Wear This Classic, Chic Look on Repeat

Photo via: @speak_style

A great outfit is worthy of repetition and this street style look is one of those gems. We love this preppy yet relaxed look that’s easy to pull together, comfortable enough to wear anywhere and looks totally polished. Pair skinny black jeans with a simple sweater in a neutral tone and a plaid blazer. Add white sneakers to give it a relaxed vibe, and you’re good to go. Put this chic look together by shopping our top picks below.

We Love These Chic School Girl-Inspired Outfits

Photos via: @thestylestalkercom | @collagevintage2 | @laurencefortincote

This season's fashion month saw a lot of preppy styles emerge from our closets. Just take a look at Alexa Chung's high-collar lace blouse paired with platform Mary-Janes, or Laurence Fortin-Côté's additions of a chic headband and chunky Oxford shoes to an all-black outfit. Street style photographers Szymon Brzóska and Diego Anciano were sure to catch these trends. Take a peek at our favorite picks to copy the look below.

Don’t Get Dressed Without a Plaid Skirt in Your Closet

Photo via: @jennymwalton

Colder seasons and cozy plaid skirts go hand in hand and illustrator, designer, and style muse, Jenny Walton, proves the point in this ultra-chic outfit. We love her pairing of knee-high boots, pullover sweater, and cognac bag for an effortless take on this preppy pleated skirt style. Pick a plaid and your favorite skirt style, and mix it up with anything in your closet, from heels to blazers or even a leather jacket for an extra edge.

The Prettiest Tweed Skirts For a Preppy Fall

Photo via: Collage Vintage

One of our favorite fabric trends of the moment is tweed; a feminine, preppy texture that adds sass and nostalgia to every look. A tweed skirt will instantly elevate an outfit––whether it's paired with a turtleneck, button-down or silk blouse, making it an essential fall wardrobe piece. Wear yours with contrasting tops to get the street style look above.

9 Chevron Dresses That Aren't Cliché

Photo via: Style Du Monde

Chevron dresses used to be exclusive to preppy girls and sorority houses but lately, they've gotten a modern, sophisticated update. Look to these chevron options below—you won't be disappointed. From bright reds and silky fabrics, these are how you upgrade the classic.

The Madewell Pieces We Have Our Eye On This Winter

Photo via: Madewell

When it comes to preppy, peppy, and bright, Madewell is always in the forefront of our minds for winter dressing. From striped pullovers and turtleneck dresses to plaid coats and bucket bags, here are the items we'll be coveting this season.

Olivia Palermo Makes Us Want a Pleated Skirt

Photo via: Style Du Monde

No one does preppy, upper east side style quite like style icon Olivia Palermo. How do you give your midi skirt a polished overhaul? With pleats. After seeing this picture, we're ready to shop. Check out a few of our favorite pleated skirts.

How To Modernize A Traditionally Preppy Print

Photo via: Stylecaster

If you're feeling stuck in a winter vortex rut, opt for a checkered print. Although this pattern is traditionally preppy, there are ways to incorporate it in a chic, modern way. Add a beanie, belt it, and throw on some slingback heels or a funky boot.

18 Items From J.Crew We're Obsessing Over

Photo via: J.Crew

Preppy meets sleek sophistication at J.Crew, always. With their modernized staples, cozy basics, and vibrant fabrics, this brand remains a go-to for the fall and winter seasons. Whether you're searching for a relaxed topcoat, tartan skirts, or holiday-party-heels, they have got you covered. Check out the retailers most covetable pieces below.

How to Do The Preppy Chic Look in 2017

Photos via: Atlantic Pacific

Gone are the days when pink bermuda shorts, moose printed button ups, and whale-clad caps were the definitions of preppiness. Even J. Crew has moved past its standard yacht aesthetic for something a little chicer, a little more sophisticated. Blair knows how to do modern preppy the right way. She stunned in a striped off-the-shoulder top, Gucci belt, and khaki midi skirt.

Get the look:
+ ASOS Long Sleeve Body In Stripe
+ J. Crew Off-The-Shoulder Striped Shirt
+ Gucci GG Buckle Leather Belt
+ Fame And Partners The Marley Skirt
+ ASOS Zip And Pocket Midi Skirt

This Pleated Trench Coat Is A Dream

Photo via: J.Crew

Let's be honest—we all missed outerwear so, so much. And, when a brand comes along and knocks it out of the park, we just have to share. J.Crew is known for its preppy, whimsical basics, so of course, they turned a regular ole trench coat into one of our dreams. This trench is pleated, water-resistant, and made of the softest cotton.

Get the look:
+ Pleated Trench Coat
+ New Perfect Shirt

11 Pieces From J.Crew That You Will Literally Obsess Over

Photo via: J.Crew

The 'literally obsess' in the title is no understatement. J.Crew has always been a haven for luxe basics, fun vibrant colors and unique preppy (but not too yatchy) options. Recently, they've released some summer pieces that can amplify your entire wardrobe this summer. From striped tie-neck tops to gingham midi dresses, check out these must-have pieces.

