Winter Workwear style

Let’s be real — getting dressed for the office in a Sydney winter is a sport. One that involves battling wind tunnels, unpredictable aircon, and footwear that’s stylish and allows for a midday power stomp. Here’s a lil winter workwear style diary from someone who’s just trying to keep warm, look vaguely put together, and make it through the week with semi-washed hair.

The Real Struggles of Corporate Winter workwear style

Before we get into the outfit scroll, let’s unpack the chaos:

1. Office Aircon: Never know if I’m walking into a bottle-shop cool room or a Bali resort.

2. CBD Wind: Harsh, biting, and somehow always targeted at my ankles.

3. Shoes: Must be tall enough that my trousers don’t drag through puddles (ew), but comfy enough to walk ten blocks for a salad.

Case in point: I recently picked up these square-toe slingback pumps from Charles & Keith — stunning, but the strap is more of a suggestion. My power walk has been replaced with a delicate shuffle. Still, they’re cute. We move.

pumps in question

The workwear style Fits

1. Probable Wednesday Fit - Simple. Predictable. Low on laundry. That kind of outfit where the pants does all the heavy lifting.

2. Mystery-Day Green Moment - Unclear what day this was, but I was feeling powerful in green. This top was a $1 op shop find from six years ago — still a fave. Wore it like I was ready to present a billion-dollar finding.

3. Running Late, New Bag - A chaotic morning. Hair: not my day. Mood: frazzled. Outfit: decent thanks to my tote that’s doing most of the work (and emotional support).

4. Mood was up. Must have been a Friday. Definitely treated myself to an extra coffee this day.

5. The non-slick back pony suggests a possible late start, and accidental sleep in... but I appreciated the more girly-forward look and the brown colour combo I managed to compile.

Current: Winter workwear Staples

Some pieces have been on heavy repeat — because when it’s cold and you’re running late, the formula matters.

1. Black Baggy Trousers (Camilla and Marc)

2. Oversized Sweater Vest (op shop find)

3. Slouchy Brown Tote (Amazon)

4. Jewellery in Rotation:

   1. Chunky gold pieces (Oroton)

   2. Silver rings I found at a crystal shop

   3. Kmart hoops I will defend with my life

Jewellery has become my secret hack to improving the 'I tried' aspect. I'm not really a makeup to work girl, so this is my compromise.

Reality Check: No Steam, No Shame

Let’s be honest — several of these outfits feature wrinkled skirts, un-ironed collars, and rogue lint. I’ve been choosing sleep over steaming. No regrets. (Okay, some regrets.)

Tell Me Your Winter workwear Hacks

If you’ve got tricks for staying warm while still looking corporate cute, please drop them in the comments. I’m currently layering thermals like a 70-year-old mountain trekker under my button ups and pretending no one can tell.

with love,

Delaney xx