Pink Plaid Boy Shirt - by J. Crew

I don't quite fancy how this shirt is presented on the vendor's website, as it really hides it's potential as a great addition to your wardrobe. Anytime you have a piece that swings in the bland direction as readily as it does in the trendy direction, you want to avoid pairing it with something that is equally ambidextrous. First and foremost, you want to make sure a boy shirt like this fits well and is not too frumpy. Second, you want to pair it with a more blatantly trendy piece so that it tends to look more like a mild fashion statement than a total lack of effort. Most importantly, you need the right shoes to offset any potential frumpiness! No white sneakers with this shirt. Try it buttoned up three quarters of the way, a few antique gold chains cascading over, sleeves rolled up, skinny cargos (such as J. Crew's titanium Trouper Pant), and sleek brown booties.