“With these regrets came the understanding there are certain things you should always hold onto, even if they have fallen out of style.”
I like to think of myself as the queen of closet clean-outs. Every six months, I touch every piece of clothing I own and decide whether or not it is still worth keeping. I time the clean-out with the changing of the seasons, as I am putting away my fall/winter items into storage and bringing out my spring/summer wardrobe or vice-versa. I have found it to be a good way to remind myself of the items I loved enough to store in the off season. It also scratches my shopping itch without spending a dime.
While not quite a minimalist, I do not like keeping things around that do not add value. I have a set rule for my closet: if I am out of hangers, I have to get rid of something before I can bring anything else in, including gifted items. It has kept Chaos from the door for a decade and a half.
If you have never attempted an organized closet clean-out, I cannot recommend closet them enough. I have helped a number of friends when clothing ownership became overwhelming instead of exciting. When it comes to daily dressing, a regular clean-out makes everything simpler. The ability to easily find what you want to wear allows you to breathe. I have found it to be one of the easiest ways for me to remove stress from my life.
However, having done this since my college years, I have also made huge mistakes. Mistakes like getting rid of a piece I really loved or donating an item no longer in fashion only to find with the ever-changing and quixotic tides of style, it was right back in vogue a few years later. While few and far between, I still think of them when I do my bi-annual wardrobe ablution.
“If you love it and you wear it, but there are holes everywhere and you’re afraid it will start showing some bits of you that are meant for private consumption only, then, girl, let it go.”
With these regrets came the understanding there are certain things you should always hold onto, even if they have fallen out of style. And I am not the only one who believes this. I read a comment on a runway video a few years ago which stuck with me. She wrote, “I have held onto a cropped, double-breasted herringbone blazer for thirteen years, waiting for it to come back into style. This is my year.” I am not going to lie - I would have gotten rid of that blazer long before she had. But, it was a piece she really loved and believed in. And now she has the double joy of wearing it and having been right to keep it for so long.
When putting on our closet clean-out hat (see what I did there?), keep these three things top of mind:
1) do you love it?
2) do you wear it?
3) does it still have life left in it?
If your response is “yes” to all three of these, then the answer is simple: keep it. If you love it and you wear it, but there are holes everywhere and you’re afraid it will start showing some bits of you that are meant for private consumption only, then, girl, let it go.
If you love it and it still has life left in it but you’re no longer wearing it because your lifestyle or trends have changed, run it through the list below before placing it in the “donate” pile. You’ll thank me later.
“Keep the things you love, and do not let anyone tell you to get rid of them - especially me.”
Six Items You Should Never Get Rid Of:
DENIM
Jeans have been around for 150 years, and denim was created over 300 years ago. Yes, you read that correctly. Sure jeans looked different in 1876 than in 1976 and now, but the usefulness of a sturdy, navy blue cotton fabric transcends time.
The denim category is broad. It includes dresses, skirts, shorts, and jackets. As long as you love it and it has life left in it, hold onto good denim. Vintage denim always has cache in the fashion world, and the colors and fabric are classic enough to cycle back into style regularly. It is difficult enough to find jeans you feel good in. Don’t make it even harder by throwing your best ones away.
Hold onto your denim items, and enjoy them for decades to come.
LEATHER GOODS
This category is where I have had my greatest regrets and my greatest triumphs. When tall boots became taboo eight years ago, I wore two pairs regularly. I have weirdly skinny calves, so finding boots with a narrow shaft has always been a headache. Instead of tossing them when they fell out of fashion, I gave them a good oiling and placed them out of the way in a top shelf, ready for the day they will be brought back out into the light.
The same is true for belts, shoes and bags. If they are made from high-quality leather, they should naturally have a long-life, and leather accessories are regularly cycling through trends, so the likelihood you will be able to wear them again is high. My mother taught me this lesson in high school when I purchased a belt with double grommets, thinking I was incredibly edgy and avant-garde, until she told me she had the exact same belt when she was a teenager in the ‘70s.
