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8 Times Hailey Baldwin Gave Us Serious Style Envy

8 Times Hailey Baldwin Gave Us Serious Style Envy
31 Start slideshow
Photo: Gotham/GC Images/Getty Images

You may have noticed we have sort of a thing for Hailey Baldwin, whether that means following along with her more outré fashion choices—looking at you, $1,200 flannel shirt and windbreaker-dresses—or chronicling her beauty evolution. What can we say? The 21-year-old model and Tommy Hilfiger ambassador has a way of standing out from the crowd and getting us talking with her always-unexpected style choices—and that’s a trend that’s sure to continue as her star keeps rising.

Of course, while Baldwin’s reputation for pushing the limits of fashion makes her fun to watch, you may think you can’t actually pull off some of the combinations she regularly makes work. Well, we respectfully disagree. Some of her greatest looks are actually the simplest to copy—like her genius way of wearing PJs all day, or the fashion-forward minidresses that are actually so easy to wear with a couple well-chosen accessories.

Don’t believe us? We’ll prove it. Ahead, we picked our 8 favorite Hailey Baldwin outfits ever, and broke them down into pieces you can shop right now. We’re still working on looking as amazing as she does in a windbreaker dress, but as soon as we crack that, we’ll let you know.

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Summer Whites
Summer Whites

Hailey Baldwin was spotted last month in New York City wearing this ideal summer 'fit: a cute striped tee and super-chic wide-leg trousers with clean white sneaks to match. (You have our permission to wear white past Labor Day for this one.)

Photo: Gotham/GC Images/Getty Images
The Striped Tee
The Striped Tee

Madewell Mockneck Shirttail Tee in Stripe, $45 at Madewell

Photo: Madewell
The Wide-Leg White Trouser
The Wide-Leg White Trouser

Odeeh Wide Leg Trousers, $281 at Farfetch

Photo: Farfetch
The Gold Hoops
The Gold Hoops

Cinco Astrid Earrings, $64 at Cinco

Photo: Cinco
All-Day PJs
All-Day PJs

We love nothing more than lazing in bed all day on a Sunday. But if we absolutely must venture out, best to do it in a chic pajama shirt with contrast piping, like Baldwin did here.

Photo: Alo Ceballos/GC Images/Getty Images
Tommy Hilfiger Girlfriend Shirt
The Oversized White Shirt

Tommy Icons Girlfriend Shirt, $99.50 at Tommy Hilfiger

Photo: Tommy Hilfiger
The Light-Wash Jean
The Light-Wash Jean

3x1 W4 Colette Slim Crop Colbey, $265 at 3x1

Photo: 3x1
Dreamy Blue Dress
Dreamy Blue Dress

We're still high-key obsessed with this dreamy, layered baby-blue dress Baldwin wore back in 2017—she made it even cooler with chic neutral accessories.

Photo: Jackson Lee/GC Images/Getty Images
The Blue Dress
The Blue Dress

Ganni Faulkner Maxi Dress, $250 at Ganni

Photo: Ganni
The Mini Bag
The Mini Bag

Building Block Drum Bag in Veg Tan, $595 at Building Block

Photo: Building Block
The Sock Boot
The Sock Boot

Rag & Bone Ellis Stretch-Knit Sock Boots, $595 at Net-A-Porter

Photo: Net-A-Porter
Collegiate Chic
Collegiate Chic

There's something about an oversized cable-knit that feels so very homecoming weekend. It's basically fall in sweater form. We love how Baldwin adds some edge to the preppy vibe with those optic white boots.

Photo: Jackson Lee/GC Images/Getty Images
The Cable-Knit Sweater
The Cable-Knit Sweater

Tommy Icons Crest Sweater, $225 at Tommy Hilfiger

Photo: Tommy Hilfiger
The Denim Skirt
The Denim Skirt

Madewell Rigid Denim Straight Mini Skirt, $69.50 at Madewell

Photo: Madewell
The White Boots
The White Boots

Marc Ellis Pointed Toe Ankle Boots, $191 at Farfetch

Photo: Farfetch
Gala Girl
Gala Girl

Baldwin wore maybe her most elegant look yet to last fall's Hammer Museum Gala. This sleek black turtleneck, full tea-length skirt, and simple black heels are the definition of pared-down, unfussy chic.

