For decades, I've been a proponent of habit tracking. Habit tracking sounds and feels nerdy to a lot of folks, so many people avoid it. That's too bad. Habit tracking is a powerful tool that can help you make better decisions about your life.

Let me share an example.

Over at Reaktor, Olof Hoverfält recently published a long piece about why he's tracked every single piece of clothing he's worn for three years.<

Note: This is a substantial re-write of an article I first published more than twelve years ago. (Yikes, I'm old!) I've opted to keep some of the older comments if they had good suggestions.

Earlier this week, I wrote about my quest for quality pajamas. I recently paid $80 to purchase a pair from Filson, a company I trust for well-made goods. It's my hope that these will be the last pair of pajamas that I ever purchase. My goal was to "buy it for life".

This experience reminded me of two other companies that I love for their top-notch stuff.

Yesterday, I spent $80 on a pair of pajama bottoms. (Or, as the company calls them, Alaskan guide lounge bottoms.)

On the one hand, this feels like an insane amount to spend on sleepwear. On the other hand, my last two pairs of pajamas -- both $20 specials from Costco -- have lasted no longer than a year because they've quickly fallen apart. They were cheap garments cheaply made.

Herein lies a question I frequently face: When does it make sense to pay more for quality?

I'm in Florida for ten days to attend a couple of weekend early retirement retreats. At Camp FI, about 50 or 60 people gather for three days of what Mr. Money Mustache calls "crazy rich people talk" -- real estate investing, travel hacking, gift card arbitrage, 70% saving rates, and the rewards of frugality and thrift.

One afternoon, the conversation turned to clothing. Given that so many people in the room had a net worth of more than a million dollars, a surprising number of us still bought our clothes at thrift stores.

https://www.youtube.com/watch?v=QK8mJJJvaes

A couple of years ago, I had a Great Closet Clean-Out. My clothing racks and drawers were overflowing at the time, and some of it still had price tags. Hoping to accomplish that European knack for owning less and looking better, I donated, consigned, and gave away about 75 percent of my wardrobe. Today it's 100 times more functional.

But before we talk about the state of my closet today, here's an idea of where I started…

Three Closets, No Space

When I graduated from college, my first apartment came with three closets -- two in the master bath, and one in the hallway. I easily filled them all. Continue reading...

We have all been there: standing in front of our closet or dresser drawers, looking at the contents, and waiting for something to emerge. That surprising dress or just-so shirt. That pair of pants that fits like it was tailored. That pair of shoes that is the sort of pair of shoes people refer to when they advise their friends to judge others on their shoes.

Once in a while, a surprising, just-so, tailored-seeming, universally impressive article of clothing appears, though rarely of its own volition. The rest of the time we just stare.

Maybe it's time to go shopping.

Ever since I cleaned out my closet, I've gotten more and more ruthless, editing more and adding less.

The result of deleting items from drawers and hangers is two large brown boxes taking up floor space in the closet, overflowing with castaways. The boxes have grown into mountains, and I can't walk to the back of my closet anymore.

My intention was to sell these items, which are the nicer things that I actually like, but don't work for one reason or another. I didn't want to drop them off at the consignment shop because the shop keeps 60% of the profit and only accepts in-season clothing, meaning I'd have to keep some of this Stuff in my closet for almost a year. So I planned to sell it on eBay, thinking I could make some of my money back and maybe sell the out-of-season items.

I spend almost nothing on clothes. According to Mint, I've spent $199.50 to clothe my family of five this year. They say the average U.S. household has spent $1258.62. That's more than six times my spending.

It's been years since I walked into a clothing store, tried on styles I liked and bought myself a new pair of jeans. That doesn't mean I'm content to dress like a slob, or wear the same tried-and-true favorites season after season. I change up my wardrobe every few months with a huge shopping spree — from my friends' closets.

The Clothing Swap

My friends and I hold clothing swaps at least once a season. We all clean out our closets of anything we don't love that's still in good condition. We get together and swap our cast-offs around. I'm a walking advertisement for the aphorism, "One person's trash is another person's treasure." Continue reading...

About a year ago, at the advice of GRS readers, I started an experiment. I took all of the shirts and sweaters from my clothes closet and moved them into our spare room. Whenever I needed something to wear, I checked the clothes closet first. If what I needed wasn't there (as was often the case at first), I went to the spare room to find it. After I'd worn a shirt or sweater once, it was allowed to return to its home in the main clothes closet.

The results of this experiment probably won't be very surprising. After a couple of weeks during which I was reclaiming my favorite shirts, most of the rest remained unused. For an entire year.

On Tuesday, I gritted my teeth, grabbed the 37 shirts and sweaters still left in the spare room, and took them to a local thrift store. Some of the things I donated had never been worn (or had been worn just a couple of times). It hurt to part with those clothes. I probably spent more than $750 to purchase them (remember, I buy a lot of clothes at thrift stores), so in a way it felt like I was throwing away $750.

Moving to the D.C. area after my twins were born, we transformed from a family of three living comfortably, to a family of five struggling to make ends meet on one income. I had to get creative with our family budget, and one of the biggest line items to tackle was clothing. Four years later, I finally have a handle on it. Shopping for clothes for my three kids has been fine-tuned into a system that keeps us humming along season by season. How?

1. I get the best quality I can within my budget.
2. I take good care of what we have (and teach my children to do the same).
3. I resell my kids' clothing in good condition to recoup my costs.

Buy Quality Clothes — For Less

You can save on sturdy kids' clothing — I get great longevity from Lands' End and Gymboree — by only shopping sales and clearance. In her article about the best time to buy almost everything, April mentioned which days are best to shop the clothing stores, but knowing the seasonal clearance schedule is helpful as well. For example, I send my kids to their first month of school in shorts and wait for the jeans/pants/leggings to go on sale in late September and October. Winter coats are on clearance in February; be ready to shop ahead for next year.

You can shop online, but do it wisely. I never shop online without coupon codes, and I always shop through a cashback site like Ebates. Shopping online gives me a larger selection of clearance items than local stores. Additionally, shopping online helps me stick to my list and budget, whereas in a store I am tempted to make impulse buys. Finally, most online retailers allow you to return clothing to the store for free if they don't work out.

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