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Unless otherwise specified, all sizes in this post are listed in women's.
1. A pair of Zella leggings, but not just any regular leggings — a pair that *has pockets* because we love to be comfortable and practical.
2. A pair of the trending Ugg Ultra Minis, with a twist. These will let you enjoy the immense comfort of Uggs and embrace the trend, but still stand out from the crowd in a unique and bold color.
3. A Free People slouchy tunic designed to be warm and perfectly oversized. Great to wear as a top with jeans in the winter, or a dress with boots in the fall.
4. A basic rounded v-neck t-shirt because why pay full price for your staple pieces when you could just get them on sale?
5. And while you're at it, a wire free bra to go perfectly under that t-shirt to create a smooth (and comfortable!) base.
6. A Madewell bandana with so many uses — worn as a kerchief, tied on a bag, wrapped in your hair — you'll never stop coming up with ways to wear it.
7. A pair of Circus by Sam Edelman faux leather boots that are a perfect compliment to any fall outfit. With a stretchy ankle, you won't find yourself struggling to get these on over your heels.
8. A pair of Good American cropped skinny jeans because no, they aren't canceled, no matter what Gen Z says! Plus, these are so stretchy and comfortable you will actually want to wear jeans instead of your leggings.
9. A Free People cardigan with textured ribbing and a relaxed fit for a cute outfit that is also comfortable!
10. A long sleeve crew neck that will become a fall staple in your closet. The cotton blend is breathable so it's a great transitional piece or perfect for layering.
11. A block heel sandal so you can look cute but also feel comfortable *all day* while you wear them. These simple heels are easily dressed up or down, and the braided leather embellishment really pulls it all together.
12. A side ruched body-con dress that takes a simple jersey dress and adds some *pizzazz* to the side. A perfect dress to wear with a light jacket for one of your last outdoor dinners of the season.
13. A merino wool beanie because even if we may not want it to, winter is coming. You need to stay warm, so you may as well be stylish, too.
14. A hooded, quilted jacket that is also water-repellent! With all the different features (thumbholes, straps to carry when you're hot, attached bag to put the coat into on those mornings you think it'll be cold but soon regret your outfit choices by about noon) you're definitely going to find a reason to make this your go-to jacket.
15. Beyond Yoga's midi legging designed to stay in place throughout your entire workout, but nice enough to be worn with a sweater for dinner afterwards.
16. A Kendra Scott pendant necklace because if you watched any of Alabama sorority rush on TikTok then you know these are all the rage. But if you have no idea what I'm talking about, the 14-k gold plated necklace speaks for itself with its beautiful birthstone pendants.
17. A Free People turtleneck sweater for the perfect combination of oversized and put together. The chunky knit detailing is incredibly soft and warm, so you won't have to worry about freezing at the next tailgate.
18. A pajama set so you can look cute, even in your dreams, with a fashionable collared, button-down shirt and matching shorts.
19. A leather clutch with an incredibly simple silhouette, but a shockingly large interior. With six card slots, a snap pouch, and space for your phone, you'll never find yourself reaching for a traditional purse again.
20. A pair of high waisted shorts that are lightweight and stretchy so you can feel good just hanging out, or while working out. Plus, they have *pockets* so what's not to love?!
21. A pair of Brooks running shoes with the perfect combination of cushioning and support. Reviewers rave about the comfort they provide no matter the distance of their run or amount of time on their feet.
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