Unless otherwise specified, all sizes in this post are listed in women's.

1. A pair of high-rise flare jeans in a floor-skimming length to up the ante on your denim collection. Drama with vintage flair, these will hug and support you in the hips and derriere department with a touch of stretch for that just-broken-in feel.

Promising review: "These jeans are incredibly comfortable. Soft but structured. True to size. High quality." —From Oregon

Price: $94.50+ (originally $158; available in sizes 23–37, including petite and tall fits, and six colors)

2. A classic T-shirt that you'll be so pleased with yourself for snagging at an accessible price. It'll go with anything you pair it with, so you might as well get a couple because, unfortunately, you're a stain magnet, and you know that drive-thru Starbucks doesn't take any prisoners.

Promising review: "I love these T-shirts. I have so many colors and needed a crisp new white one. They are soft and of very good quality." —Vicki28

Price: $22.50+ (originally $34.50; available in sizes XXS–3X and 12 colors)

3. A ruched drop-waist dress designed in a familiar jersey fabrication that you'll find yourself reaching to wear for any fancy or semi-fancy occasion. So soft, this'll feel like a comforting hug around your upper half, while the bottom will flare and flow out. As for its looks? Well, 5 stars.

Price: $99.50 (originally $168; available in sizes XXS–3X)

4. A button-up vest with a satin sheen, aka the staple you'll have a vested interest in all seasons henceforth. Simple yet trendy with a textured finish, it's the sophisticated style that'll instantly elevate your entire outfit — even distressed denim will get a makeover when paired with this.

Promising review: "Classic, from fun to formal. Fitted and chic. Can be worn to work or out. Very comfy." —jesw

Price: $79.50+ (originally $128; available in sizes 00–24 and five colors)

5. And a crewneck vest in a cropped patch-pocket design in case you'd like to have ~options~. This has structure in its seam details and edge in its shorter hemline. Crafted with lightweight crepe, it'll make a fab layering piece.

Price: $99.50 (originally $158; available in sizes 00–24 and in black)

6. A patch-pocket denim mini skirt here to bring some playful, retro energy into your rotation. It's cute, stylish, and the epitome of a season-less look: bare legs, flats, and tucked-in shirts for summer; tights, tall boots, and long-line coats for winter.

Promising review: "Classic J. Crew style. I love this skirt. It’s the perfect style and length for my taste." —Betsy47

Price: $118 (available in sizes 00–24, including tall fits)

7. A leather shoulder bag in fiery and studded shades to really set your fits alight. Even if you opt for a simple getup, it can do all the talking *and* carry your essentials.

Promising review: "I fell in love with this purse as soon as it came into the store. I love the studs on the purse. Perfect size to hold my phone, keys, small wallet, and lipstick!" —NOVA girl

Price: $124.50+ (originally $178+; available in six colors/patterns)

8. A sleeveless chiffon shirt that'll play the role of the "nice top" in your workday dressing saga. Whenever you need a reliable layer to wear under a blazer for meetings, this will be exactly what you reach for.

Promising review: "Great for layering. I love this top as a layering item for work or casual wear. It met my needs, and I’m glad I ordered it." —NOVA girl

Price: $114.99+ (originally $128; available in sizes XXS–3X and four colors/patterns)

9. A merino wool midi for anyone searching for a cold-weather skirt. With its sleek, yet stretchy, construction, this will ensure your lower half looks stylish for the office; however, in reality, all you'll be thinking about is how it replicates the softness of your favorite couch throw blanket.

Price: $198 (available in sizes XXS–3X and in black)

10. A cropped collared jacket built with an abundance of fall appeal. I predict this hunk of a layer will make many an appearance in your foliage-chasing-, brewery-frequenting-themed dump.

Promising review: "Cool and functional. I love the look of this jacket — polished cotton, that old-school Barbour style with a zipper and snaps, corduroy collar, but stylishly cropped with a deep pleat creating a full swing in the back. Super dark olive color is a perfect neutral to go with navy and black — everything, actually! And it's got a quilted lining for functionality. In the XS, plenty of room for sweaters but still looks good with just a T-shirt underneath." —lisak61

Price: $228 (available in sizes XXS–3X and four colors)

11. And a plaid long-line jacket in their signature Barn Jacket™ cut. Because you'll also want an oversize, caboose-covering option for cooler weather — and this one has British heritage-chic written all over it.

Promising review: "The perfect jacket. It can be worn with everything. The price point I felt was high. But it’s an investment piece. It won’t leave the closet for decades." —Gottobefree

Price: $298 (available in sizes XXS–3X)

12. A jersey turtleneck with a slouchy (read: non-constrictive) neck so you won't feel suffocated as you're trying to safeguard yourself from the chill. Better yet, this is designed in a familiar T-shirt fabric, making it the easiest transition for anyone mourning the loss of lighter layers.

Price: $26.50+ (originally $55; available in sizes XXS–3X and seven colors/patterns)

13. A faux-leather A-line skirt in a few rich fall hues that are worth investing in. With infinite styling possibilities, suitable for many settings, this is destined to hog all your attention henceforth because it's just that soft, luxe, and looks helluva lot like the real deal.

