Coming from J.Crew and Jenna Lyons' tutelage, Somsack Sikhounmuong is poised to make Madewell more woman-friendly, with made-to-last work-to-play staples that'll more than justify their sticker price. The designer, taking away some of the super-trendy pieces women older than 16 might struggle to wear, plans to streamline, clean up, and elevate Madewell's products, which will debut in the forthcoming spring '14 lookbook. So, while we wait for that to be unveiled, we reached out to Sikhounmuong to pick his brain. Ahead, five of our common styling woes and the five Madewell-approved solutions that provide a fix. Because we all need a little help sometimes.