I'm usually happy about what I've chosen to wear to any particular occasion. I manage this by thinking about the setting, and what people should be wearing for that occasion (be it a wedding, beach BBQ, interview, Indian restaurant); I often think 'What would Mumsnet wear?', and then balancing that against what I know about the people who will be there with me, and how likely (or not!) they are to be dressed appropriately. And then I plump for an outfit somewhere between the two.
This has only let me down on two occasions I can think of. The first was at a wedding 10 years ago. It was in August, but it was the wettest August on record, had been raining and stormy for the whole week and the grounds where the wedding was held were knee deep in mud. I wore a trouser suit, but was the only one - everyone else was in their brightly coloured summer dresses, hats, bare legs and sandals. I hadn't taken sufficient account of the the fact people had bought/planned their 'Summer wedding outfit' months ago, and would persist whatever the weather was. Lesson learned.
The second mistake was last night. NYE party at a new neighbour's house. I was woefully under-dressed in smart jeans/boots and strappy top. There were people in evening dresses with fur stoles! I hadn't taken into account the wealth of the area (which in fairness, I was aware of, so should have realised that jeans/boots wouldn't cut it) nor the age of the guests (which I wasn't aware of - everyone else was at least 10 years older than us (I'm late 30s), so were dressed more in a 'This is the one event a year that I get the excuse to wear a cocktail dress to' kinda way). I felt really uncomfortable and under-dressed the whole night.
So what are your tips on getting it right? And when you are not sure, do you feel it's better to be over-dressed or under-dressed? And is there anything you can do when you arrive somewhere inappropriately dressed, to mitigate?
I tend to be under dressed than overdressed and I think I need to start upping my game.
The problem for me is that i don't often get the opportunity to dress up, so if i buy lots of dressy clothes, they will just sit in my wardrobe.
My strategy (which I'm working on) is to go for a smart casual wardrobe which can be dressed up or down with accessories eg a statement necklace, bracelet, going out bag. You can then add/ remove items if needed.