I love cleaning out my closet. It gives me an excuse to fill it with new things, and an opportunity to give my clothes to people who need them. Bonus – donations of clothing and other goods are tax deductible!

I have a habit of likening my clothes to investments. I compare how much the item cost me to how often I wore it, how often it drew compliments, how comfortable it was, etc. Admittedly, there have been some really bad investments over the years. There was the pair of $15 cotton gaucho pants that I wore twice before realizing that some trends are just a bad idea. There was the poorly-constructed knit sweater that completely unraveled Weezer-style when a door hook decided to pull a thread as I walked away. There was an overambitious pair of 5-inch pumps that, even after months of practice, made me walk like Bambi out of the womb.

On the other hand, there are some items that truly stand the test of time. By now, some of these items have probably cost me less per use than my TGIF vanilla latte. And when your clothes accumulate that kind of mileage, you’re bound to have memories attached. I can say with confidence that few items have gathered the mileage and memories of my Little Black Dress (LBD).

In December 2008, I was at Target (or as I also like to call it, Heaven) picking up last-minute items for a Holiday trip to Chicago. It had been nearly 10 years since my last white Christmas and I had yet to find a Holiday dress that could withstand the Midwest chill. I had all but resigned to wearing a nice, but entirely unglamorous skirt-sweater combo when the dress caught my eye on the way to Cosmetics.

The dress was the last one on the rack and just my size. It was strapless with a velvety crescent moon print. The figure-flattering empire waist would hide the inevitable Holiday food bump. The Victorian-esque ruffle and three crescent moon buttons on the chest gave it added pizzazz. Most importantly, it was sturdy and warm – a perfect Holiday dress! It was $20 out of my price range; but when God sends you a sign like that, you don’t ask questions.

After that Holiday dinner, the dress made regular appearances at parties (including my 23rd birthday party) and the occasional fancy dinner. The hemline was long enough that, with a cardigan to cover, the dress was still appropriate for the office or similarly conservative venues. Versatility is key when choosing your wardrobe staples. When my other outfits just didn’t seem right for the occasion, I knew my LBD wouldn’t fail me.

On Halloween 2010, I found myself without a costume with just hours to the evening festivities. I wore my LBD and apparently the last available witch hat in West Los Angeles. The costume was effective – my bewitching powers transformed the guy I was dating into my boyfriend well before midnight.

When my beloved uncle finally passed away five days before Christmas after a painful battle to cancer, the last thing on my mind was what I was going to wear to his final ceremonies. And between chauffeuring family members from out of town and organizing everything, there wouldn’t have been time to pick up something new, anyway. I wore my LBD to the wake. It was strange to think that just a few years earlier, I was in this dress sitting next to him at Midnight Mass singing Christmas carols. Yet the memories attached to the dress somehow made it easier to celebrate his life.

As you can imagine, it took a while before I could wear that dress again. Even now it’s not in the first string of outfit choices. The black has faded a bit from years of washing. I’ve purchased new outfits that I wear more frequently, including new black dresses and trendier, seasonal apparel. Nonetheless, the dress has its place in the foundation of my garment hierarchy. Until the LBD wears out completely, it is likely to remain that way.

Realistically, not every purchase will be like your LBD, or your perfect blue jeans, or your go-to chunky sweater that’s practically a comfort blanket. But it’s a good idea to heavily consider the longevity of your clothes and accessories before you buy them, particularly if you are on a budget. Indulging in the trends is fun and fashionable, and there will always be room in the closet for those purchases. No doubt they are destined for their own compliments and adventures. But it’s the quality, timeless staples that continually prove to be the best investments. The classic, versatile pieces that you can wear year in and year out without completely wearing out will end up costing you very little per use. And if you’re very lucky, as in the case of my LBD, the memories you make in these clothes make them truly priceless.