Unless otherwise specified, all sizes in this post are listed in women's.
1. An oversized corduroy shirt if your favorite word in the English language is "shacket." Pop this on over any old outfit for a bit of warmth and casual charm.
2. A pullover puff-sleeve sweater for days when there's a bit of chill in the air but you really want to opt for a sunny silhouette. I present to you the perfect solution.
3. A pair of Ugg slippers so you can pad around your house in the early morning holding your favorite mug without the burden of chilly feet.
4. A pair of loose-fitting, wide leg palazzo pants for the days when you need to wear pants but just can't bear to break out the trousers.
5. A gorgeous floral print maxi dress if you can't stand the feeling of being constrained by your clothes. This beauty has a smocked waist and nice flowy skirt for maximum freedom.
6. A cropped pullover you can wear as part of an athleisure look or a normal daytime vibe. It all comes down to styling.
7. A V-neck button-down dress that strikes the perfect balance of comfortable and adorable. Here's lookin' at you, row of buttons!
8. A pair of high-waisted leggings for hiking, lounging, and literally anything in between. What would we do without these stretchy little wonders?
9. A tie-waist cotton sheath dress to upgrade your office style without succumbing to traditionally constrictive work clothes. It's been a while since you got a new "I'm a boss" outfit. Treat yourself.
10. A casual midi dress you'll be so happy to have on-hand on days when you need to look cute ASAP. Sleep an extra 15 minutes and let this dress answer the question, "What should I wear today?"
11. A dreamy floral wrap dress ready to accompany you for any and all frolicking you plan on doing this summer.
Promising review: "This dress is perfect. Perfect fit. Comfortable. Light and breezy. Good quality. I have worn this dress many times and always get compliments on it. I highly recommend this dress!" —jillpoletti
Price: $47.99 (available in sizes S–XXL and 40 colors/prints)
12. A minidress for days when you just need a little extra boost. Adorable puff sleeves are good for that, and I bet we could get research to back that up.
13. A classic swing dress whose slightly ruffled sleeves will differentiate it from the rest of your collection. Listen, you don't need to defend your love of an A-line style to me!
14. A soft T-shirt dress so you can look casual and cute at a moment's notice. And with summer almost here, it's time to get some nice cool options for when the sun's doing its thing.
15. A ruched bodycon dress that'll shepherd you through a killer night on the town. Don't worry, it's nice and stretchy so your signature moves on the dance floor won't be constrained.
16. A fuzzy hooded cardigan for anyone who's ever looked at a Teddy bear and thought, "They look super comfortable."
17. A super cute collared dress if you want to play a hand in bringing back early '00s indie sleaze. As a lover of a collar myself, I salute you.
18. A pair of bike shorts, aka one of the most essential wardrobe pieces of all. When summer is in full swing and the sun is doing its thing, there's nothing these shorts, an oversizes tee, and some chunky sneakers can't accomplish.
19. A stretchy jumpsuit to swaddle you in stretchy goodness while also making you look put together as hell. Whether you go for sneaks or wedges, you've got a look.
20. A pair of cutout floral flats reviewers promise are nice and comfy. And I mean, come on. They're almost too cute to handle.
21. A pair of high-waisted dress pants you can easily wear to work and, much more importantly, can rock at happy hour with your friends afterwards.
Promising review: "These might literally be the most comfortable pair of pants that I own that I can wear at the office. They make my butt look great while still giving the flowiness that I was looking for. The only downside is that they're a little thin so they aren't very warm but they'll be great in the summer!" —Tabi
Price: $28.99+ (available in S–5X and 30 colors/styles)
22. High-waisted rolled denim shorts because the only thing that improve the classic denim experience is a subtle elastic waistband to ensure you can, ya know, breathe and stay comfortable in these all day long.
Promising review: "These are the best summer shorts. I wish I had these in several colors. The fit is spot-on. I purchased the blue denim and the black and both are great colors, but I want more colors. I also love the elastic waistline." —doub515
Price: $24.99 (available in sizes XS–XL and five colors)
23. A pair of Toms block heels for anyone looking for as comfortable a heel as possible. A nice cushy footbed does the trick for keeping you upright at weddings, work, and out dancing.
24. A goes-with-everything waffle-knit top you'll find yourself throwing on several days a week this summer, I basically guarantee it. This baby comes in 18 colors, so it may be worth it to get a few upfront.
25. A pair of trendy cushioned slides to keep by the door for last-minute errands, neighborhood walks, and walks with Fido.
26. A tie-waist mini sweater dress so you can stay wrapped in comfort at events, dinners, and the like on crisp summer evenings. Dining on the patio, anyone?
27. And a short-sleeve maxi dress you'll be relieved to know is in the closet on days when you're just not sure what to wear. Behold: your beloved go-to.
The reviews for this post have been edited for length and clarity.