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.
-
From Engagement to Holiday Parties, My Closet Is in Need of Some Fancy Dresses—32 Chic Options I'm Eyeing
Here are the standouts.
-
A First-of-Its-Kind Collaboration: Introducing New Balance x TAG Heuer
"It's a true partnership—something that we've been building over time together."
-
10 Trends Set to Define Spring 2026 Fashion
Explore our deep dive into the top trends from the runways.
-
Step Aside, Butter Yellow, Burgundy, and Baby Pink—2026's It Color Has Just Arrived
Refreshingly good.
-
Walk a Mile in My Shoes—My Honest Review of the Nike V2K Sneakers
Are they worth it? Find out.
-
This Is the Luxe Fall Shoe Trend Every Fashion Person Is Already Wearing on Repeat
Count these inspo pics as proof.
-
I'm Seeing This Quietly Chic Flat-Shoe Style Paired With Outfits Everywhere This Fall
There are endless ways to wear it.
-
The State of Style in 2026: Color, Prep, and the End of Quiet Luxury
Discover the global influences that are shaping modern fashion trends for 2025 and 2026.