On rainy days you need pick-me-ups more than ever. These Fashion Sheer Lace-up Rain Boots add fun, color, and, above all, fashion to your stormy weather ensembles. You’ll be praying for rain on even the sunniest days! Available at oasap.com for only $62
Rich midnight blue hues and a modern art vibe set this Nancybird Dana Bag apart from your average carryall. Soft dove grey leather pieces provide a perfect accent, and the illustrated inset has a lovely watercolor feel. Available at nancybird.com for only $395
We don’t actually need all of our toes, do we? We only ask because we’re pretty sure we’re going to slap these Jeffrey Campbell Woven Lovin Ankle Strap Flats onto our feet the minute they arrive, whether our yards are still covered in eight inches of snow or not. These fabulously patterned flats are simply far too gorgeous to languish in our closets ’til spring. Available at shopacrimony.com for only $107
After a week of precise and deliberate outfit planning, come Saturday, you couldn’t care less what you throw together. As long as the pants don’t have buttons and a blazer isn’t required, you’re happy as a clam. These Sanuk Flurry Sidewalk Surfers are cozy and cute in an unexpected, quirky way. Much like the mailroom boy who may or may not still be snoozing in your bed after a raucous evening of unexpected, quirky romping. Available at sanuk.com for only $120
A carryall is indispensable this time of year when you’re layered up with mittens, scarves, and hats and every store you walk into has the heater cranked up. The Chelsea Bag has a polished aesthetic that’s far superior to that of the canvas tote you usually haul around. Available in red, black or navy, this purse has a timelessness that’ll take you through every season looking chic, not burdened. Available at bodenusa.com for only $218
Kate Spade has been indulging in a little Twin Peaks marathon recently, we think. The best inspiration we can think of for the creation of this Knock on Wood Woodpecker Clutch is Lynch’s infamous Log Lady. Our ideal coordinating accessory? Kyle MacLachlan, please. Available at katespade.com for only $328
When you tailgate, you need somewhere to sit. And once you sit, you’ll need something to drink. And if you drink, you’ll need a place to keep the next drink nice and cold. The Tailgate Backpack Cooler Chair : your football season wingman. Available at favorwarehouse.com for only $48
Some people may see these Elliott Booties as bland, or possibly even unremarkable. What you should be thinking about is how many amazing outfits you could pair these with. Nothing says creative like wearing the same pair of shoes one thousand different ways. Available at piperlime.gap.com for only $175
Better start running now. Otherwise, your summer beer weight is going to layer on top of your winter Festivus weight. And then you’ll have twice the work to put into yourself next bikini season. Get a head start with these adidas Running adiZero Adios 2 W Shoes, a bottle of water, a handful of almonds, and a little motivation. Who knows, maybe cardio will be fun!*
*Probably not, but you should still do it. Available at zappos.com for only $115
We love the industrial aesthetic of the Felt Sling Bag by Carga. Instead of sewing bags and purses, they construct them, fastening them together with durable hardware and industrial materials. The result is a stunner of a bag that’s naturally resistant to rain (just don’t submerge it in water!), and strong enough for daily use. Available at cargabags.com for only $195