We’re calling it now: If there’s one hero piece you’ll reach for this coming season, it’s an off-duty pinafore dress with elevated schoolgirl appeal. ‘Cuz what’s not to love about a free-wheelin’ denim or corduroy overall dress that’s the very definition of comfort? For a Blair Waldorf-style look that’s so RN, coordinate your newly acquired pinafore dress with a bow-neck blouse (or crisp button-down) and heeled loafers. Or ditch the goody-two-shoes image altogether by teaming your thrift store denim patchwork jumper with a playful summer crop top and Chuck Taylors. Your move. It doesn’t matter where your style sensibilities reside — this is one fall must-have that will always do you right. Scroll down for 13 show-stopping ways to style your fave pinafore dress for back to school and beyond.
1. Golden by TNA Sieren Top ($75) + Boohoo Bree Ombre Denim Pinafore Dress ($18): Cue the half bun and Kylie Jenner-inspired swagger — this low-key pairing is made for girls who just wanna have fun. While the pink and blue ombre pinafore dress calls to mind summer sweet treats, the hippy-chic crop top is ready to conquer festival grounds. Pair the two together alongside an edgy leather backpack and retro metal rim sunnies for instant style cred.
How to Style a Denim Dungaree Pinafore Dress
2. Topshop Petite Blush Floral Bardot Top ($50) + Boohoo Daisy White Denim Dungaree Pinafore Dress ($35): Go ahead and kill two birds (or shall we say trends) with one stone by investing in a dungaree style dress and cold-shoulder top that demands attention. Better yet, wear them together for a foolproof #OOTD that slays from a.m. to p.m. It’ll look easy-breezy for the classroom with some metallic Birks and sultry for a GNO (just add chandelier earrings!).
How to Style a Corduroy Pinafore Dress
3. TNA Rushmore Shirt ($65) + Mango Corduroy Pinafore Dress ($60): While the thought of wearing corduroy in this scorching heat may not be so desirable (thanks, but no thanks), it won’t be long before you’re embracing warmer layers. With ankle booties and a western-style flannel shirt in tow, it’s only a matter of time before you’re ready to take on crisp fall days. Pssst: Style this HR-approved pinafore for the boardroom with a collared shirt for a non-fussy look that works around the clock.
How to Style a Moto Pinafore Dress
4. Zara Sequined Patches Bodysuit ($23) + Topshop Moto Scoop Pocket Pini Dress ($66): Prim and proper, this denim moto pinafore dress is not. Break all the rules by styling it with a black bodysuit featuring sequined patches (yes, we’re dead serious) and a borrowed-from-the-boys baseball cap. While this come-hither look may not cut it for the classroom (or your nine-to-five, for that matter), it’s guaranteed to be a hit on the dance floor.
How to Style a Black Pinafore Dress
5. Mango Message T-Shirt ($16) + Front Row Shop Black Patch Pocket Overall Dress ($62): The countdown until the weekend starts NOW. Whether you’re suffering from a case of the Monday blues or it’s finally Thursday (and you’re inching that much closer to Fri-yay), consider this your unofficial cool girl-approved uniform. This black overall apron-style frock is the type of dress you can toss on without a second thought — and still look totally DDG. Round out your A+ getup with a statement-making t-shirt for the win!
How to Style a Gingham Pinafore Dress
6. Farrow Jordan Top in Ivory ($58) + Sea Gingham Pinafore Dress ($425): Tap into your schoolgirl sensibilities with this preppy navy and white gingham dress that can double for student teaching duties and a weekend in Montauk. Can you say #winning? To make it office-appropriate, layer it over this Parisian-chic sleeveless collared blouse and then slip into some sensible espadrilles for a getup that’s not dowdy in the least.
How to Style a Tasseled Pinafore Dress
7. Ganni Seymour Georgette Shirt ($135) + Zara Short Pinafore Dress With Tassels ($100): When in doubt, ask yourself — WWACD: What Would Alexa Chung Do? For a London look that exudes major confidence, a little black pinafore dress is where it’s at. This tasseled number can be layered over slacks for post-work networking events, paired with over-the-knee boots come fall or styled with an ultra-femme silk polka dot blouse. An effortless fedora and a chic lob may or may not be required for extra style points.
How to Style a Patchwork Pinafore Dress
8. Zara Short Zipped Bomber Jacket ($50) + Topshop Moto Patchwork Pinafore Dress ($70): Take it to the streets with this athleisure-inspired combo that’s tough-girl chic at its best. Proceed to pack on the ‘90s ‘tude with a stretchy tattoo choker and a chunky pair of jelly sandals. Take our word for it: You straight-up need a seasonless patchwork denim dress this versatile on standby. Not only does it look rad with a plain white tee, but it looks super fly with a metallic bomber for a night of barhopping or just playing it cool with your squad.
How to Style an Embroidered Denim Pinafore Dress
9. Mango Decorative Patches T-Shirt ($20) + Dorothy Perkins Denim Pinafore Dress ($59): What rules? You proudly march to the beat of your own drum and aren’t afraid of showing up to the boardroom (or your English lit class) in an embroidered denim dress with next-level appliqués. Because your boyfriend’s oversized white tee simply won’t do (not this go-around, anyway), this t-shirt embroidered with decorative patches (we’re dying over the “not afraid of my boss” one) is what brings the cool. Let’s hope a Lisa Frank-inspired fanny pack or Pokemon backpack aren’t too far behind.
How to Style a Faux Leather Pinafore Dress
10. Wood Wood Wednesday Sweatshirt ($233) + Mango Pockets Pinafore Dress ($80): Enter not-so-school-girl territory a la this fierce faux leather pinafore dress with major model-off-duty vibes. We think our favorite bad girl RiRi could definitely pull it off. For mornings when you can’t even, slip this wardrobe workhorse over a statement-making sweatshirt, and bam! You’re ready to roll with your squad, even if it’s just heading to brunch before exam week hits. Cool kicks and your vintage letterman jacket are non-negotiable as you continue to slay on (and off) the streets.
How to Style a White Bib Overall Dress
11. Zara Frilled Top ($50) + H&M Bib Overall Dress ($50): Run, don’t walk, to snag this perennial favorite LWP (little white pinafore) for every remaining summer #OOTD. It’s comfortable for sprinting across campus, yet still pulled-together enough for dinner and a movie. Speaking of date night with your boo, you best be throwing this frilly OTS chambray top into the mix along with some “ugly” flatforms.
How to Style a Badge Pinafore Dress
12. H&M Short Jersey Top ($13) + Boohoo Pandi Badge Pinafore Dress ($30): Keep a case of the first-day outfit blahs away with this eclectic-chic badge pinafore dress that could serve double duty for the classroom (we’re looking at you, hip kindergarten teachers!) or a rock concert. Going hand-in-hand with your combat boots and hoop earrings, this striped jersey mock turtleneck is this close to making you ditch your good-girl image.
How to Style a Button-Front Pinafore Dress
13. The Great Striped Cotton-Jersey T-Shirt ($105) + H&M Denim Bib Overall Dress ($35): Remember that cute denim button-front pinafore dress you wore religiously with pigtails all through grade school? Yeah, it’s officially considered cool again. Take it from your kid sister — a denim pinafore dress (complete with suspenders and deep pockets, no less!) is guaranteed to earn you style-MVP status. Toss it on with a vintage striped tee and white tennies, and you’ll be walking around campus like a boss.
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