Unless otherwise specified, all sizes in this post are listed in women's.
1. A slip skirt to remind you of that *one* time you had the idea to skip through a field of daisies but then soon found out bugs live in fields....so this floral skirt will just have to fill that urge instead.
Promising review: "I love this skirt! It looks great paired with a graphic tee or just a simple tank top. It can be dressed up with heels, dressed down with flip-flops or, to give it an edge, it looks great with Doc Martens. I love its versatility as it can be worn in the summer, or going into fall paired with a jean jacket. This skirt is a must-have staple to add to one's closet." —Veerider
Get it from Madewell for $98 (available in sizes 00–16).
2. A polka-dotted beauty that'll act as the punctuation in your style statement 😉.
Get it from Petal & Pup for $59.95 (available in sizes 2–10).
3. A plaid mini dress for anyone who actually loves Back to School season AKA treating themselves to a slew of new outfits.
Get it from American Eagle for $44.95 (available in sizes 2XS–2XL and two styles).
4. A fabulous midi skirt that's available in an unreal amount of colors so when you inevitably fall in love with it you can buy it five more times.
5. A romantic cottagecore number that, while it looks fancy and mesmerizing, is actually super lightweight and comfortable for a variety of seasons.
Simple Chics Boutique is a Columbia, South Carolina-based shop featuring gorgeous clothing, accessories, and home accents.
Get it from Simple Chics Boutique on Etsy for $39.60 (originally $44; available in sizes S–XL and five colors).
6. A darling smock dress you won't be able to help but take a ton of photos in — good luck trying to pick *just one* to go on your Instagram feed.
Get it from Boohoo for $14.40 (originally $36; available in sizes 12–20).
7. A circle skirt with attached suspenders that'll add a little *somethin', somethin'* to your typical (and predictable) skirt-and-a-basic-tee uniform.
8. An off-the-shoulder dress you can use to show off your sun-kissed shoulders and a lil' leg. If you've got it, flaunt it!
Beginning Boutique is a woman-founded business based in Brisbane, Australia.
Promising review: "The cutest little puffy dress with puffy sleeves. So comfy and pretty. Received compliments all night. I love it. Thank you so much." —Alexndra M.
Get it from Beginning Boutique for $49.99 (originally $69.99; available in sizes 2–10).
9. A denim mini dress that'll look amazing alongside the many chunky boots you bought on sale at the end of winter last year — you can totally pair it with stockings when it gets chilly again!
Promising review: "This is a darling dress! Its length is perfect for me at 5' and the sleeves are above my wrists. An excellent dress for New England spring! The material is thick denim. I will wear it with leggings now and sandals later. Highly recommend!" —mintandparsley
Get it from Free People for $128 (available in sizes XS–L and five colors).
10. A midi wrap dress that'll look incredible with the dazzling necklace and earrings you already own — who knew finding an outfit for that wedding you have coming would be this easy???
Get it from Boohoo for $30 (originally $60; available in sizes 12–24 and four colors).
11. A floral sundress you can count on to brighten your wardrobe and your mood all the while keeping you cool (three cheers for lightweight jersey material!).
Get it from Boohoo for $10.80 (originally $24; available in sizes 14–20 and three colors).
12. A vest dress that'll convince anyone who glances your way that you are, in fact, cooler than cool. Add sunnies and an oversized hat to complete the *chill* vibe.
13. A breathtaking dress you can easily wear to a bridal shower, a date, brunch with your friends, dinner, wherever! It's absolutely stunning.
Christy Dawn is a small business that makes sustainable fashion with deadstock — their clothing is absolutely gorgeous and, IMO, worth every penny just from the looks of it! They site even offers a breakdown as to why each dress costs what it does, so you'll really know where your money is going.
Get it from Christy Dawn for $398 (originally $498; available in sizes XS–XL and six styles).
14. An off-the-shoulder ruffle dress that very well could have inspired the creation of the enchanted pink rose from Beauty and the Beast. It's gorgeous — and you will be, too, while wearing it!
Get it from Boohoo for $30 (originally $60; available in sizes 12–24).
15. A floral midi dress that'll help you achieve a look that says Bridgerton but on Casual Friday. It's stunning and would be a lovely addition to your wardrobe.