Get the look:

Under $200: Gingham Tie Sleeve Shirt

Photo via: Urban Outfitters

If you haven't been under a rock and have been keeping up with the latest and greatest trends, then we're sure you've spotted the gingham print all around. The pretty fabric/print that once was exclusive to preppy brands, has gotten a streetwear rebrand. This red gingham tie-sleeve shirt is a perfect way to push into this popular trend. Wear it with vintage-inspired cropped jeans and strappy sandals.

Get the look:
+ Style Mafia Gingham Tie Sleeve Shirt
+ Levi's Wedgie High-Rise Jean
+ Urban Outfitters Strappy Suede Sandals

How To Toughen Up A Gingham Print Shirt

Photo via: @beigerenegade

Jiawa Liu proves that a gingham shirt doesn't necessarily have to look and feel preppy by toughening it up with a black grommet-detailed skirt, a chic grey Chloé bag and white sneakers. The true styling standout of her outfit though is how she wore the Tibi shirt unbuttoned and draped off one of her shoulders.

Get the look:
+ Tibi Gingham Utility Blouse
+ Paige Mya Gingham Shirt
+ Chloé Faye Leather And Suede Bag
+ Rebecca Minkoff Grommet Skirt
+ Kensie Grommet Pencil Skirt

3 Fashion Bloggers, 3 Striped Dresses

Photos via: Sequins And Stripes | We're Not Exclusive | The Fancy Pants Report

Some things never go out of style and stripes are one of them. Because of their extremely versatile and universal appeal, stripes can adorn just about anything and we'd be willing to purchase it. One blogger styled hers with a preppy flair by adding in pieces like a beach hat, wedges and a leather crossbody bag. I paired mine with fringed mules and an embroidered clutch. Last but certainly not least, this lady wore a striped tank dress with a denim jacket tied around the waist and added in a pair of crisp white sneakers. Three dresses, one uber-trend, a million more ways to wear it.

Get the look:

See How To Wear An Off-The-Shoulder Jumpsuit Like Jenna Lyons

Photo via: Popsugar

Jenna Lyons is one of few designers who have essentially, changed the way we chose to dress. She altered the image we think of when the word, 'preppy' comes into play by mixing and matching, combining geek with chic and adding in luxury to a beloved brand. Above, she shows off some sun-tanned skin in a plaid, off-the-shoulder jumpsuit with contrasting belt and sandals.

Get the look:

How to Style a Shirtdress for Summer

Photos via: My Domaine | Vogue

Oversized, perfectly tailored or asymmetrical. Whatever the structure of this piece, the shirtdress is basically the most versatile (and comfortable) summer staple of all time. Shirt dresses are essentially longer versions of the classic button-down and will equally prove their worth. Whether you are sporty, preppy or the most tomboy-ish of women, this piece works for everyone and every style. Wear it like Rihanna with an oversized tote and sneakers or go girly with a pleated, shorter version like Olivia Palermo. Also, what more could we want for summer than a forgiving, loose and lightweight dress?

Get the look:
+ DKNY Long Sleeve Shirtdress
+ Kenzo K-Lace Sneakers
+ Brock Collection Flared Shirt Dress
+ Polo Ralph Lauren Poplin Shirt Dress
+ Aquazarra Sexy Thing Suede Heels

Model-Off-Duty Style: Steal Caroline Brasch Nielsen's Preppy Look

Photos via: Harper's Bazaar | Highsnobiety

Caroline Brasch Nielsen is hands down one of the best models out there with great personal style. I had these street style shots filed away for spring and summer, so what better time than now to use her preppy look as inspiration!

Get the look:
+ Equipment Brett Blouse in Klein Blue
+ Donna Sharp Deidre Convertible Crossbody Wallet
+ Farrow Chloe Skirt
+ The Laden Showroom X I Love Friday Raw Hem Denim Midi Skirt
+ Cole Haan Mesi Leather Sandal Slide (also here)

Spring Neutrals | Shopbop Sale

Getting a jump start on my spring shopping with the Shopbop sale (up to 25% off!). As you can tell, I'm currently more obsessed than ever with neutrals...

1. T by Alexander Wang Striped Rayon Linen Tee
2. Oliveve Anastasia Clutch
3. Saint Laurent Classic Preppy Rounded Sunglasses
4. La Perla Studio La Perla Rosa Triangle Bra
5. Rag & Bone Summer Fedora
6. Nixon Kensington Leather Watch
7. Rifle Paper Co Garance Dore Collection Assorted Girls Greeting Card Set
8. Schutz Dubianna Lace Up Sandals

Preppy Chic

Photos via: J.Crew

Loving Behati Prinsloo in this perfect preppy chic look with a gold buttoned blazer, classic white button-down shirt, cropped skinny jeans and embroidered loafers.

Get the look:
+ Bailey for J.Crew Felt Hat
+ J.Crew Navy Schoolboy Blazer
+ Gap Fitted Boyfriend Oxford Shirt
+ Siwy Hannah Jeans
+ Ilenia P. Moccasins