While re-purposing Summer maxis by way of layering in the Fall is smart, you'll be surprised how often you reach for that sophisticated, one-and-done, impeccably tailored dress that lasts you years. For me, that's this Jonathan Simkhai corset dress ($845), which features detachable sleeves for warmer weather and a pinstripe, asymmetrical hem that helped draw attention to my trusty Nine West mules ($94, originally $144). Splurging on a winning number like this one doesn't hurt when it's versatile enough to wear for so many occasions. (You could even attend a casual wedding in this look!)