Promising review: "This dress is STUNNING. It's the kind of effortless glamour I've needed in my life and I can't wait to wear it everywhere all summer. The material is soft, the sleeves are adorable, the floral pattern is lovely and it's just all around wonderful." —Madjacks16
Get it from Madewell for $128 (available in sizes 2XS–2X)
16. A curve-hugging high-neck dress for when you want to channel your inner Kardashian and embrace an autumn color palette.
Kloset Envy is a Black woman-owned small business based out of Los Angeles, California that sells fabulous fashions.
Get it from Kloset Envy for $58 (available in sizes XS–L).
17. A high-waisted pleated skirt you'll want to twirl around in like Beyoncé on her haters...to generate a breeze because, let's face it, it's hotter than hell.
Promising review: "Bought this for a trip to Italy and was AMAZED at the high quality. I’m a curvy girl and would normally get an XL, but after reading reviews about [the] stretchy waistband, [I] opted for the L, and it was a perfect fit. It hangs beautifully and is very flattering. Highly recommend." —Dr. Shannelle
Get it from Amazon for $22.99+ (available in sizes S–2XL and 35 colors).
18. A sweater dress that'll leave you looking *bad to the bone* whether you plan to wear it for a casual Halloween hang or to channel spooky season whenever the mood hits.
Get it from ModCloth for $89 (available in sizes XS–XL and 1X–3X).
19. A black denim skirt you can pair with your favorite band tee for an edgy look one day then mix with darling stockings and a cardi the next. We loooove a versatile piece!
I have a very similar skirt from Madewell and have gotten so much use out of it over the years! It's forgiving in the waist, matches so many things I already own, and is a basic I never knew I needed.
Get it from Madewell for $69.50 (available in sizes 23–30)
20. A midi skirt that'll help you flawlessly transform into a modern day Disney Princess without breaking the bank. Honestly you *do* deserve much more than this provincial life and this skirt knows it.
Promising review: "I absolutely adore this skirt. This is the fifth one I’ve ordered. I regularly get compliments on it and occasionally make others jealous when I twirl and I show them it has POCKETS too! It’s work-appropriate, as it hangs to my knees, and can also be worn in social settings. The material is sturdy, the color is vibrant and doesn’t fade, and it’s never bled onto any of my clothes." —Amazon Customer
Get it from Amazon for $19.99+ (available in sizes XS–2XL and nine colors).
Check out our deep dive on this skirt for more styling ideas.
21. A standard high-waisted denim skirt, because the one you've been wearing for the last decade has likely seen better days.
You simply can't go wrong with Levi's denim!
Get it from Revolve for $80 (available in sizes 24–27).
22. A baby doll dress with a darling plaid print that'll make you want to plan the cutest picnic day anyone ever did see complete with a charcuterie board, wine, and this perfect outfit.
Tuesday of California is a small business that incorporates deadstock and sustainable fabric into their clothing — amazing.
Promising review: "I want to wear this dress every day! It’s very light and gauzy but still drapes beautifully and maintains its shape. I have a larger bust and don’t feel restricted at all up top." —Maia
Get it from Tuesday of California for $160 (available in sizes 2XS–XL, 1X–2X, 7X, and five colors).
23. A pleated and tiered off-the-shoulder dress you can twirl your heart out to while giving your all to the middle of the dance floor at a wedding. I'd say all eyes will be on you but we wouldn't *dare* want to steal a moment of the happy couple's day 😉.
Promising review: "OMG! Awesome!!!!! It drapes beautifully. I plan to wear it on my shoulders, and the elastic seems strong enough to hold. I bought the white and it’s light and airy — not see though at all. I'm so thrilled. I will buy it in black ASAP!" —LB
Get it from Amazon for $34.99+ (available in sizes S–XL and 18 colors).
24. A loose-fitting maxi dress so versatile, you'll easily be able to rock it at brunch or at the beach.
Promising review: "Love this dress. I have a few different colors. They can be worn casually, or dressed up with accessories. The material is soft and silky. Washes nice, I wash mine in the machine on cold and hang to dry, they still look new after several washes. This dress is definitely made for taller women, I'm 5'8" and I tie the front in a knot, the back still slightly touches the ground...but I like it that way." —Michelle Castillo
Get it from Amazon for $18.99+ (available in sizes S–2XL and 42 styles).
25. A quirky skirt you'd likely describe as *~out of this world~. I'm quite certain Miss Frizzle would approve of this look, heck, even Jeff Bezos and Elon Musk might at this point!
