your wardrobe doesn’t just help you be more organized, it can help you be more stylish, too—paring down your closet makes it so that you’re left with only the clothes you love and room to add in new pieces that you want. And sometimes a streamlined new wardrobe is the refresh you need to feel like a totally new person.

If you’re about to embark on a full-on closet decluttering session, ask yourself these questions—it’ll help you get a better perspective on what you actually want to keep and what you should get rid of.

Holding on to things that don’t fit (it doesn’t matter if they’re too big or too small), especially if you’re hoping to fit back into them someday, isn’t doing you any favors, and could be really hurting your self-image and confidence. So, before you consider anything else about a piece of clothing, ask yourself if it fits the body that you have now—not the body you used to have or hope to have some day, because the body you have now deserves cute clothes that actually fit it. If it doesn’t fit, let it go.

Just because you like it doesn’t mean you actually wear it, so if you haven’t worn it in months and you can’t think of when you’ll wear it next, you’re just holding on to something cute that serves you no purpose. On the other hand, sometimes going through your clothes will help you find a piece you loved but forgot you had—now’s your chance to start incorporating it back into your wardrobe. Otherwise, anything that you rarely or never wear and can’t foresee donning in the future should go.

If you’re only going to wear it once or twice (excluding certain pieces, like formalwear that you’d wear to a wedding or special occasion, of course), it’s probably not an item of clothing you actually need to hold onto. Unless you’re going to get a decent amount of wear out of it, you can put it in the “go” pile.

Anything that needs to be patched, stitched or otherwise repaired that you haven’t actually gotten around to fixing in who knows how long definitely needs to go. If you love it enough to fix it or have someone else fix it for you, hold onto it—but give yourself a short deadline for getting it done. Same with anything that needs to be tailored—if it’s just hanging in your closet because it doesn’t totally fit you right but you haven’t bothered to take it to a tailor and you know you probably won’t, donate it.

You might have a particular item that you love and would wear, but you don’t have the right pieces to pair it with so that you can wear it. That’s when it’s time to decide whether you love it enough to buy items that will compliment it, or to pass on it entirely. If you can’t even think of what you’d pair it with, it just might not work for your wardrobe.

That dry clean-only sweater that you never wear because you never remember to actually take it to the dry cleaners? Probably time to say goodbye to it. Any items that don’t actually fit into your lifestyle and that you know you don’t have time to follow the care instructions for are not a good fit for you.

This is the most important question to ask yourself when you’re deciding whether or not to keep an item of clothing—if wearing it doesn’t make you feel good about yourself, it’s time to let it go. Even if you’ve got a sentimental attachment to it, there’s no room in your new wardrobe for old pieces that don’t make you feel happy and confident.

The best time to figure out what new pieces you actually want to invest in is when you’ve got a clear picture of everything you have. Once you know what you’re keeping, think about the items that you want but are missing and what you’d pair them with, then jot those items down so you know what to look for on your next shopping endeavor. That way, your new wardrobe will be exactly what you want it to be (and your wallet will thank you for not just buying whatever cute things you see—after all, that’s probably how you got to this point in the first place!).