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If I describe this first date, help me plan an outfit!
I wouldn't wear heels, especially if you usually do at work. The way you describe the bar makes me think you don't want to look like you're trying too hard. I'd go for trainers and jeans or cigarette leg trousers - or a skirt. Cool but understated.
This is the kind of place I go, and I would agree with the above suggestions - I was bemused by the thread where people said they would never go out in trainers a few weeks back. If it was me I might wear wide leg cropped trousers with trainers, but I am a big fan of midi skirt or dress with trainers too. Have a good time!
I actually have a pair of wide black trousers that are full length and midi navy ones that I do wear with Supergas and Gazelles. With the black ones, I'd wear my cropped black leather jacket. But I never know what to wear over the mid length navy ones.
What would you usually wear over your wide leg trousers? It's still a bit too cold for nothing I think!
Mine are black, so I have worn them with a black biker jacket and a dark blue denim jacket - on top variously a striped long sleeved top, a black Bella Freud jumper, and an orange sweatshirt. I've actually worn nude fishnets underneath on colder days, then black Stan Smiths or gold Nikes.