Get it from ModCloth for $69 (available in sizes XS–XL and 1X–4X).
26. A black halter dress you better believe will leave your date's jaw hanging out on the floor when they see you enter the room — it's absolutely FIRE.
Kin by Kristine is a Black woman-owned small business based in Los Angeles that sells fabulous fashions.
Get it from Kin by Kristine for $80.95 (available in sizes 14–26).
27. A denim cow print mini skirt that'll tell all the pants you don't enjoy wearing to moooooove over because it's gonna be your new go-to option.
Get it from Urban Outfitters for $59 (available in sizes XS–XL).
28. A laid back shift dress featuring a dainty floral design you'll pat yourself on the back for buying when you get invited to a last-minute BBQ and need something cute 'n' casual to wear.
Get it from Asos for $35 (available in sizes XS–XL).
29. A midi dress with pretty buttons all the way down the front you can count on to look gorgeous alongside the Pumpkin Spice Latte you're likely to pose with next month. It's NEVER too soon, IMO.
Promising review: "I was a little nervous this dress would be too large and flowy, but it's excellent. It doesn't fit me like a potato sack at all! It's tighter around the bust for some tasteful cleavage and then flows out from there and hits me mid-calf. I want to wear this dress every day this summer. It's light, easy to dress up or down, and super comfortable." —Benj
Get it from Madewell for $108 (available in sizes 2XS–XL).
30. A comfortable striped maxi dress complete with pockets that'll make it a front runner for your favorite item of clothing.
Eclectic Bella is a Black woman-owned small business based out of Los Angeles, California that sells gorgeous clothing.
Get it from Eclectic Bella for $36 (available in sizes S–L).
31. A whimsical dress from Her Universe that'll have you jumping up and down for joy like Totoro discovering umbrellas.
Get it from Hot Topic for $31.92 (originally $39.90; available in sizes XS–XL and 2X–3X).
32. A vibrant maxi skirt you'll put on, take on look at yourself in the mirror, and say "well, orange I glad I bought this!"
33. A darling mini dress covered in florals you won't be able to help but twirl around in and take a ton of boomerang videos for Instagram.
Promising review: "Tried this dress on in store and I love it! My husband loves it too! Wore it all day and I was turning heads and getting compliments all day! Going to the beach next week and taking this with me! I love that it’s made of cotton and has sleeves because, let’s be honest, AC indoors is often too cool during the summer and sleeves are appreciated. I love that I can wear this to church, a baby shower, a wedding, summer picnic, to the beach. It’s versatile for it all!" —Brownie
Get it from Madewell for $128 (available in sizes 2XS–2XL).
34. A lightweight maxi skirt starring an adorable ruffle waistband (s'cute) you won't be able to stop yourself from ordering in a variety of colors (take it from someone who actually owns it).
After putting this skirt in tons of posts, I finally caved and ordered one for myself. Reviewers love this skirt and for a reason — it really does live up to the hype! I paired it with a high-neck tank, a denim jacket, and sneakers and felt super cute when wearing it to my best friend's baby shower. I love that there aren't any buttons or drawstrings, you just pull this baby on and feel like royalty. The pleats are adorable, the ruched waist is fun, AND it has pockets!!! I'm literally going to place an order for another one as soon as I can decide between the green and the pink. Screw it, maybe I'll just get both.
Get it from Amazon for $22.85+ (available in sizes S–2XL and eight colors).
35. A full circle skirt that'll let you live out your Pride and Prejudice fantasies — it's elegant and absolutely has the period-piece-main-character vibe you didn't know you always wanted.
Barkwood Clothing is a Black woman-owned small business based out of Los Angeles, California that sells, well, clothing!
Get it from Barkwood Clothing for $295 (available in sizes XS–L, 1X–5X, and two styles).
36. And a luxurious velvet swing dress with green stripes that remind me a bit of the costumes cast members wear at The Haunted Mansion in the Disney Parks, but in a way more fashionable way. Anyone down to Disney Bound?
Promising review: "I love this dress. I needed it as soon as I saw it — I actually purchased for the upcoming holiday season. I’m a medium in everything and this was no exception — I'm 5’6” and it hit a perfect few inches above the knee. What a great price too! Can’t wait to wear this!" —Amanda C.
Get it from ModCloth for $59 (available in sizes XS–XL and 1X–3X).