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This is my four year old, Henry, wearing the dumbest shirt ever. It’s a soccer jersey from our local rec department from at least three years ago—and the best is it wasn’t even his team. It was from one of our older kids’ teams, which makes it a tri-colored, hand-me-down team jersey that was free to start with. I would have scoffed at this several years ago; it would have appalled me that we would even own a piece of clothing that looks and smells like this polyester gem. But somehow not only one but now two kids have worn it to school, and I’ve washed and put it away a thousand times.

Even though they wear the worst stuff sometimes, though, I still dream about them being fashionable. Here are some of the items for my two older boys that I’m swooning over this season:

Oh my gosh so cute. I think this sweater would look adorable on Henry, who is turning five this winter. I love the primary colors, and he would love the hood! On a recent trip to Boston, we visited the BEST children’s boutique called Cou Cou. It had all the very best elements of a great boutique; it reminded me of The Shop Around the Corner in You’ve Got Mail (sigh—my favorite movie ever). The shop’s owner, Astrid, is so gorgeous and personable, and I wanted to buy every single thing in there. But this sweater by Nanos was at the top of my list. I think Henry would look like an actual movie star in it, and it’s giving me all the heart eyes!! To visit her store online and see this sweater plus all the other great clothes and gifts she sells, go to www.coucou-boston.com.

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This sweater, from Buho, is what I wish Jack were wearing now. He is turning eight this winter and is soooooo handsome. His clothes are usually almost as dumb as Henry’s, but oh my word he would look amazing in this sweater! I can never over a classic tweed sweater, and the elbow patches make this one perfect. Love it. You can find this on www.coucou-boston.com, as well.

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This outfit actually does look a bit like the boys when they go to church on Sunday these days, but I’m loving the leather belt. We need to add one to the boys’ wardrobes ASAP, because I think this belt elevates this outfit from kinda normal to heartthrob status. And this shirt reminds me that at the top of my list for wardrobe staples that I wish I was adding to the boys’ closet this year are flannel shirts. I found this really perfect one on www.shopfoxandkit.com that’s made by Tea Collection, which has always been one of my favorite brands for both our boys and our girls. As far as winter shirts go, I don’t think you can go wrong with this classic!

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I feel like these looks would be a pretty good start to the boys’ fall looks, if I lived in that alternate universe where they didn’t want to only wear ugly soccer jerseys and athletic shorts all the time. Clearly, I’m a huge fan of all things red! This is just the first of many posts I plan to do about what I wish our kids were wearing, because I’m past the stage of parenting where I can control what everyone dresses like. But thanks for letting me daydream with you!