Declutter With Confidence Using This Professional Stylist’s Closet Cleanout Checklist

What’s the easiest target when decluttering fever hits you? The closet, of course. It’s probably overflowing with clothes you haven’t worn since college or things you’re not sure why you even bought in the first place. And sure, there are plenty of cliches out there about when to get rid of clothes. But those tired rules – donate anything you haven’t worn in a year, for instance – don’t account for a lot of factors, and this one size fits all approach often doesn’t, well, fit.

Plus, sometimes it’s not as simple as a quick yes/no sort of the closet. There’s so much baggage with our clothes that it can be nearly impossible to let go of some things. As a result we can end up with a closet so packed with stuff we don’t wear that we end up feeling like we have nothing to wear.

Wouldn’t it be nice if there was a checklist to help when it’s time to clean out the closet?

The super savvy and incredibly understanding personal stylist Laurel Kinney – who helps people declutter their closets for a living – was kind enough to offer just such a tool for those of us who can use a little professional help.

“A lot of people look at style from the fashion side and staying current on trends,” Laurel says. “But I like to help people look at it from a self-reflective vantage point so they can find their own personal style and align their personality with their clothes.”

Her process includes what she calls a closet sort, where “we are going through and making sure what’s in your closet is aligned with your personality,” she explains. “Does it physically fit your body and flatter in a way that makes you feel confident? Are the clothes appropriate for your lifestyle and settings you find yourself in? Do you feel like you have enough options that can me mixed and matched easily?”

Then on the emotional level “it’s really about parsing what looks and feels good outside of what you’re emotionally attached to,” Laurel says. It’s “looking at your clothes objectively and trying to separate your emotional reaction to certain objects as touchstones of your memories… some people are just more sentimental than others and some have a hard time bringing things into their life if they aren’t meaningful. [And] especially if you don’t have a lot of money to spend on clothes it’s a function of ‘you have to keep them as long as possible.’ Then inevitably as you’re wearing things your memories pile up and the clothes becomes signifiers of places you’ve gone and compliments you’ve received.” No wonder it’s so hard to start tossing!

If you’re not in a place to hire someone like Laurel at the moment, you can still learn from her process. It helps if you can do this with a friend (a brutally honest one), a style buddy who’s also going through the process, Laurel says. “Tell each other your goal and be accountable,” she says, and “bounce questionable items off them.”

“If you can look at something objectively you can say ‘something isn’t right here.’ The sweater fits but maybe it’s a little long and doesn’t show your waist so you feel a little frumpy. Or maybe the jeans fit well in the thighs but there’s a big gap at waist and they slide down after a few hours. If your pieces are still in good quality but they just don’t fit right, collect all of those and bring them to a tailor and have them tell you if they can be adjusted. If you have pants with a wide waist, that’s an easy fix; [so is] hemming pants. You can also hem, shirts, skirts, dresses … and people forget sleeves can be taken up. You can change things drastically just by making them fit your proportion better.

“Think about how your clothes fit throughout day – maybe they look fine first thing, but throughout the day they sag or become uncomfortable. Or if your clothes are making you fidget that’s going to affect your confidence level and how people see you.”

“Get a friend. Do a little pre-work, coming up with a few words that resonate for you. [Some examples for Laurel’s clients are boho professional, modern feminine, and nature punk.] Being able to hold it up and say ‘does it say or not say such and such?’ can make it easier to objectify it. It’s easier to have the clothes be wrong because they don’t align with a word. Just because your sister gave it to you doesn’t mean it’s saying the right things about you.”

“How is the quality, does it look like you’ve had it a long time in a good way or just kind of tired? Maybe they’re not as shiny and clean anymore. If that’s happening to your clothes you don’t necessarily have to give them away, you can downgrade to clothes you lounge in instead, to make it easier on yourself. And [if it’s too worn or stained to donate] you have to ask: why is it not good enough for someone else but it is for you?”

“It’s important to look at the versatility of each item. Are you wearing it with lots of items, can you dress it up or down? Or is it a one note thing you only wear every so often? Does it take you forever to figure out how to wear it?”

Laurel recommends a purgatory pile for the clothes that don’t make the cut but you can’t quite give up on yet. “Take out stuff that you’re not sure about and put it aside and see how getting dressed with what’s left for two or three weeks feels,” she says. “And if your style becomes more cohesive, it will be easier to get rid of those things.”

What about the things you love too much to lose? She gets it. “I have a collection of my mom’s old Willie Nelson T-shirts,” Laurel says. “I’ve seen people frame old T-shirts.” If it doesn’t break your heart too much you can recycle anything still absorbent as cleaning rags (that’s what I did with all my old powerlifting shirts I was incredibly emotionally attached to). Fancy dresses can be donated to a place “that will use them in a way to make you feel better about the piece having a second life,” she says. One of my favorite things is to stuff a dog bed like Molly Mutt with my old too-worn-to-donate clothes.

And if you don’t have a plan in place (or deep enough pockets) to replace everything at once you can totally do it by section, Laurel says. You can break it down into bite size chunks, she says, starting with jeans, for example. When I went through my own closet sort I focused only on winter clothes. And now that I’m equipped with this checklist I’m ready to tackle warm-weather clothes next!