Price: $248 (available in sizes 00–24 and three colors)

14. A classic crewneck sweater for a simple outer layer that'll get plenty of your attention for its soft, luscious cashmere construction and versatile nature. Easy to pair with literally any bottoms or skirts, it makes dressing for the chill look timeless.

Promising review: "Best basics. Amazing to layer with tanks, tees, and mock necks. True to size, but can size down for a more fitted look." —FrancesK

Price: $168+ (available in sizes XXS–3X and nine colors/patterns)

15. A cropped cotton button-up that you can rely on when you've got no idea what to wear. Place this above any pair of high-waisted bottoms or skirts; it'll dial up your whole vibe and can play the role of dressy or casual, depending on your mood.

Promising review: "I have six cropped button-up shirts and wear them all the time. To me, the fact that the long-sleeve shirt is oversize makes it ideal to wear outdoors (it blocks the sun and allows air circulation) or indoors (with AC on). The cropped length also fits me very well (I am 5'). I find these shirts functional, casual, and sophisticated." —WT6177

Price: $69.50+ (originally $98+; available in sizes XXS–3X and seven colors/patterns)

16. A suede tote roomy enough to carry everything you need while commuting or for an overnight stay. In an ultra-luxe look, you'll be rich with compliments anywhere you take this.

Price: $298

17. A wide scoop-neck tank that passes the day-to-night dressing test. Easy to wear for work and play, it features tailored seams for subtle structure and a nipped-in waist that'll look high-end over jeans, skirts, or front-pleat trousers.

Price: $69.50 (originally $118; available in sizes 00–24 and in white)

18. A cotton poplin shirt dress that's serving a whole old-money, country-club mood. Its classic, crisp collar paired with a flirty pleated hemline is the perfect combination to upgrade your dress collection, while its drop-waist fit proves this style is here to stay.

Promising review: "I bought this dress in black for a polished yet casual work outfit. Worked perfectly." —jstarr77

Price: $94.50+ (originally $158+; available in sizes XXS–3X, including tall fits, and three colors/patterns)

19. A pair of high-waisted sweater pants worth falling head over heels for. The smooth finish and flared hem read office-appropriate, while the elasticized, pull-on waist and bouncy fabric channel a responding-to-emails-in-bed level of comfort.

Price: $158 (available in sizes XXS–3X, including petite and tall fits, and in black)

20. A pair of beaded suede slingback heels to instantly dress up skirts, dresses, and baggy jeans. You won't regret having this pointed silhouette in your repertoire.

Price: $149.50 (originally $298; available in sizes 5–12 and in black)

21. A pointelle long-sleeve that you'll probably end up living in. Easy to layer under leather, sweater vests, and more, it's finished off with a sweet scalloped trim. Essentially, it's like your regular basics but so much better.

Price: $65.50+ (available in sizes XXS–3X and six colors/patterns)

22. A scoop-neck mixed-media dress that's giving both fancy and comfy in one glorious silhouette. Up top, you've got a cozy, finely ribbed tank bodice, while the elegant cotton poplin skirt fans out below with a crisp and breezy, care-free sensibility. Ballet flats, slicked bun, cardigan, boom — out the door you go, superstar.

Price: $74.50 (originally $148; available in sizes XXS–3X, including petite and tall fits, and in black)

23. A classic linen button-up since it'll soon be your go-to breathable shirt for life. With each wear, it'll soften up and feel more and more like yours, whether fastened up over jeans, open over leggings, or tied up over wide-leg drawstring pants — it's a master class in versatility.

Promising review: "Excellent, relaxed fit. Love this shirt! The material is so airy and soft. The fit is perfect; relaxed but not too baggy. You can dress it up or down." —Lover of Linens

Price: $98 (available in sizes 00–24, including petite and tall fits, and five colors)

24. A pair of mid-rise slouchy jeans for a denim piece you can comfortably move in all day, and, quite frankly, will end up living in daily. They go with every top you have in your closet; wear them for days or nights — just imagine coffee dates in booties and wine weekends with kitten heels peeking through? Sublime.

Price: $158+ (available in sizes 23–37, including petite and tall fits, and three colors)

25. A pair of leather ankle booties with a buttery-soft, sock-like stretch and a foot-forming feel for spicy — and comfy — fall footwear delivered. There's not much these won't go with, so if you're on the hunt for the perfect LBB (little black boot), these are it.

Price: $209.50 (originally $298; available in sizes 5–12 and in beige)

26. And, finally, a pair of high-waisted straight-leg trousers for a style you'll be glad you have hanging in your closet. The pleated seam provides a luxurious, elegant touch that can be softened when paired with knits in the fall and satin layers in the spring and summer.

Promising review: "Perfect for work! The material is soft, and the fit is elegant. Love it! I have three in different colors." —laura from the caribbean

Price: $158 (available in sizes 00–24, including petite and tall fits, and six colors)

Reviews have been edited for length and clarity.

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