Smart boots you can be comfy in all day A smart coat Whatever you have that will go with those two! I'd go slim fit trousers, silky blouse, cardy/soft blazer under coat for wearing in box, ideally a nice hat and gloves. Handbag with secure inside pocket, especially if you're planning on betting in cash! Binoculars if you have them. Jealous!
Same problem here. We're in the Club enclosure. I'm thinking a jersey wrap dress, flat boots, smart parka jacket/coat, across body bag (to safely store the cash!). Have heard that anything goes. Most friends wearing dresses/boots, skinny jeans/heels but have been warned that you are on your feet all day and likely to be very drunk!
Well ive just tried my outfits on and I'm even more confused. The husband says my jeans option is 'dull and boring' and i'm not liking that my dress is 2 inches longer than my coat option. Its not going well at the moment. Oh and him indoors keeps telling me its going to be a lovely warm day on Friday when 13 degrees in my book is freezing.
I always think the women in strappy heels look a bit daft tbh, unless you aren't planning on leaving the box all day. Best bits of Cheltenham are going down to the winners enclosures (which will be knee deep in newspaper and chip wrappers), walking round hte bookies' ring, standing by the rail and watching the horses belt past, and if you're still allowed to do it <nostalgia moment alert> crossing the course and watching one of the chases from inside the track.
It can also be sunny but one of the coldest places on earth, the wind absolutely belts down the course.
I wouldn't wear tweed unless you normally wear tweed, just nice wintry colours in smart cuts and ideally nothing too floaty.
Sounds like you have a Cheltenham-ready wardrobe already!
You shouldn't get muddy so trouser/boots should be fine without wellies - car park is the only place that might be a bit swampy but I should imagine you'll be parked on hard standing if you get there a decent time anyhow.