Although I love a good pair of jeans, I'll pick a breezy summer dress to wear over denim any day. Now that the weather is reaching the high 70s in the city, I'm leaning more and more into the surge of summer dresses that have been inundating my heart and mind. If you're an impulsive shopper like me, it's easy to snag a super-cute, ultra-trendy summer dress style that you've seen on at least five celebrities. Let's be real, though. Timeless, chic summer dresses are where it's at, especially ones easy on the eyes and wallet.
Below, browse 40 dresses I can't stop thinking about, all ringing in under $100. Ahead of the official start of summer, aka Memorial Day weekend, these are the cutest clothing items you need the most. Happy shopping!
Abercrombie & Fitch
Slip Midi Dress
Open Edit
Ribbed Midi Tank Dress
This one is a best seller for a reason—it goes with everything.
Mango
Puffed Sleeves Dress
This pick instantly transports me to the South of France.
Bp
Shirred Puff Sleeve Prairie Dress
You can always use a cute LBD in your summer rotation.
Sndys
Tahlia Dress
One word: Chic.
French Connection
Rassia Sleeveless Cotton Knit Dress
The high neckline on this dress makes it feel ultra elevated while still making a statement with a pop of color.
H&M
Off-the-Shoulder Cotton Dress
Wait, I think I just found the holy grail of all white maxi dresses.
English Factory
Ruffled Detail Mini Dress
The ruched bodice on this mini makes it extra comfy.
Eloquii
One-Shoulder Cutout Waist Maxi Dress
For the people who are dead set on living their Hot Girl Summer life.
River Island
Metallic Rib Body-Con Dress
Little details on knit dresses—like these O rings—can transform anything from boring to brilliant.
Zara
Linen Blend Strappy Dress
At 50% off, this Zara maxi is an absolute steal.
Hansen & Gretel
Evelyn Dress
Although there's only one size left in this dress, I'm patiently waiting for it to arrive in the mail after I already hit buy.
Astr the Label
Delancy Dress
Not a want, but a need.
Hansen & Gretel
Adrienne Dress
No need for a bikini—this one already has one built in.
H&M
Oversized One-Shoulder Dress
This dress looks 10 times more expensive than it actually is.
H&M
Flounce-Trimmed Dress
Match with your limoncello this summer.
Reformation Active
Milana Ecomove Dress
Channel your inner Meredith Blake with this ultra-cute activewear look perfect for running errands in.
Z Supply
Brayden Dress
I can never say no to a knit dress.
Staud
Astro Dress
Staud for less than $100? Sign me up.
Zara
Openwork Dress with Metallic Thread
I can get behind the sheer trend this year.
Fraiche by J
Long Sleeve Tie Front Dress
This dress is a classic for a reason.
J.Crew
Gwyneth V-Neck Cupro-Blend Slip Dress
BRB, transforming the rest of my closet to match this dreamy lilac hue.
English Factory
Mixed Media Pleated Mini Dress
A preppy pick for those late summer evenings on the New England coast.
H&M
Crochet-Look Dress
Crotchet maxi dresses may be one of the best dress trends to emerge from this year.
Rumer
Kimberley Sheath Maxi Dress
Ideal for any summer weddings you have.
Reformation
Kienna Linen Dress
Reformation's linen is simply unmatched.
Zara
Satin Effect Dress
This color is living rent-free in my mind as of late.
Moon River
Stripe One-Shoulder Cutout Midi Dress
Adorable.
Zara
Cut-Out Midi Dress
Framboise fantasy.
Mango
Straight Suede Dress
This mod-looking dress looks like it was taken straight off the set of Daisy Jones & The Six.
Peixoto
Serena Dress
Weird tan lines aside, this is a major slay.
Zara
Knit Midi Dress
Zara's knitted dresses are some of the comfiest on the market.
H&M
Bandeau Dress
Style this dress up or down with a pair of heeled sandals and chunky gold jewelry or your favorite running shoes and an oversize poplin dress shirt.
H&M
Crochet-Look Halterneck Dress
This pick is already en route to me.
H&M
Tie-Belt Dress With Buttons
I didn't think I would love zebra print this much in 2023, yet here we are.
Free People
Vintage Summer Midi Dress
This chocolate color is divine.
H&M
Pleated Tunic Dress
No need to pack a steamer on your summer travels abroad. This dress already comes pre-wrinkled and is all the more effortlessly chic because of it.
Mango
Stripe Puff Sleeve Dress
This butter-yellow dress from Mango is by far one of my favorites on the list.
Reformation
Aubree Linen Dress
Green with envy for whoever snags this dress before I do.
Ana Escalante is an award-winning journalist and Gen Z editor known for her sharp takes on fashion and culture. She’s covered everything from Copenhagen Fashion Week to Roe v. Wade protests as the Editorial Assistant at Glamour after earning her journalism degree at the University of Florida in 2021. At Who What Wear, Ana mixes wit with unapologetic commentary in long-form fashion and beauty content, creating pieces that resonate with a digital-first generation. If it’s smart, snarky, and unexpected, chances are her name’s on it.