This Resortwear Brand Understood The Family Dressing Assignment — & We're Obsessed

Let’s be honest: Sometimes mommy-and-me outfits veer too far into a controlled aesthetic that feels a bit cringe. But when done right, coordinated ensembles can create photo-ready moments that feel plucked from a daydream. So, how do you nail the right mix so you’re firmly in the latter territory? The answer: Kenny Flowers. This global-inspired resortwear brand has mix-and-match looks for the whole family, so you can create winning combinations for every occasion. From Mother’s Day brunch to a family vacation photoshoot, here’s how to ace the family-dressing assignment.

With sun-soaked looks for men, women, and kids, Kenny Flowers offers everything from swimwear and beach coverups to billowy maxi dresses and chic golf wear. Each collection is inspired by a different global destination, from Hawaii and French Polynesia to the Amalfi Coast and the South of France — and many drops include specific Matching Family or Matching Couple looks for effortless mixing and matching. The results are laid-back yet elevated looks that capture the spirt of vacation.

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Ahead, several stunning looks for you, with complementary pieces for the whole family. Whether you have a cabana reserved or just want to channel a carefree aesthetic, there’s something you’ll want to treat yourself to below.

1. This Flowy Tunic Dress In A Bold Floral Print

Inspired by Hawaii, made in Bali, and ready to take you anywhere, this flowy, tiered tunic dress hits all the right notes. The soft, lightweight viscose fabric provides the airiest feel, and the detailed trim and fringe along the V-neckline elevate it beyond beachwear. Wear it as a stunning standalone piece, or pair it with the matching girls’ looks from the Kona collection.

  • Available sizes: XS — XXL

2. A Flamingo-Print Maxi Dress That’s Giving Palm Beach

Perfect for stepping out in Palm Beach (or a Palm Beach state of mind), this breezy maxi dress features an adorable flamingo print, a kicky hem with delicate trim, and adjustable tie straps that not only add visual interest but also provide a custom fit. Wear it for a coordinated sunset date with your partner or pair it with the matching boy’s Hawaiian shirt and/or girls’ resort dress for a darling mommy-and-me look.

  • Available sizes: XS — XXL

3. This Limited Edition Mauna Kea-Inspired Mini Dress

This limited edition print is part of a collaboration between Kenny Flowers and the iconic Mauna Kea resort in Hawaii. With palm trees, surf boards, sandals, beach umbrellas, and tiki torches rendered in an understated color palette, it’s a timeless print that’s incredibly versatile. Dress up this mini dress with some strappy heels and a statement clutch for cocktail hour or dress it down with slides and your beach bag. It pairs perfectly with the men’s Island Time shirt for a relaxed power-couple look, or pair it with the matching items from the kids’ collection for the sweetest family photo shoot.

  • Available sizes: XS — XXL

4. These Positano Bikini Bottoms With 4 Different Top Options

Inspired by the endless summer days of the Amalfi Coast, these chic Positano bikini bottoms can be paired with a range of matching lemon-printed tops for a set that feels as good on as it looks. Choose from a supportive underwire, a sleek bandeau, a classically sporty top, or a spicy string bikini. The citrus-y bright collection also includes swimwear options for your favorite swim partners.

  • Available sizes: XS — XXL

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