Ahhhh, transitional weather is upon Us. I've lived through the summer-to-fall shift for 28 years, but I still haven't mastered transitional dressing. This year, it's my goal to finally curate the best wardrobe for those in-between weather days. To do so, bomber jackets are at the top of my shopping list. These lightweight jackets were initially designed for the military, but over the years, they've made their way into mainstream fashion. Bomber jackets feature a loose, boxy silhouette and are often made from leather.