There are a handful of Janie & Jack styles I order year after year in the next size up, knowing they’ll be worn and well loved before being passed down to the next brother in line. This round-up includes some of my tried-and-true favorites, like the classic navy quilted jacket (perfect for everything from the school playground to weekend apple picking!) and these adorable suede Chelsea boots I’ve been buying since our almost six-year-old first learned to walk. I love that their pieces are durable enough for everyday wear but also sharp enough for school picture day or family photos. Investing in a few high-quality essentials like these makes getting all four of our boys dressed for fall feel a little easier (and a whole lot cuter!).