1. A square-neck, sleeveless maxi dress that will quickly become your new favorite item of clothing. It's giving expensive garden party vibes, and I am here for it.

Madewell

Promising review: "This is an amazing wedding guest dress. It's easy to dress up or down. Not to mention, it's incredibly comfortable, accentuating your curves without clinging to them. The pleats at the bottom make it feel extra special! It hits at the ankle if you're 5'3"-5'5". If you tend to have a smaller torso/waist/chest, you may want to size down."  —Summer

Price: $188 (available in sizes 00–16)

2. A smocked boat-neck top to add a ton of ~texture~ and depth to your sunny day wardrobe. If you're not a fan of ironing (which is basically everyone), this top's for you.

Madewell

Promising review: "These are perfect. Most smocked tops are so stiff, they don’t want to lie right. This one is soft enough that it moves with you. Perfect with barrel pants or jeans or shorts. Not too snug either!" —Clotheshorse

Price: $58 (available in sizes XXS–XXL and in six colors)

3. A pair of high-waisted denim shorts because jean shorts are a summer classic for a reason (versatility, breathability, timelessness), and these ones are the perfect base for many looks.

Madewell

Price: $74 (available in sizes 23–33, 14W–20W, and in two colors)

4. A relaxed linen shell top that's giving luxe "I vacation at my mansion in Nantucket" vibes, even if you've never stepped foot on Nantucket in your life. I won't tell if you don't.

Madewell

Promising review: "It is extremely cute, though you wouldn't expect that looking at it. I have it in two colors, black and oat, and get compliments on it whenever I wear it. It's also really lightweight, so it will come in handy in the upcoming hotter months. It fits kind of boxy, but I like that." —AllisonB

Price: $78 (available in sizes XXS–XXL and in three colors)

5. And a linen maxi slip skirt, because you just can't beat a matching set. Even when you're not wearing it with the top, this skirt is ultra versatile.

Madewell

Promising review: "Such a nice versatile piece. Fabric is really nice and the fit is great. Nice flow. I’m 5’5” and it hits nicely." —Boston Erica

Price: $115.50 (originally $128; available in sizes 00–16 and in three colors)

6. A denim scoop-neck vest if retro style is your thing, and you want to meet your new favorite piece that'll be a staple in your outfit rotation.

Madewell

Promising review: "Wore this vest with a similar color denim bell bottom. It was giving Stagecoach, but works for a nice dinner date." —Tizzzina

Price: $98 (available in sizes 00–16)

7. A textured knit tank to amp up your sightseeing look. Wear this with a pair of shorts and tennis shoes, and you've got yourself an outfit you'll want to take pics in while standing in front of the colosseums in Rome.

Madewell

Price: $49.99+ (originally $78; available in sizes XXS–3X and two styles)

8. A puff-sleeve midi dress that's simply made for wearing to a harborside dinner in St. Tropez or happy hour at your favorite bar in Charleston.

Madewell

Promising review: "I LOVE this dress. It is so darn cute and makes me feel like Snow White. I love the longer torso; it really makes the proportions of this dress perfect. Since the bodice is fully smocked, the sizing is pretty flexible. I am super curvy and got an XL."  —WaveD

Price: $99.99+ (originally $148; available in sizes XXS–3X and in two colors)

9. Or a cap-sleeve floral midi dress for showing off just how stylish you are as you head for tapas at that one restaurant that has been all over your TikTok FYP ever since you booked your dream trip to Mallorca.

Madewell

Promising review: "I bought this dress last week for an upcoming graduation and absolutely love it — have already worn it. The fit is great, it’s comfortable enough to wear all day without losing shape."  —Emiemart

Price: $99.99 (originally $158; available in sizes 00–16)

10. A lightweight and comfortable bell-sleeve linen top for adding a subtle '70s vibe to your Greek getaway. If there's one way to channel your inner Donna Sheridan, it's by adding bell sleeves to your wardrobe.

Madewell

Promising review: "I've absolutely loved this top, and have gotten tons of compliments on it. The material is so pleasing! I ended up with a medium, and I'm pretty tall, so I could see it being a little long on someone shorter than me." —SarahGenevieve

Price: $86.40 (originally $96; available in sizes XS–3XL)

11. A side-cinched muscle tee that *feels* as soft as pajamas but will elevate your outfit for any occasion thanks to its chic cut and black-hem detailing.

Madewell

Promising review: "Such a beautiful top! I love how simple yet classy that it is. The material is so soft and breathable. Perfect for hot summer days. The white with the little black stitching is perfect!" —Mamasaures

Price: $45.99+ (originally $52; available in sizes XXS–XXL and in four colors)

12. An easy breezy boat-neck tank complete with airy side slits, so you can stay cool on your UK road trip when the weather reaches 78 degrees but British heat hits different and it feels like you're burning in the furnace of hell.

Madewell

Promising review: "I super love the fit and it looks so chic!!!!" —Isabella

Price: $19.99+ (originally $42; available in sizes XXS–XXL and in three colors)

13. A ribbed lace-up tee that will probably become your new favorite item of clothing in your suitcase. Pair it with skirts, shorts, jeans, and beyond.

