I know every family is different, but here's my advice from the trenches on how to make back-to-school clothes shopping both easy and fun for your family... Be the coach! Yep, that's my advice. Be the coach.
I watched a parenting video years ago, and the educator said that there comes a time when your role as parent changes: you go from being the "parent" to the "coach." At the time, I didn't know what he was talking about: I'll always be the parent I thought. But now as my daughter has reached the ripe old age of 8 and a half, I'm starting to understand, and our clothes shopping trip to Target turned out to be a great experiment. As a parent, there are certain things I need to make sure happen, one being that my daughter gets to bed at a reasonable hour with brushed teeth. Another is that at least a tiny bit of nutrition enters her body (this is actually hard with a very picky eater). I also need to make sure she is kind to herself and to others. But now we enter the grey area, the places where I could exert control and have it be my way, or I could back off. Through trial and error, I've found that the less I involve myself in her "business," the more successful I am. It's the push-pull thing. The less I push, the less she pulls. So this year, I said I was leaving clothes shopping up to her. My rule to myself was that if she asks me my opinion I'd give it, but otherwise, I would let her be the boss. She took the job very seriously. If you read my last post, you saw that she's no longer into rainbows, butterflies, or fairies. In fact, a new sophistication has emerged. Pink, purple, and sparkles are banished. Now it's cool jeans (see below) with stylish blouses, and her first maxi skirt with a belted shirt (all her own idea). When she asked me my opinion, I gave it, but otherwise, I hung back. It was actually way less stressful for me.
So my easy hack for back-to-school clothes shopping is to let your kids take the lead. (I know if you have a two-year-old, your main concern is just avoiding the meltdown in the toilet paper aisle.) But given how happy Lainey and I both were during this trip, I wish I had understood about being the "coach" a little earlier. Maybe if she were younger, we would have gone home with the pink polka dotted shirt paired with the striped green and red shorts, but is that such a steep price to pay when you get to have a great day with your daughter?