Dresses are a natural summer staple. From the crinolines of the 18th century through to the geometric shift dresses of the sixties, they promote ease-of-dressing and complete a look with just one garment.

“For me, [the dress] epitomises effortless style,” says Oroton’s creative director Sophie Holt. “It’s easy to throw on a beautiful, simple dress in a lightweight cotton, style it with a great sandal and a statement piece of jewellery, and then you’re done.”

Holt says you can easily transform dresses from a casual day look into an elegant evening look with the addition of a belt or an alluring shoe. That’s why it’s important to seek out those pieces that’ll go the distance in terms of classic looks, sustainable fabrics and quality fabrication. Here, Holt shares her favourite styles for every occasion this season.

The shirt dress
Best thrown on after a day at the beach, the beauty of this basic is it can be dressed up by cinching the waist or pairing with the right shoes and accessories. “I prefer a slightly masculine aesthetic, so I wear mine loose and anchor the look with some chunky Isabel Marant slides,” says Holt. Oroton’s recently launched ready-to-wear collection includes a number of shirt dresses, including the clay shirt dress ($399) with a soft tailored, oversized silhouette and elasticated belt to define the waist. The cotton striped short-sleeved dress ($299) is oversized and features drop-shoulder detailing, a banded collar and patch pockets. It’s finished with natural shell buttons running down the front and can be styled with rolled-up cuffs for a more casual look. Other local labels, including Albus Lumen, Matteau Camilla and Marc and Anna Quan also have their take on the classic style.

The party dress
No matter the dress code, Holt recommends wearing a dress you feel comfortable and confident in. “I typically go for something that has a stand-out feature, like a strong silhouette or a striking block colour,” she says. Oroton’s silk full-sleeve dress ($449) has voluminous sleeves that add softness and texture to the otherwise crisp silhouette. Cinch the waist with the optional sash or wear it without for an effortless, easy-fitting yet elegant look. At Sir the Label romantic ruffles are perfect for the festive season, while minimalists can look to New Zealand label Georgia Alice for a black column dress featuring a dramatic circular cut-out in the back.

The versatile dress
Holt says if you’re heading straight from the office to the work Christmas party, you need pieces that will give you the most versatility. “The Sunray pleat dress ($449) looks cool with a striped shirt dress over the top or on its own with gold-layered jewellery,” she says. “Another great piece is our vintage floral print silk column dress, ($449) which can be worn loose or layered up with a relaxed linen blazer.” You can also style it belted at the waist and worn with a heel.

The long-sleeve dress
For summer, a lightweight fabric is key for anything long-sleeved. “This Lemaire midi shirt dress ($471) does this style really well, both patterned and plain,” Holt says. “I also love full sleeves in a longer lined silhouette, like our long-sleeved striped cotton shirt dress ($399).”

The little (or long) black dress
“For a fresher feel, I prefer to wear colour and pattern in summer,” Holt says. But, “for a black-tie event, a simple black dress is always the best. Stella McCartney does an amazing classic gown ($4,200), which ticks the box for being both chic and versatile.” It doesn't tick the wallet-friendly box, but don't fear – Michael Lo Sordo, Dion Lee, Lee Matthews and Bassike have you covered with LBDs in various silhouettes, lengths and materials.

The holiday dress
Holiday dressing should be lightweight, comfortable and easy to pack into your carry-on. “Most of my holiday wardrobe is made up of dresses: kaftans ($349) for daywear, and Isabel Marant does great silk-printed dresses ($1750) for warm summer evenings.”