1. These striped silk pants that look fancy without feeling stuffy.
2. A pair of Superga metallic trainers for satisfying your inner sneakerhead.
3. A packable, hooded rain jacket that won't look frumpy when layered -- even in the dreariest of downpours.
4. This sequin bomber jacket because shiny is your favorite color.
5. Some Sam Edelman rain booties (and don't look like rain boots) to give your wellies a rest.
6. And a pair of classic Hunter wellies for stomping around in mud and puddles at music festivals, your farm, and other dirty but fun locales.
7. A four-pack of plain v-neck tees because you can never quite seem to find yours when you need them.
8. A wipe-clean Tumi travel duffel that'll fit snugly under your shoulder, in an overhead airplane compartment, or under a seat.
9. Some shiny hot yoga shorts so you'll look extra fine in all kinds of positions...including sitting on the couch.
10. A fun, fringed Rebecca Minkoff cross body (that comes in sooo many colors) for when you feel a little rock 'n' roll.
11. A Levi's faux-leather jacket you can throw on with most anything.
12. A non-black collapsible umbrella you can stick in your bag -- and spot when sometime tries to steal it as it dries by a door.
13. A breezy Hawaiian shirt for some luau you'll eventually attend one day.
14. Some neutral wedges you can wear to outdoor events, beach weddings, work, whatever, that'll make your legs look, like, a mile long.
15. Some Beyond Yoga leggings that'll stand up to all kinds of sweaty activity and machine washes.
17. An adorable oversize tote in a rainbow of colors that you'll keep by your side for the rest of eternity. Maybe.
18. Some lace-up mom shorts with room to let your outer thighs breathe.
19. These Bass penny loafers for a classic you can lean on time and time and time again.
20. These rugged Frye motorcycle boots already worn in to bad-ass perfection.
21. A colorful J. Crew linen blazer for when you need to look polished, but only a bit serious.
22. This playful striped set you can wear on vacay...or just to sit around in at home. Up to you!
23. A Tone it Up x Bandier sports bra so pretty you'll drag yourself out of bed in the morning to ~show it off~.
24. A faux-leather backpack worth its weight in gold...and could probably carry it, too.
25. A comfy lamé Ivy Park shirt for stepping up any damn outfit.
26. This lace-accented shirtdress that looks perfectly styled flying solo.
27. And a packable Calvin Klein down coat that's worth buying now and storing in the nice handy little bag...because winter is coming.
Reviews have been edited for length and/or clarity.