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.
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