23 Pretty Spring Dresses New Yorkers Will Wear With Sneakers and Flats—Trust Me

You know it's really spring when all the pretty dresses start to drop. In New York, where the temperatures are up and down until sometime in mid-May, these dresses will be worn with blazers, trench coats, and cashmere sweaters until further notice. True to NY style, the most coveted dresses in the city will be those that pair perfectly with the chic flat shoes New Yorkers wear on repeat.
This season's dress trends are delightfully wearable. All shades of brown and buttery yellow are dominating our palettes, drop waists still feel chic and effortless, and '90s-inspired florals feel as good dressed up as they do with white tennis shoes. Speaking of footwear, there's lots to report: Brown suede, having conquered our winter footwear, is coming for our strappy sandals. Soft loafers are your shortcut to a rich-looking spring look. Mesh and perforated flats—love 'em or hate 'em—are back. Also, I remain convinced that trendy, bright sneakers that seemingly go with nothing actually go with everything. I could have shared 100 options that deserve your attention, but I've managed to draw the line at just 23 of the best dresses and 11 pairs of flat shoes that are ready to mix and match for some excellent spring outfits.
Shop spring dresses:
Shop stylish flats:

Natalie Cantell is an NYC-based style director, creative consultant, and fashion editor, who regularly contributes from Paris. She was the executive director of Who What Wear and Marie Claire’s brand studio until 2023, and now freelances globally on shoots, stories, and special projects.
-
I'm Basically My Sister's Personal Stylist—36 Chic, Summer-Ready Zara Pieces I'm Sending Her Way
Plus, some hot new arrivals.
-
I'm a Shopping Editor—These 31 Under-$50 Amazon Finds Are Giving Main Character Energy
These were really hard not to gatekeep.
-
The Best Under-$400 Linen Dresses From Revolve, Shopbop, and Net-a-Porter
A summer must-have.
-
I Shop for a Living, and These Are the 15 Pretty Nordstrom Fashion and Beauty Finds in My Cart RN
Lace-trim skirts, shimmery eye shadows, and more.
-
Jacquemus Just Declared That This Subtle Style Accent Will Be Just as Popular in Summer 2026
The small detail creates a lasting impact.
-
Hold the Sneakers—This Is the Classy Flat-Shoe Style French Women Wear With 3 Different Casual Pants
The chicest look.
-
These $60 Flats Everyone Will Wear With Shorts Are About to Go Viral
Spoiler: They're on sale.
-
Kendall Jenner Wore Capris With the Only Shoe Trend Worse for Airport Security Than Flip-Flops
Risky but chic.