Madewell

Promising review: "It is the first one out of my closet after washing. You can dress it up or down, and it is very comfortable!" —Runner

Price: $28.99+ (originally $45+; available in sizes XXS–XXL and in four styles)

14. A waffle-knit long-sleeve crewneck tee to toss on over your outfit when the sea breeze kicks in and you're a little bit chilly. There's nothing better than a sunrise walk along the beach.

Madewell

Promising review: "Love that it’s comfy and loose, yet provides a great shape. The red is perfect, and I wish they would make more bright colors for this top." —Cute Comfort

Price: $19.99+ (originally $68, available in sizes XXS–XXL and in six colors)

15. A pair of pleated trouser shorts, because sometimes you want a change from your denim shorts. These ones give a structured finish and will look great during the day or at night.

Madewell

Promising review: "Bought these shorts for work over the summer, they fit great and are very cute!" —Mads

Price: $61.99 (originally $78; available in sizes 00–16 and in three styles)

16. A perfect cotton crewneck tee that is so comfy and stylish, I won't blame you if you buy one in every color and pattern (in fact, I'd applaud you).

Madewell

Promising review: "This tee has such a nice cut!! I did decide to size up for a roomier fit, but have been reaching for this piece over and over." —Robyn98

Price: $19.99+ (originally $42, available in sizes XXS–XXL, 1X–4X in select styles, and in nine styles)

17. A ballerina-esque midi dress because it's *the* silhouette of the season for less $$$ than the higher-end versions. You'll be looking ~on pointe~ all summer long.

Madewell

Promising review: "Recently bought this dress on a whim and have ZERO regrets! It is so comfortable and incredibly stylish, I have gotten soooo many compliments on it already. Easy to dress up and dress down, this is the versatile dress of your dreams. Oh, and it has pockets. 🥲" —Dress Obsessed

Price: $154.99+ ($168.99; available in sizes 00–16, petite sizes, and in two colors)

18. A 100% hemp tie-front top that's neutral enough to be worn over and over again with whatever bottoms you packed, but unique enough to elevate any look (and while giving you some cinching action in the process).

Madewell

Price: $99.90 (originally $111, available in sizes XS–XXXL)

19. A one-shoulder swimsuit that's definitely a swimsuit *made* for an Instagram pic or two, thanks to its eye-catching cutout back and slightly metallic material.

Madewell

Price: $198 (available in sizes XS–XL)

20. A pair of pull-on culottes for a chic, laid-back look that screams, "I'm heading to the south of France for vacation, au revoir."

Madewell

Price: $98 (available in sizes XS–XXL and in two colors)

21. An absolutely perfect patterned slip dress that you'll want to ~slip~ into time and time again, even if it's just to strut down to the beach from your hotel.

Madewell

Promising review: "Better than expected! I saw this dress first in an email, I couldn’t stop thinking about it! Honestly, the fit is perfect. Honestly, it's like it was made to fit me. The open back is beautiful, the material is soft and light, and it can be dressed up or down." —Kbauer

Price: $198 (available in sizes 00–16)

22. A pair of wide-leg linen pants so free and flowy, you'll be forgiven for thinking that you forgot to put pants on before leaving your hotel room.

Madewell

Promising review: "I saw these pants in the store and had been looking for a jeans substitute. They have great lines, and I love the back pockets. The fabric is a nice weight and sort of a chambray feel. Great with little tops, no belt needed. I will be wearing these all summer!"  —Gigi

Price: $72.50+ (originally $118; available in sizes 00–16, petite and tall sizes, and in five colors)

23. And a matching shirred linen shirt to complete a vacay-worthy look everyone will be jealous of, *and* will be perfect for mixing and matching with the other things in your suitcase.

Madewell

Promising review: "LOVE this linen too! Lies perfectly. Pulls together any outfit —effortlessly chic! Please make it in other colors!!" —Linenlover

Price: $84.50+ (originally $98; available in sizes XXS–XXL and in three colors)

24. A square-neck romper for the girlies who *know* the struggle of wearing a short dress when a strong gust of wind comes along. This romper looks like a mini dress, but the flowy shorts mean you won't flash everyone when it's breezy.

Madewell

Promising review: "I’m obsessed with this romper! It’s true to size, the fabric is great, and the overall fit is perfect! It’s not too short, and I’m tall. Please make this exact romper in more colors!"  —ShelliG

Price: $118 (available in sizes 00–16)

25. An off-the-shoulder dress with a smocked bodice because nothing says “summer is here” like getting your shoulders out in some sunshine.

Madewell

Price: $169.99 (originally $278; available in sizes 00–16)

26. A swishy tie-shoulder midi dress (because you can never bring too many dresses on vacation, right?) to keep you looking *and* feeling super cool, even as the temps get hotter and hotter.

Madewell

Promising review: "This dress is such a great summer staple. Stretchy and comfortable, I can see myself wearing it all season for work and the weekends."  —Sleary

Price: $109.99 (originally $158; available in sizes 00–16)

27. And finally, a simple and elegant button-down to give any look a ~professional~ vibe, even though your out of office is ON.

Madewell

Promising review: "I bought this blouse in store and absolutely love the fit, the look, and the versatility. It is slightly cropped, and the side cutouts do come up a bit, but it looks awesome with high-waisted bottoms. I purchased my regular size."  —Annie O

Price: $88 (available in sizes 00–16)

The reviews for this post have been edited for length and clarity.