I am a firm believer in shopping in advance. I mean a season ahead people. I also love freecycle.com and craigslist for stuff. I have an awesome friend who passes down many clothes from her son to my twins. Thank you very much. With 3 year old twins and a 20 month old we will take what ever we can get. Don't be ashamed your kid doesn't have the most in style thing or the newest fahion. Most will just grow out of it ASAP.
Other tips:
I love shopping clearance and with coupons as well. Target has awesome clearance and my kids super cute Cargo jackets were $4 last year. Yes, it takes a little planning but why not. All those stores with great clearance sales like Carters, Macy's, Osh Kosh( got sandals for $5 each in August) Old Navy, and Kohls, are great places to help out a hand me down wardrobe or spruce up the closet,
I love to check with the mommy groups, many have trading parties and you can get some great stuff for free and have a fun night out. Also the great used sales that are popping up now are so great. or even Threadup.com
Shop the big sales: Did you get the important stuff on black friday or when Old Navy had %75 off all coats last week?? Also use those coupons in the adds. I got jammies for all the boys when I realized they are almot a 4t now and my one twin could not fit his feet into his footie pj's. JCPenny, $10 off coupon adn early bird special and I was out of there for $10 for 3 pairs of jammies.
Lastly:
Shop the deal sites, I got a $10 for $20 old Navy coupon and then went on Black friday and got fleece for everyone including daddy for $10. Yeay!!
You have to just have fun, keep a sharp eye and go for it!! Same goes for me and the hubbs too!