“Does this shirt make me look fat?” I asked Kris the other day. I was trying on clothes as I packed for our upcoming vacation in France and Italy. I want to limit myself to just four or five shirts for the trip. (Truly light packers would probably only take two shirts.)

“Well,” Kris said. “It’s not that the shirt makes you look fat. It’s just way too big on you. It looks like a tent. Most of your shirts are like that now.”

I laughed because I knew she was right. It’s great that I’ve lost 35 pounds so far this year (with another 15 pounds until I reach my goal), but one side effect is that my clothes don’t fit very well anymore.

I have three lovely cotton t-shirts, for example, that I bought from Costco in March. They’re heathered earth tones, which are perfect for me. (I’m a heathered earth tones kind of guy.) If these shirts still fit, I’d wear them all the time. But they don’t fit anymore. When I wear one, I look like I’m under sail! Ahoy!

The truth is, it’s time for me to buy some new clothes. I’m no longer an extra-large; I’m a medium. So, today I bit the bullet: I went clothes shopping…and not at a thrift store.

Shopping with Confidence
I’ve always purchased my clothes at one of two places: Costco or a thrift store. For years, I took the shotgun approach to clothes shopping. I’d buy a bunch of cheap stuff in the hopes that one or two items would see regular use. This worked — sort of. Using this method did let me find pieces of clothing I’d wear all the time, but it also gave me a closet full of junk.

I recently spent an entire year sorting through my clothes closet. For twelve full months, I noted which shirts I wore. At the end of the project, I purged anything that hadn’t been used. When I shared this story in May, I didn’t really know what lessons to draw from it. But over the past few months, I’ve realized the project taught me a lot, both on a micro level and a macro level.

On the micro level, I discovered that it’s possible to buy good-quality new clothes without worrying I’ll never wear them. The key is to look at what I already wear.

The clothes I kept after my year-long wardrobe project all had similar features. Namely, they were mostly “classic” items that will always be in style. I had a lot of formerly fashionable clothes in my closet (well, as fashionable as I get anyhow), but I rarely wore them. I didn’t wear patterned shirts, either, or clothes with words and logos. I favored plain clothes, especially those in a single solid color. (I like plaids, too, but Kris doesn’t, so I’m trying to keep those to a minimum.)

I also found I tended to like synthetics instead of natural fibers. Heresy, I know, but when I go to my closet, I skip over the clothes with wrinkles. I go for the things I can just pull out and wear.

Understanding these things about me makes a difference in the way I shop for clothes. In fact, this self-awareness made it possible for me to go buy new pants and shirts today without worry that they’ll just end up closet clutter. I shied away from shirts with patterns, sticking to solid colors instead. Because I know how much I’ve worn my $8 pair of zip-off pants over the past five years, I had no qualms spending $65 for a brand-new pair. (Although I’d obviously have preferred to get another pair for $8.)

My wardrobe project has taught me that it’s possible to shop for new clothes wisely. But it taught me something about the Big Picture, as well.

The Clean Slate
Last week, Adam Baker interviewed me for his Sell Your Crap project. After we talked a bit about my clothes purge, he made an interesting observation.

Baker pointed out that what I’d done with my clothes was essentially create a “clean slate” and then gradually add things into my life. He said that most of the time, we have a tendency to try to reduce clutter by taking things away from the entire population of Stuff we own. I guess you could say the usual approach is “subtractive” (we de-clutter by taking stuff away) and my closet project was “additive” (I started with nothing and then added until I reached a pre-determined limit).

Hearing Adam say this produced a big Aha! moment for me.

Most of the time, I’m one of those who uses the subtractive approach to de-clutter. I want to keep taking things out of my life until I somehow reach just the right level of Stuff — whatever that might be. The problem is, I never seem to reach that level.

What if instead I found a way to use the additive approach, but on a large scale? Is there a way to do a complete clean sweep of all my Stuff and then gradually add things back in? What about using this approach with my time?

This reminds me of my Man Room. When we moved into our house six years ago, we had one room downstairs that was essentially unused. We didn’t have any furniture for it. For years, it was just sort of a holding area for the Stuff that didn’t have any other place to live. Last year, we bought some new furniture for the room — but we only bought the essentials. For the past twelve months, I’ve been disciplined about not allowing extra Stuff to creep into my Man Room (or den, if you prefer).

I also think about what I call my Dream Apartment. Despite living in our dream house, I have a fantasy of moving to an apartment or condo in downtown Portland. For the past few months, I’ve been using Evernote to collect things that would go in the Dream Apartment (example). When I imagine the space, it’s very spartan; there’s very little there. Only the necessities.

I told Kris about this the other day, and she just laughed. “You could never do it,” she said. “Look at all the Stuff you have in the house we have. Where would it all live in your Dream Apartment?”

She’s right, of course — Kris Gates is always right — but still…a part of me would love the opportunity to move just so I could start over using the clean slate approach. I’d love to get a new place, and just have it sit empty for a couple of weeks while I get a feel for it. Then I’d add just a few things at a time.

My friend Sparky used to live like that. He owned almost nothing. And while I don’t aspire to his level of non-attachment, I often think about how little he needed to get by. I think about how little I need to take with me when I travel. I wonder what it would be like to start with a clean slate — and keep it clean. Could I do it? I don’t know, but I’d love to try.

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