Dressing up in winter – with the drop in temperature, wet weather and wild winds – might have you losing your sartorial sanity. But if you have an imposing dress code to adhere to – or you just want to look a bit more put-together than usual, we’ve picked the best of this season’s occasion-worthy pieces to take the guesswork out of dressing up (while making sure you don’t catch a cold). We’re talking elegant cuts, elevated outerwear, and heavyweight textiles that can bear the brunt of the seasonal chill.

Dress to impress
Always a hero piece, a great dress can reduce the stress of putting a look together. In seasonably appropriate fashion, Aotearoa-based labels are embracing long-sleeved dresses; there’s Paris Georgia’s Otto dress, a slinky and striking knit number with off-the-shoulder detailing, a strong neckline and daring front cut-outs. For a more structured and heavyweight option, the Bennet dress by Florence & Fortitude is an elegant, form-fitting alternative that can easily transition from boardroom to gala. A loose, free-flowing silhouette is a no-brainer to layer on cooler nights, and Daylight Moon’s Moon Rocks dress is a playful pick, with a flattering bias cut that works for a variety of shapes and sizes. Available in a polka dot and a lilac floral print, the beautifully draped dress can easily accommodate some warmer underlayers, like one of Gil Rodriguez’s bodysuits from Black Box Boutique. With layering in mind, don’t let winter stop you from donning a mini – BW36 174’s gem-encrusted velvet mini Rail dress will take you back to the ’80s with its padded shoulders. Layer over some stockings and you’ll be ready to hit the dance floor.

A “going out” top

A polished, long-sleeved “going out” top is a tried and true wardrobe staple. You want a multitasker here – one that can be dressed up to elevate an evening ensemble, or stand in as the “nice top” (as in, “jeans and a nice top”). Local brand Caitlin Crisp has a pretty and poised selection of long-sleeves – we love the crinkled shirring of the black Loveline top, and the puffed shoulder and glove-like fit of the Bernadette bodice. Look for tops with an interesting point of difference – colour, texture and detailing are just as important as cut when it comes to creating a polished look. Benjamin Alexander’s dove-grey Emmet top ticks all the boxes with its floral embroidery, cut-out front and buttoned high-neck. For something even more statement-making, Mount Maunganui boutique Sisters & Co stocks Spanish brand Paco Rabanne and this emerald green, flounce-sleeved top is a show-stopper.

Maximum impact
Maxiskirts are back on fashion’s radar and there’s no denying the elegant sophistication of ankle-grazing and floor-skimming skirts. A bias cut, slim slip skirt, like Gloria’s Silver Play skirt is a great place to start and will be a timeless piece. Long A-line skirts like Marle’s sand-washed silk Bayley skirt create fun and flounce (and allow for some warm underlayers, too). Maje’s metallic pleated skirt is a red-carpet-worthy piece. Thanks to its wide elasticated waistband, defining the waist with a tucked-in top is easy. For a versatile staple that works just as well in the office as it does at an after-hours do, try a maxiskirt cut from a slightly weightier tailoring fabric – like Ruby’s Firebird tie skirt.

Suit yourself

A great suit shouldn’t be reserved for the partitioned walls of the office. A strong silhouette exudes a quiet confidence (they’re called power suits for a reason) – such as Camilla and Marc’s Nolana jacket, a double-breasted blazer with an exaggerated shoulder line, made from a metallic cotton-blend tweed. Designed to be paired with its matching Tailored pant, it’s a party-ready ensemble that’s modern with retro charm. Zambesi’s Silverstream suiting also hints at the disco glitz of the ’70s with its three- (or four-) piece wool and lurex blend. The Tux jacket is a relaxed take on a wrap blazer and has a side tie and buttonless fastening. For a lesson in layering with maximalist appeal, pair it with the darted Mimic bodice, A-line miniskirt and – because, why not? – the Boss coat.

A stylish overcoat
Winter calls for occasions – and forecasts – where you won’t need (or want) to take off your coat. With that in mind, make yours show-stopping and stylish. Emerging ready-to-wear label Adrion Atelier’s bold Scarf Collar coat is exactly that. Constructed in a vibrant mandarin-hued heavy twill, the coat’s lapels extend to drape on or wrap around the body. At first glance, Pōneke-based Rhyana’s made-to-order Clarissa coat makes for a chic and unassuming overcoat – oversized with a Peter Pan collar and wide tie belt. One step to the side and the 100 per cent wool trench coat reveals a boot-scootin’ fringed yoke, inspired by the designer’s late, line-dancing nana Clarissa. For extra-special occasions, go extra glam with a faux fur number, like Kate Sylvester’s Meret jacket. With its leather-look belt, it could give the rock’n’roll vibe of Almost Famous’s Penny Lane or the old-money glamour of House of Gucci’s Patrizia Reggiani, depending on how you style it.

The finishing touch
Footwear and accessories can make or break an outfit. Shoes must always be comfortable – not to mention both weather and terrain appropriate. For the frosty season, you can’t go wrong with a dressy pair of knee-high boots, such as La Tribe’s stiletto-heeled Sloane boot. The warm mahogany croc-embossed leather would add a nice peek of texture when layered under a maxiskirt. When the terrain calls for flats, a riding boot is a timeless and polished alternative. Opt for refined detailing with a point of difference – like Toteme’s Riding boots, available at Fabric or Khaite’s Derby boot from Muse Boutique. Have fun layering boots on top of a stylish pair of stockings like cable-knit woollen tights, or Baobei’s Lace Me Up tights from Black Box. Hats and gloves can also be a sophisticated finishing touch to your winter occasion-wear. Zambesi’s felt beret is cute with its chic tie fastening.