LoveShackFancy's Most Wanted Dresses — The Chessie & Beyond

If you've spent any time in the world of romantic dressing, you already know that a LoveShackFancy piece isn't just a purchase — it's a point of view. The New York-born label, founded by Rebecca Hessel Cohen in 2013, has spent over a decade perfecting the art of whimsy: sun-drenched florals, frothy lace trim, hand-smocked bodices, and silhouettes that feel at once nostalgic and completely of-the-moment. The LoveShackFancy Chessie dress sits squarely at the centre of that philosophy — a style that captures everything the brand does best in a single, effortlessly wearable form.

The Chessie, like many of LoveShackFancy's most-searched styles — the Clarissa, the Judith, the Lennon, the Stella, the Natasha — belongs to a lineage of dresses built around the idea that getting dressed should feel like a small, daily joy. These aren't garments engineered for boardrooms. They are made for golden afternoons, garden parties, and long weekends that need no excuse.

Explore the full LoveShackFancy collection at Lola Dré →

The Silhouettes Worth Knowing

LoveShackFancy works across lengths with equal fluency, and their current edit at Lola Dré spans mini to maxi with conviction. The smocked dress formats — fitted at the bodice, free-flowing below — remain perennial bestsellers, because that particular construction is genuinely flattering across body types. The popover dress silhouette offers a similar ease: pull it on, and the dress does the work.

Discover all Designer Mini Dresses →

Going Long: The Case for a LoveShackFancy Maxi

The brand's maxi dresses are where LoveShackFancy's romanticism reaches full volume. Layers of ruffled chiffon, hand-placed lace trim, and prints inspired by vintage fabric archives make these styles genuinely hard to replicate at any other price point. Think of the Rialto — a cascading floral gown with the kind of movement that makes every entrance worth watching. Or the Story dress in the brand's signature sky mist print, where lace and florals coexist in the most dreamy way. These are destination dresses in every sense of the phrase.

Explore all Designer Maxi Dresses →

Pack your bags: Destination Dresses →

After Dark & Into Occasion

LoveShackFancy has quietly become one of the most reliable names for occasion dressing that doesn't feel stiff or overdone. The Adelaine — a sequin tweed sleeveless mini — proves that the brand can pivot from whimsical to wow without missing a beat. Meanwhile, styles like the Marlia, with its tiered chiffon and lace trim, and the Arletta halter, with its bandana-print richness, move effortlessly between garden soirée and evening event.

Swoon Worthy Dresses — curated for moments that matter →

Meet Me At Midnight: after-dark dressing →

How to Style a LoveShackFancy Dress

The beauty of this brand is that its dresses rarely need much help. A pair of strappy sandals, a demi bag in leather or rattan, and perhaps a light linen overshirt for cooler evenings — that's genuinely all these pieces require. For the mini silhouettes, ankle-strap heeled sandals add polish without overpowering the delicacy of the fabric. For the maxi styles, flat slide sandals or wedge espadrilles keep the look grounded and daytime-appropriate. Those leaning into the Natasha pink palette or the brand's signature rosy tones would do well with warm-toned gold jewellery — thin chains, hoops, a single delicate ring.

At Lola Dré, we've curated the strongest current edit of LoveShackFancy across every length and occasion — from breezy summer minis to ethereal lace gowns. Whether the Chessie first brought you to the brand or you've been collecting these dresses season after season, there is always a new silhouette worth knowing.

The full Designer Dresses edit →

Browse Designer Midi Dresses →

Designer Dresses on Sale — current offers →

Revenge Dressing: dress for yourself, above all else →