Photo: Axelle/Bauer-Griffin/FilmMagic/Getty Images
The Sleek Black Sweater
The Sleek Black Sweater

Forever 21 Sweater-Knit Wrap Top, $15.90 at Forever 21

Photo: Forever 21
The Striped Midi Skirt
The Striped Midi Skirt

Valentino High-Rise Chevron-Striped Pleated Jersey Skirt, $1,490 at Matches Fashion

Photo: Matches Fashion
The Chic Black Shoe
The Chic Black Shoe

Who What Wear Annie Satin Tassel Pointed Mules, $37.99 at Target

Photo: Target
No Sweat
No Sweat

Baldwin excels at streetwear-infused outfits that may or may not actually make it to the gym (but look really cool regardless). Here, she balances a teeny crop top with '90s-style oversized camo pants, a cozy jacket, and paparazzi-blocking black shades.

Photo: Gotham/GC Images/Getty Images
The White Sports Bra
The White Sports Bra

Under Armour Armour Mid Sports Bra, $24.99 at Under Armour

Photo: Under Armour
The Camo Joggers
The Camo Joggers

Pam and Gela Bronze Stripe Camo Sweatpants, $265 at Shopbop

Photo: Shopbop
The Extreme Wayfarers
The Extreme Wayfarers

V by Vye Alter Ego Sunglasses, $13 at V by Vye

Photo: V by Vye
Off-White
Off-White

Would you think to wear an off-shoulder, off-white shirt with easy gray joggers and sky-high blue heels out clubbing? Neither would we. But Baldwin did, and as always, the unexpected mix looks amazing on her. Take that, sea of body-con.

Photo: Ricky Vigil M/GC Images/Getty Images
The Off-Shoulder Shirt
The Off-Shoulder Shirt

Rosie Assoulin The Potato Chip Top, $1,195 at Rosie Assoulin

Photo: Rosie Assoulin
The Gray Sweats
The Gray Sweats

Tommy Icons Joggers, $99.50 at Tommy Hilfiger

Photo: Tommy Hilfiger
The Blue Pumps
The Blue Pumps

Marc Fisher Doreny Bow Suede Pump, $50 at Nordstrom Rack

Photo: Nordstrom Rack
Little Black Dress (and Boots)
Little Black Dress (and Boots)

Baldwin toughens up a retro-inspired black minidress with the sleekest possible version of a combat boot, and her signature black shades. Add tights and this is you all fall.

Photo: Bauer-Griffin/GC Images/Getty Images
The Printed Minidress
The Printed Minidress

Rouje Gabinette Dress, $192 at Rouje

Photo: Rouje
The Slim Combat Boot
The Slim Combat Boot

The Row Fara Lace-Up Suede Combat Boot, $1,295 at Bergdorf Goodman

Photo: Bergdorf Goodman
The Black Shades
The Black Shades

V by Vye Rumour Sunglasses, $13 at V by Vye

Photo: V by Vye

Next slideshow starts in 10s

Every Stunning Beauty Look at the 2018 Primetime Emmy Awards

Every Stunning Beauty Look at
the 2018 Primetime Emmy Awards
  • Summer Whites
  • The Striped Tee
  • The Wide-Leg White Trouser
  • The Gold Hoops
  • All-Day PJs
  • Tommy Hilfiger Girlfriend Shirt
  • The Light-Wash Jean
  • Dreamy Blue Dress
  • The Blue Dress
  • The Mini Bag
  • The Sock Boot
  • Collegiate Chic
  • The Cable-Knit Sweater
  • The Denim Skirt
  • The White Boots
  • Gala Girl
  • The Sleek Black Sweater
  • The Striped Midi Skirt
  • The Chic Black Shoe
  • No Sweat
  • The White Sports Bra
  • The Camo Joggers
  • The Extreme Wayfarers
  • Off-White
  • The Off-Shoulder Shirt
  • The Gray Sweats
  • The Blue Pumps
  • Little Black Dress (and Boots)
  • The Printed Minidress
  • The Slim Combat Boot
  • The Black Shades

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