In college I had a black, A-line skirt that I fondly called “Old Reliable.” For days when an inventive outfit just didn’t come together, I knew I could pull on this comfortable, versatile skirt and not think twice. This collared shift dress from H & M reminds me of Old Reliable – it’s a flattering, timeless piece that can be dressed up or down and accessorized with just about anything. The green lenses and cool shape of these Warby Parker sunglasses (1.) give off a slightly retro feel. Delicate and understated, this ampersand necklace from Etsy (2.) would pair well with the collar on the dress (3.). One of my favorite jewelry trends is the ear jacket; these ones from Rue Gembon (4.) add a little bit more edge than your average pearl post. Winter calls for lots of lip balm, and I just picked up this tinted tube by Maybelline in Berry Soft (5.). For those of us on the go, the classic black tote means utility and effortless style. This leather carry-all from Cuyana (6.) is available with or without the monogram. This Zara coat (7.), when paired with sophisticated staple pieces, is leopard print done so right. A quirky umbrella like this one from J. Crew (8.) will bring a little cheer even on the rainiest of days. Finish off this outfit with the sweetest pair of menswear-inspired oxfords (9.).