Summer in the city means one thing: dress season! When temperatures rise, New York’s fashion mavens know exactly how to transform delicate frocks into street-style gold. I’ve spent years studying their effortlessly cool approach to summer dressing, and now I’m spilling all their secrets to help you nail that coveted Manhattan vibe.
1. Layer with an oversized blazer
Nothing screams New York cool like throwing an oversized blazer over a floaty summer dress. The unexpected contrast between structured masculinity and feminine flounce creates that perfect tension we city girls live for. Grab your boyfriend’s jacket or size up—the boxier the better!
2. Add chunky combat boots
While tourists pair their dresses with predictable sandals, true NYC girls know the power of juxtaposition. Heavy-duty combat boots under a floaty dress create that perfect downtown edge we crave. Doc Martens or Prada—pick your poison and stomp accordingly!
3. Belt it with something unexpected
Forget those flimsy belts that came with your dress! Hunt down vintage leather motorcycle straps, repurposed scarves, or even men’s ties to cinch that waist. Yesterday I used a western-style concho belt over my prairie dress and received compliments all day in SoHo.
4. Layer over a fitted tee
Though counterintuitive, slipping a fitted tee under that spaghetti-strap dress instantly transforms it from basic brunch to gallery-hopping cool. White works, but true downtown girls opt for vintage band shirts or striped marinières. I’ve worn this combo from morning meetings to midnight cocktails!
5. Mix in vintage sportswear
Where tourists fail, New Yorkers triumph by fearlessly mixing delicate dresses with sporty elements. Think vintage Yankees caps, retro track jackets, or basketball sneakers with prairie dresses. The high-low contrast feels deliberately undone—exactly what we’re aiming for!
6. Embrace clashing prints
Forget matching! When I’m heading to an art opening in Chelsea, I deliberately clash my floral dress with leopard accessories or striped layers. The secret? Keep silhouettes simple when prints go wild. The more seemingly mismatched, the more intentional it appears!
7. Add architectural jewelry
Whereas tourists pile on dainty chains, Manhattan’s fashion set opts for one statement piece with architectural presence. I swear by sculptural cuffs or geometric earrings from local designers. These conversation-starting pieces transform even H&M dresses into high fashion territory!
8. Throw on a leather jacket
However sweltering the subway platform gets, true New Yorkers keep their leather jackets handy. Nothing toughens up a sweet sundress faster than worn-in black leather. My vintage Schott has accompanied countless summer dresses from rooftop parties to late-night diners!
9. Mix high and low pieces
If you spot a woman pairing a Target dress with Prada loafers on the L train, you’ve witnessed peak New York styling. The deliberate high-low mix signals insider knowledge. Last week I wore a $30 sundress with vintage Ferragamo shoes, and nobody could tell which was which!
10. Layer unconventional socks
Forget bare legs! New York’s fashion-forward set pairs summer dresses with unexpected hosiery—think ribbed athletic socks with loafers, sheer polka dots with heels, or even colorful compression socks with chunky sandals. I’m currently obsessed with my neon crew socks under dresses!
11. Tie a bandana strategically
Whether knotted as a choker, wrapped around a wrist, or tied to a bag strap, bandanas add instant downtown credibility to any summer dress. Vintage ones from thrift stores carry the most cachet. My collection ranges from faded Americana prints to psychedelic 70s patterns!
12. Wear unexpected layers underneath
Though tourists might gasp, cool New Yorkers layer mesh tops, ribbed tanks, or even swim tops under sheer summer dresses. The unexpected layering creates visual interest while maintaining that coveted nonchalant vibe. I’ve worn a sports bra under a gauzy dress and received countless compliments!
13. Anchor with chunky sneakers
Forget dainty flats—New York’s fashion crowd grounds ethereal dresses with substantial sneakers. Whether vintage Reeboks, chunky New Balance, or platform Converse, the contrast creates that perfect high-low tension. My go-to summer uniform is a slip dress with beat-up Asics!
14. Add a structural hat
While suburban America reaches for floppy sun hats, city girls opt for architectural headwear with attitude. Think structured bucket hats, baseball caps from obscure teams, or even vintage berets regardless of temperature. My Lack of Color bucket hat elevates even the simplest sundress!
15. Mix in workwear elements
Construction-inspired pieces add unexpected edge to feminine dresses. Think Carhartt jackets, utility vests, or mechanic-style shirts tied at the waist over flowy fabrics. My Dickies work shirt transforms my precious prairie dress into something infinitely cooler for weekend flea markets!
16. Pile on mixed-metal jewelry
Forget matching metals! NYC style mavens stack silver, gold, brass and copper with abandon. The trick? Wearing unexpected combinations that look collected over time rather than purchased as sets. My wrists feature everything from flea market finds to family heirlooms alongside summer dresses!