I've been working towards a more minimalist lifestyle and have been paring back my physical possessions over the past 4 years. I've gone from having a moving truck full of junk to, other than a couple pieces of furniture, to about 7 plastic totes full of stuff. This, of course, is a far cry from when I first moved out of my parents house and I could literally fit everything I owned in a 1988 Honda Civic Hatchback, by myself, in a couple of hours of packing and unpacking. I've been reading about people trying the 100 item challenge: these are folks trying to pare down their physical possessions to 100 items only. Some play loose and fast with the rules, depending upon the situation, but the idea is that you minimize your stuff to "needs" and maybe a few "wants". I've worked through most of my stuff, but haven't really touched my closets. This one is going to hurt. I'm actually relieved, in a way, because over the past few years, I've been tryign to focus on "quality" over "quantity". I've a few pair of leather soled shoes for repairability, I've switched to higher end heavyweight raw denim for durability (8 months on a pair of RRLs. At this point with my last 3 pairs of Levi's, they're not even good for "work jeans" any more they're so destroyed). Trying for more "timeless" pieces vs "fashion" pieces. And yet, I still feel overwhelmed a bit. So, let's say I'm going to narrow my wardrobe down to about 20-25 pieces at most. I'm counting socks (all) as an aggregate of 1, same with underwear and my white undershirts. I'm a firm believer that one can never have too many pairs of clean undies. Start skimping here and it's a quick trip to grody-ville. At the same time, I'd like to use this opportunity to update my wardrobe a little bit and replace some items with higher-quality, more "timeless" pieces that i can comfortably wear into my 40s in Southern California (I'm 36). Let it be known that I'm not a suit guy. Being in Los Angeles, fortunately, I don't have to be. Trying to avoid sounding like fight club, but here we go: pants: 2 pairs of jeans (one for daily work wear (RRL), one for working on the motorcycle, out in the garden (levi's)) 1 pair of khaki's (more of a casual going out alternative to the jeans) 1 pair of slacks (job interview) 1 pair of cords (for the 2 months of cold) Shirts: 3 outer t-shirts (AA ringers, etc) 2 "work" shirts (motorcycle, etc stuff.. old logo'd crap) 3 polos 3 button downs outerwear: 2 sweaters (probably something merino & cotton blend.. doesn't really get all that cold here in LA) 1 hoodie sweatshirt 1 riding jacket (right now, John Varvatos converse) 1 pea coat Shoes: 1 pair black converse high-tops 1 pair work boots (haven't decided yet. After seeing/trying on the Gentleman Traveller's, I actually prefer the Dr. Martens (will probably go with Solovair)) 1 pair black Dr. Martens monkstraps Belts: 1 black 1 brown both casual. 1 reversible (yeah, tacky) dress belt. 1 wallet 1 hat Already at 30 or so pieces.. so I still have some paring down to do. Anyway, I suppose the point of the exercise is, if you had to pare down your clothing down to 20-30 pieces, how would you do it? What would you keep?