Fashion

How to style a sundress from classic to chic for summer

It’s surprisingly easy to make the simple dresses look chic.
how to style a sundress  Streetstyle during Milan Men's Fashion Week on June 23 2025 in Milan Italy.
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Sure, figuring out how to style a sundress can be as simple as just putting one on. But even the most run-of-the-mill floral summer dress can feel surprisingly fresh when it’s paired with trendy accessories. Beach bags, light jackets, classic pearls, chunky, knee-high boots – your choice of accompaniments can take things from romantic to edgy to eclectic.

My advice? Don’t fall for the anti-sundress propaganda. Although it's a staple that comes back in style every year, there are endless ways to wear it in a way that feels elevated, style-forward, and in no way basic. The key when styling a sundress is all in the details. Ahead, six new and improved ideas for how to style a sundress — and make it feel incredibly cool in the process. After something else? Shop summer dresses with sleeves, petite dresses and floaty dresses, adored by our editors.

Featured in this guide:

Me + Em Icon Oversized Blazer
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Mansur Gavriel Mini Filo Bag
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Damson Madder Genevieve Midi Dress in Rose Print
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For work (and happy hour)

MILAN ITALY  SEPTEMBER 18 A guest wears twit gray jacket from Chanel and Luisa Beccaria floral dress during the Milan...
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Introducing an oversized blazer to your sundress outfit adds a bit of sleek, academic flavour. This combo will make any simple frock instantly feel more polished, especially when you style it with a pair of posh contrast-toe pumps.

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Sisterhood Mathilda Dress in Lemon Fleur

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Me + Em Icon Oversized Blazer

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Next Bone Forever Comfort® Slingback Square Toe Block Heels

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DeMellier The Vancouver Clutch


For a music festival

PARIS FRANCE  MARCH 05 A guest wears light brown hair a pale yellow with burgundy and purple floral print pattern satin...
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Dresses usually take a back seat when it comes to festival style. But when styled with a pair of chunky moto boots and a cute, functional crossbody bag, flowy sundresses of any length feel totally relaxed and ready for a day full of dancing around a field.

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OP X Mary Quant Connie Dress

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Steve Madden Benedict Brown Leather Biker Boots

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Sloane Hobo Cross Body Bag

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Wave Earrings


For transitional weather

NEW YORK NEW YORK  SEPTEMBER 13 A guest wears shoulderlength straight brown hair parted in the center narrow rectangular...
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If you’re eager to get a jump on the summer styling experience but the weather simply won’t cooperate, look no further than the beloved lightweight suede jacket. Finish with coordinating footwear — I suggest swapping thigh-high boots for suede mules or sandals — and 1990s-inspired sunglasses to edge up the dress.

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Damson Madder Genevieve Midi Dress in Rose Print

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Reiss Cara Petite Suede Funnel-Neck Bomber Jacket in Neutral

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Sheepskin Wedge Mules

Le Specs Outta Love Oval-Frame Sunglasses


For a family gathering

MILAN ITALY  SEPTEMBER 21 A guest wears earrings a necklace a white cloth bag a colorful floral patterned gathered dress...
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If you’re dressing for a birthday picnic or a family dinner, a whimsical printed sundress is always a solid option. Keep the vibes sweet and sophisticated with a pair of velvet Mary Jane flats, minimalist jewellery, and a summery woven handbag.

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Nobody's Child White Floral Starlight Midi Dress

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AEYDE Uma velvet Mary Jane ballet flats

Solid Gold Floating Diamond Necklace

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Raffia Fish Clutch Bag


For Casual Friday

NEW YORK NEW YORK  SEPTEMBER 15 A guest wears long wavy light brown hair with a center part black round glasses small...
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An easy tote bag and a pair of glove flats give a cool grandma vibe (complimentary!) to the standard sundress. Choose any layer you like to finish off the outfit for your day; if you’re off to the office, a light cardigan offers more coverage and protects against overactive AC. It’s also a great choice for a brunch or a casual date night look.

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Liberty Bridgerton Bouquet Parade Voyage Sun Dress

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Free People Going Places Cardi

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Parfois Leather Ballet Flats With Elastic

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J&M Davidson Escargot Tote


For summer vacation

PARIS FRANCE  SEPTEMBER 30 A guest is seen wearing a green sweater yellow floral dress green and tan bag and white heels...
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In my opinion, no off-duty outfit is complete without a bright jumper wrapped stylishly around your shoulders. It adds a final touch that makes any look feel complete – and the same goes for sundresses. Add colourful earrings, heeled flip flops, and a barrel bag to pack on the whimsy, especially if you’re headed somewhere tropical on vacation.

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Ghost Crepe Floral Midi Tea Dress

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Knitted Jumper

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Ganni x Melissa Thong Kitten Heel in Red

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Boden Mega Jewel Earrings

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Mansur Gavriel Mini Filo Bag

A version of this article originally appeared in Glamour US.