Ankle booties are great and all, but it's getting cold and it's time to bring out the tall boots! I tried wearing my ankle boots and skinny jeans the other day and I froze. My ankles were cold and I needed some thick warm socks instead of thin little no-show socks. I've posted a lot this fall about ankle boots and skinny jeans and the look is still current, but if it's getting cold where you are, know that it's just fine to bring out your tall boots. Skinny jeans still look the best with these too, because there's no bunching at the knee and you'll have a smoother look than a jean with more fabric. Some people have slim calves and have a hard time finding a boot that doesn't slap when they walk. If this is you, try a tall thick boot sock over your skinny jeans and under your boots. My shiny Hunter Tall Gloss Boots have an adjustable strap that works very well for this problem. I spent 3 years trying to decide if I really wanted to spend $150 on rain boots, and I'm so glad I finally went through with the purchase. They actually make me excited to leave the house when it's pouring outside, and that's worth a lot! Seattle hit a record for rain last month and I wore them at least 15 times that month alone, bringing my cost per wear to under $10 per wear. They are the perfect boot for rainy day drop-off and pick-up, stomping through the muddy kale patch at the farm every week, and splashing in the puddles with my 4-year-old. Pictured: Blank Denim Skinny Jeans. Photo by Amy Wimber Photography.