Since a good part of my week is spent in more professional clothing for my office job, I am happy have comfortable pieces that still look polished for when the weekend rolls around. I am not a sweatpants kind of gal, but a comfortable pair of jeans, flat boots and an easy-to-wear coat can feel very similar. I picked up these Sloosh rain boots last year because my Hunters were beginning to look haggard (now they have been reduced to my really bad weather boots), and when they arrived I was shocked at how perfect they were for daily wear. I don't always find rain boots to be suitable for sunny days, but these Sloosh boots (love this style as well!) are seriously the coolest and most versatile all-weather boots I have ever come across. They can be extremely fitted around the ankle so it can take a bit of patience to get them off (or a second hand occasionally - LOL), but they are super comfortable to wear during the day and look like great sans bad weather! And of course I had to transition my hats from straw fedoras to wool ones for winter. It's still quite sunny and bright during the winter so I am a big fan of using hats as sun protection as much as my SPF. I picked this one up in two colors from J.Crew and love the way it fits. I still haven't mastered the art of how not to get my makeup on the inside brim of the hat so that is my only drawback when wearing them. But when that wind picks up and the temperature drops, I am just happy to have something to help me stay warm and block out the wind from my face.
Coat - Club Monaco (old but similar here) | Jeans - Hudson | Boots - Sloosh Boots | Gloves - J.Crew (similar here) | Hat - J.Crew | Bag - Louis Vuitton