How to Wear Flat Shoes With Dresses, Skirts, and Jeans This Fall 2025

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Knowing how to wear flat shoes stylishly is the sign of a true fashion pro. After all, who wouldn’t want to wear looks that are just as comfortable as they are fashionable and chic? Practical footwear doesn’t have to be a secondary alternative to heels—in fact, your flats can be a versatile and sophisticated resource that elevates any outfit.

Whether your personal style favors classic loafers, sleek knee-high boots, minimalist ballet flats, or the latest It sneakers, there are so many flat shoe options that allow for looks that are modern, functional, and even high-fashion. So below, find some ideas and practical tips for how to wear flat shoes with dresses, skirts, and jeans the way the fashion pros do.

Flat shoes with dressesDresses are a closet staple in fall because they work so well with transitional weather, when the days are still warm but the evenings are cool. It’s so easy to adapt your look to whatever situation or temperature with another light layer and the right accessories.

Midi-dress and ballet flats

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Pairing a flowing midi-dress with slim-toe ballet flats creates a feminine and comfortable look that’s perfect for the office, dinner with friends, or even a casual outing depending on the dress. This fall, look for dresses in earthy or neutral tones—think browns, mossy greens, beige, black, or gray—that will suit an autumnal palette, with flat shoes with metallic, velvet, or patent leather detail in a complementary color.

Faithful Brigitte Midi-Dress

Larroudé Verona Ballet Flats

Shirtdress and loafers

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A shirtdress in a cotton or linen blend is ideal for the “soft loafer” and boat shoe trend that’s everywhere this fall. The duo conveys freshness and elegance without much effort. Add another trendy item—the trench coat—on top if you need another layer.

The Tobie Shirtdress by Exquise

Quince Italian Leather Soft Loafers

Short dress and flat boots

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For the cooler days of September, a pair of tall flat boots with a short dress give a youthful and edgy look. Add eye-catching layers—tights, socks, even an oversized button-down shirt—underneath for warmth and additional flair.

Missactiver Pleated Button-Down Shirtdress

Reformation Dominique Knee Boots

Flat shoes with a skirtSkirt trends come and go every season, but one thing that never changes? Flat shoes always go great with garment, no matter what hemline is popular at the time. Here’s what is in fashion this fall.

Pencil skirt and chunky loafers

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This contrast between classic and modern is perfect for those who want an updated work look. Chunky loafers add a bit more personality and flair to the sobriety of a pencil skirt.

COS Sheer Column Skirt

Quince Italian Leather Lug Sole Loafers

Pleated skirt and ballet flats

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A pleated midiskirt, when paired with elegantly cut ballet flats, adds vibrancy and lightness to a look. It’s a timeless style that works for work meetings, dinners with friends, or a romantic night out with your partner.

Tory Burch Plaid Golf Skirt

Vionic Alameda Flats

Minimalist miniskirt and sneakers

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If you are looking for a youthful and relaxed air, pairing minimalist basics—like a sweatshirt and simple miniskirt—with trendy sneakers brings the right balance of freshness and elegance.

Reformation Pleated Skirt

Adidas Taekwondo Sneakers

Flat shoes with jeansJeans are a bit of a wildcard piece this fall, thanks to all the new cuts and washes that are currently in fashion. So let’s break down how the fashion pros are styling their flats and jeans.

Straight jeans and loafers

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A pair of straight jeans with flat loafers is the perfect formula for an effortlessly chic look. Do a blouse or a light sweater if you’re heading to the office, or a casual knit and jacket on the weekends.

Levi’s Wedgie Straight Jeans

Reformation Ruched Penny Loafers

Flared jeans and ankle boots

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This trendy cut looks best with flat ankle boots if you want to elongate the figure and get that updated ’70s look. And who wouldn’t want that?

Lee Legendary Flare Jeans

Madewell Lexie Ankle Boots

Cuffed jeans and ballet flats

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Cuffed jeans allow you to show off your ballet flats in all their splendor as well as bring a quirkiness to an otherwise casual look. Add romantic details like a ruffled blouse, pleated bag, or statement necklace.

We the Free Isabelle Slim Cuffed Jeans

Doeyg Mesh Ballet Flats

A version of this story was previously published in Glamour Mexico and Latin America.