An all season outfit is the best kind. It could be summer, spring–ok not winter in Chicago, but winter i a warmer climate–and also, fall. It’s made of basics that you can wear almost anytime of year and just works in most climates (again, except a frozen tundra). That’s why I love jeans with stripes and a pop of red…it always works, no matter what pieces you’re wearing. Also, I bought all of these outfit elements during different seasons (shoes/bag = winter, jeans = spring, tee = summer, blazer = fall). I have a helpful tip when shopping for items that you *want* to wear often; do you want to get the most mileage out of pieces you buy? Then imagine wearing that item three different ways with clothing you already own. It forces you to get creative before you make the commitment and just goes to show that the possibilities are endless when it comes to your own closet. But also note that not items should pass this test–some items are meant to be worn just one way (like a dress, for example).