The only time I will give up a leather item is when shoes have become worn beyond repair or when belts become too small… because they, uhhh, shrank in the wash….
cough Let’s move on.
GOOD JEWELRY
Jewelry trends tend to be longer because the cost of high-quality jewelry is significant, and people want to get use out of their best pieces. If you own good quality jewelry made from - or at least plated-with - precious metals, hang on to them. Well-made jewelry will always have a place in fashion, and the variety of ways you can use jewelry is nearly endless, even for an old hat pin. Get creative with those old pieces and turn them into brooches, bracelets, or hair accessories.
When my grandmother passed away, my sister and I went through her jewelry box and kept what struck our fancy. I have two brooches from her, both of which I added to my wedding bouquet to keep her memory close on that special day. After the wedding, I put one on the lapel of my black wool coat, and there it still sits. Whether it’s for future family mementos or because you can find new and interesting ways to wear them, jewelry has been a sign of taste and an outlet for personal style for thousands of years and won’t stop being so in our lifetime.
STRIPES
This one might surprise you: keep your stripes. Stripes are one of the oldest patterns in human clothing. Even ancient Egyptian paintings show striped linen garments. Throughout the centuries, various versions have been used to mark religious affiliation, class, incarceration and military service.
And while we see less of those specific uses today, stripes remain relevant and widely utilized in fashion. From subtle pinstripes to bold Breton stripes (my personal favorite), they are a classic way to add dimension to an outfit without becoming dated. Don’t pull them out of your closet without pausing to really think. Perhaps you are not a stripe person; perhaps it’s a very loud or unusual stripe you have never felt comfortable in, in which case I understand adding it to the donation pile. Hold on to all your other stripes, and enjoy bringing them out for a weekend getaway, a bbq, at the lake, or on a Tuesday.
HIGH QUALITY OUTERWEAR
Outerwear, especially high quality outerwear, should stay in your closet for a very long time. If you are replacing your coat every two years, it is time to rethink your outerwear buying strategy, but this is a topic for another day.
High quality outerwear should last five or more years of regular wear and, when buttons pop off or the lining starts to tear, a tailor can give them new life and add another five to ten years to their life. Outerwear tends to be made of heavier duty fabrics like wool or twill, and therefore will naturally be more durable than, say, a cotton shirt. If you have a coat that is looking a little sad, with loose buttons and a few stains, take it to a good dry cleaner and tailor and be amazed at how perky it looks when you get it back. You’ll fall back in love with it instead of adding it to the donation pile. Look for coats with full linings and the highest concentration of natural fibers you can afford, such as wool, cashmere, or alpaca.
One habit I have gotten into to keep my outerwear looking good longer is, as the weather turns warmer, I take all of my coats into the cleaners before storing them away for the season. This removes any stains from the fabrics before they really set in while also increasing the pleasure you get when you take them all back out again in the fall. Plus, I never have time to dry clean them during the winter, so it is a good way to invest a small amount to elongate a coat’s utility.
YOUR FAVORITE ANYTHING
If you are anything like me, you remember a favorite outfit from high shcool or college or your early twenties that really meant something to you. Perhaps it was what you wore on your first date with your now-husband (for me it was dark, flare jeans and a black peplum top with a small geometric pattern on it), or the outfit you wore on your first day at a new job (gray Nordstrom skirt suit with reverse box-pleats in the back). Perhaps it is as simple as a jersey dress you have always felt especially lovely in.
Whatever it is, hold onto it. It doesn’t take up much space in the scheme of things, and life is short. No one is thinking about you as much as you think they are, which means no one is worrying too much about whether your favorite top has fallen out of style. Even if you are in a season where you do not have as many opportunities to wear it, do not get rid of it just yet.
I have a sleeveless tuxedo dress in mulberry I purchased the year before I left corporate life. I got the chance to wear it twice, and now it hangs in my closet, waiting for its next outing. I refuse to give it up. It is incredibly well-made, a classic silhouette, and I feel amazing in it.
Keep the things you love, and do not let anyone tell you to get rid of them - especially me.
Now tell me, what did I miss?

