When I find a flattering little black dress, I don’t hesitate. I take it home. It’s something I will wear, most likely multiple times, and it will always look classic and chic. This version is sweet, comfy, perfect for every season and inexpensive. Which brings me to my bag, which is not cheap, but made a little more reasonable with the fact my dress is under $20. This Rebecca Minkoff ‘Love’ Crossbody is the perfect size. I can fit everything I need, but it’s still completely manageable and my go-to as a date-night bag. I don’t know why I waited to buy it (maybe I was waiting for a bargain dress to justify it). The chain is gorgeous and all black means I can pair it with ANYTHING. It’s also available with a gold chain, and several colors for you more adventurous types (or if you already own a perfect black bag).

My over the knee black boots are comfortable, perfect for fall and winter, and are FLAT (I can wear them even when running errands!). They can be dressy or casual – think jeans and a white button-down. My version is from H&M last season, but I’ve linked my top picks for this year. This statement necklace makes the outfit, right? I love pairing it with a plain white tee, too. It isn’t just for dress.

Find all the items for a chic work look, date night, or lunch with friends outfit below.