Let’s talk about something very near and dear to my heart… dresses with pants. Yes, like most things nowadays (looking at you Birkenstocks) it’s a slippery slope towards frump. Done right, however, it’s daring in a subtle way and the perfect transition outfit for those nice days that aren’t quite warm enough to wear a dress on it’s own (or maybe you have an amazing dress that’s just a liiiiitle too short to respectably wear out in public). Here’s my take, at the Distillery District in Toronto. If you follow me, you know by now that I love this dress so I figured it was about time I featured it. Do you love dresses with pants yet? Don’t worry – more inspiration photos for styling to come.