A little pleated, striped, sleeveless shirt dress can go a long way in ensuring you are office-appropriate in any season. Here it is, moulded into a 1950s-inspired look with a little help from a key seasonal piece, the jumper.
The patent leather ballerinas with their half-inch heels put just the right spring in your step - the look would definitely feel uncomfortable with anything high or chunky.
Still, ballet pumps are not the only option. Any pair of low-heeled cute shoes (such as traditional kitten heels or something modern and metallic) will do nicely.
Alternatively, if you want to tough it up just a bit, some ankle booties will do the job and keep the cold at bay at the same time.
And yes, as you can see, the quilted sleeveless biker with gold detailing is still one of the biggest staples. I wear it all the time, as it's the perfect autumn jacket, while it provides the best under-coat layer in winter.
One more thing. Out in the cold, and in this pale sunlight, everything tends to look so bleached out you may need a dash of bold lipstick to spice things up.