Picking outfits for festive season?!

[CraftySwan]

The past Christmas season made me quite stressed out about how to plan and pick the best things to wear across all the events - work party, drinks with friends, hosting and the big day. I just ended up going with something basic for all of them but I didn't feel particularly good for any of what I wore. Would love to be a bit more stylish this year.

Any advice or insight into how you'd approach planning outfits that make you feel good and stylish across all the big holiday events? Trying to avoid a repeat this year!!

I think about the sort of events I go to, and what works for me, and then plug any holes.
So for me, I rarely go to extremely dressy events, mostly I want something to wear to things like house parties, pub, bar, occasionally a venue for someone's big birthday, maybe meals out or theatre but never black tie.
I've got a lovely velvet printed shirt ( Anthropologie) and a couple of bright coloured oversized silk shirts that work for most things. I've just bought a longish black glittery top. I'll wear these with jeans or black trousers. This type of outfit has worked for me for the last 30 years, with variations on the style of jeans/trousers/skirts.. it used to be very short black or denim skirts rather than jeans!
I have a couple of dresses that are quite funky,in red and cerise. Both button up the front so can be worn as a jacket if the mood takes me, or as a dress with tights/bare legs. I have a black leather jacket and denim jackets, and a long red coat, and boots of different heights and trainers in a variety of colours, and a black wrap dress for funerals or more formal events. Obviously I have a lot more clothes than that, but those are the ones that I wear to go out or host at home. I go for comfort but like to look good too.

We went out for dinner New Years Eve - just a normal meal, not a gala night, and a couple were there who were dressed to the nines. He was in full tuxedo and she was wearing a long sparkly gown. They looked fab, and when I complimented the woman, she told me she had dressed up as there were not many occasions these days for full on glamour. Next year I think I might follow and dress up for everything.

I quitefancy a nice tailored women’s tuxedo, a full on gown, and shorter cocktail dress.

I made a list of what I wished I'd been wearing this Christmas and I've tried to buy it so I've got it in my wardrobe.

So we went for Christmas drinks at friends and I would have liked to wear a velvet trouser suit, so I've bought one. I will be wearing it on Valentines night too.

On Christmas Day I wanted to wear a red satin blouse with red kitten heels, with either a faux leather midi skirt (just purchased from M & S) leather leggings or wide leg leather or wool crop trousers.

NYE I actually wore black sequin trousers, a black satin blouse and black velvet bow sling backs. Lots of jewellery - I'd actually wear that again.

I spent quite a bit (for me) on a dress I love and wore it to several events. I quite like wearing the same dress as it starts to feel like a uniform.

I also have a bright coloured pleated skirt from Zara. Didn't wear it this year but it can be dressed up or down and I will get more wear out of it.