I find it really hard to find good, used clothing for boys past a certain age. I know boys can be harder on their clothes than girls... and I also think that parents with boys find that doing hand me downs is a little eaiser than reselling or donating boys clothing because the boys they hand them down to don't tend to be quite as picky nor as concerned to be wearing current styles as some girls are. Not always, but to a degree anyway.
So, I figured I'd share my frugal and organizing tips about clothes for my son.
I do check out the Goodwill, Salvation Army and consignment stores for boys clothes - I just don't usually have very much luck. I also browse a bit at garage sales, but they seem to even have less.
When we go clothes shopping (which isn't very often). I usually buy an outfit or two that fits him right now. But then I also hit the sale and clearance racks and pick up more clothing items in sizes 2-3 sizes bigger than he is currently in. Those clothes go into one of two (or three) bins in the closet that hold clothes that are either out-of-season or too big.
I keep an eye on the sales and if I see a great sale, but we don't need anything specific - I might still go pick up a pair of jeans, shirt, jacket, etc and throw it into those bins.
When he starts going through a growth spurt... I start going through the clothes as I pull them out of the dryer. Clothes that are outgrown, but still wearable, go into a tote I keep in the laundry room. When he needs more jeans or shirts, our first place to go look is in the closet.
Three to four times a year, I empty his dresser completely. Clothes that fit and are in-season get pulled out of the closet. Clothes that are too small get thrown into the bin in the laundry room. Clothes that are out-of-season join the clothes that are too big still and get tossed back into the closet until we repeat.
When the bin in the laundry room is full, I either take the clothes to someone for hand me downs.... or if I don't have someone around who can use them, I end up either donating them to someone on freecycle or taking them to Goodwill and donating them. The first is more convenient - because the people picking them up comes to me to get them when it's convenient for me - but isn't tax deductible. Goodwill requires making the trip, getting a receipt and documenting stuff for taxes to deduct the donations.
We go clothes shopping at the regular stores when we really, really need something specific that didn't manage to get picked up on sale prior to needing it. We also get a complete outfit, brand new, around Christmas and Birthdays. Birthday clothes just land in the dresser without much fan-fare. Christmas clothes get thrown into one large gift bag and the youngest looks at it and goes - oh, yeah... that's the clothes bag - sigh. The eldest still gets one (at 24) even though it's usually just a couple of items - but LOVES it to death. The key goodie is usually the new package of socks.
The one other time we do a LOT of clothes shopping is when Iowa has their tax-free weekend in August before school starts. We usually make a trip of it and spend the day shopping for the school supplies we need and some clothes to make those first few days of school just a little more special. Not only are we not paying 6% tax on the clothes, but most of the stores in my area do BIG discounts and special sales. I find that the vast majority of my purchases is at least 40-60% off the normal price on that weekend. We hit two or three of our favorite stores and when we get done we often go out for dinner together as a family to make it a little bit of a holiday.
I find that these tactics work really well for buying clothes inexpensively because I can buy then when they are on sale or especially on seasonal clearance, as well as making the managing of those clothes and having them able to be gotten to easily pretty convenient. The clothes are just there and available, when I need them and don't seem to get in the way, when I don't. Occasionally, "a" will find something 'amazing' in the too big pile and insist on wearing it... which is just kind-a cute in the end.