How To Buy Clothes You’ll Wear a 100 Times (or More)

Clothing hanging neatly in a closet.
Photo by jordi pujadas on Unsplash

The most sustainable clothes you can buy are ones that you’ll wear at least 100 times. Their eco-consciousness is second only to hand-me-downs, vintage, or thrift. Even “sustainable” brands become resource drains if you buy a different sweatshirt for every day of the month.

We collectively have a shopping problem. According to internal research at Rent the Runway, the average American buys 68 pieces of clothing a year, and 80% of that is seldom worn.

Even donating those clothes isn’t a fix. I’ve seen many thrift stores that are jam-packed with rows and rows of clothing like giant warehouses. The fact that 85% of all textiles are not recycled in the U.S. does not surprise me.

Personally, I used to buy piles of cheap clothes on a whim — some laid back and ’70s inspired, some gaudy and camp — and nothing stayed with me for over a year. It was all just an experiment. Eventually, I moved this creative expression to a digital space, and shifted my mindset about buying clothes.

I’m no longer a casual shopper. When I go to a store, I don’t get distracted by a dress that says “bohemian care-free” or a pair of heels that remind me of summer. I’m the bane of marketers everywhere because I already have a plan.

And below is an outline of that plan for making slow and intentional clothing purchases.

1. First, Declutter

Buying more intentionally involves taking an inventory of your current wardrobe. In order to understand what works for you, it’s critical to understand what doesn’t work for you.

For two years straight, I decluttered an item a day, and much of that was from my wardrobe. It wasn’t until about a year into the “challenge” that I started buying clothes again.

Noticeable patterns emerged from the clothes I decided to keep. By decluttering my sweaters, I learned that I only liked ones with a neckline above a crew. By decluttering my jeans, I realized I only felt comfortable with a high-rise waist.

Slowly, I figured out my likes and dislikes — all through first decluttering what I already owned.

2. Picture It, Then Sit On It

While decluttering, you’ll slowly realize some gaps in your wardrobe. It could be one item that could pull together several other items. Or it could be a functional piece that you’re missing for specific occasions.

For example, once I’d significantly decluttered, I realized I had two heavy coats that fit the very far ends of the dress code spectrum: a fancy wool coat I’d wear to ballet and an athletic North Face I’d wear to the grocery store. I had nothing in between.

First, I pictured a coat that I could wear to dinner on a snowy night in Chicago. I started my search online and scrolled through various retailers in order to narrow down the style. I also followed fashion YouTubers so I could get a sense of how different coats would pair with other items.

I mulled over an interesting style with a neutral color that I’d feel like myself in — nothing more, nothing less. I pondered what kind of coat could be effortlessly slipped into circulation with the rest of my wardrobe.

It was at least two months from the time I first considered that missing piece in my wardrobe to the time I hit “purchase.”

3. Go to the Physical Store

If possible, go to a physical store, especially when you’re first beginning to shop intentionally. Otherwise, make sure the online store has a good return policy, and have a mindset that you’ll most likely use it.

I say this because it’s important to get exactly what you want. If you go to the physical store, you can try on ten different pairs of jeans and compare them against each other to get the best possible pair for you.

If you order online, you might be tempted to keep something that’s not 100% perfect because it’s “good enough” and you already have it in your possession.

4. Pass Up the Sales Rack

I used to walk into a store and beeline to the sales rack. I’d buy things only because “it’s a good deal.” I’d make so many compromises just to save a few dollars.

Now I spend more money if needed to get exactly what I want. For example, I’m willing to spend $300 on the perfect coat with cross-functional use instead of $100 on three coats each that are only 80% right for me.

When I spend more on the right piece, I look at it as saving 100% of the cost of a so-so item. And when I have exactly what I want, I become less inclined to keep searching for and buying more to fill in the gaps.

It may seem a little counterintuitive, but this is how spending more on one item might actually help you save money in the long run. That being said, if the thing you want goes on sale, then buy it. It’s a win-win as long as the “sale” part isn’t the driving factor of your buying decision.

5. Dressing Room Meditations

I spend a lot of time in dressing rooms meditating over potential wardrobe items. I could try on clothes for two hours straight and still not buy a single thing.

Here are the three factors I’m considering while in the dressing room (or at home if I’ve purchased online):

Fit and Comfort

Can I move in this without restriction? Would this still be comfortable after having a meal? Is the fabric scratchy? Is the cut flattering to me? Could I pick something up off the floor without worry about the neckline (top) or waist (pants)?

Lifestyle and Style

Am I projecting who I want to be onto this item or does it fit who I already am? Is this something I’d realistically wear in my day-to-day life? How often do I go to formal or semi-formal events, and therefore, do I really need another pair of dressy heels?

Wardrobe Match

Sometimes, I go to a store wearing the outfit I had in mind for a certain style so that I can test it out in real-time. Regardless, I’ll ask myself questions such as: would the cut of these jeans work with the shoes and boots I already own? Do I have enough neutral tops to buy these patterned pants? Could this sweater easily be dressed down or up based on my accessories?

In short, I spend a lot of extra time with something before I take it to the cash register.

6. Keep the Receipt

My final step in purchasing is hanging on to the receipt. Once I get home, I try it on with other items in my closet to double down on making sure it’s the perfect match.

I might let it sit or hang with the tags still on for a few days. Because of this and all the steps outlined above, I now rarely have buyer’s regret. Even better, I’ve bought several (high quality) items that I’ve worn to the point of actual wear; which, in short, means I’ve successfully bought something I wore over and over again.

Final Thoughts

In conclusion, I’ll leave you with this: you should buy sustainably by buying less. And the way to buy less is by buying more intentionally.

After all, you only need so many clothes once you have the right ones. And investing time and energy into each of your purchases is entirely worth it — both for your own pocket and for the environment.



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