A great pair of ankle booties is definitely a must-have for fall, and this pair is so comfortable! I bought them last year and wore them literally every day for months, which is crazy because I have never before found a heeled shoe that I wanted to wear more than one day in a row. I'm seriously considering another color.
When it gets a little too cold for ankle boots or I just want to switch things up, these riding boots have been my favorite for years - I think my original pair pre-dates this blog! After an unfortunate zipper incident where I literally ripped the zipper off of the boot while traveling and then abandoned them out of anger in our hotel room, I repurchased the same pair because I missed them so much. Before my amazing ankle boots I wore them basically every day for about 9 months straight through rain and snow and ice for four years in a row, so I think I can forgive them a faulty zipper.
When it's time to pull out boots, it also means it's skinny jean season! I love skinny jeans year-round, but they're definitely essential when you need a pair of pants that you can tuck into taller boots. This pair from Madewell is my current favorite, they have the perfect amount of stretch without stretching out, and the lack of distressing means I can wear them during Chicago's cooler weather without getting frostbite.
A plaid shirt is a definite must for fall, and I love this flannel version I picked up from J. Crew Factory last season. It's cozy, it's warm, and can be easily dressed up or down. Want to switch things up? Their classic gingham shirt is a perfect choice, and is thin enough to layer.
While the weather stays warm, I like to switch off between my utility vest and jacket. Both are so easy to wear and basically go with everything, and help you figure out what to wear during those days when it's sixty degrees when you leave your house in the morning but eighty by the time you're heading to lunch.
For cooler and rainy fall days, a lined and hooded jacket is the best. I picked up mine at Nordstrom Rack last spring and somehow managed to wear it a ton before summer weather hit. Something with a hood is not only great for chilly weather, but is also necessary in Chicago where it's usually so windy that an umbrella doesn't always work on a rainy day.
Want to see me wearing almost all of these at once? Yup, turns out that happened ;)
What are your go-to pieces for fall?
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