I haven't worn a skirt or dress in 22 years...help me!

[MedusaIsHavingABadHairDay]

Seriously. I know it's 22 years because the last time I wore one was actually my wedding day and it's our anniversary next week!

I'm 44, slim (5 ft 6 , 9 stone size 10 pretty much) and I live in jeans at home and at work.

I look at all the people my age looking nice in knee high boots and casual skirts/tunics and would like to be brave and try as I feel so frumpy, but I have no idea where to start..or how to put an outfit together! Pathetic I know :/ I haven't even managed to embrace leggings, it's just jeans and trousers.

Please nice ladies.. help me find some nice (and not to expensive..Fatface/Next is about my limit) skirts/tops combos that would make me look a bit nicer. I would love to go out for my anniversary in a skirt (tho DH might faint with shock!) :)

Ok, would you prefer a dress or skirt? What is your bodyshape and colouring like?

I think a skirt.. (seems less drastic ) I'm of the tall and lanky variety.. skinny legs flat bum (no boobs either!) I have a small waist which at least gives me shape! Quite broad shouldered tho..my bust would fit in an 8 but my shoulders need a 10 or 12. I have light brown shoulder length hair and fair freckly skin. I tend to live in navy and shades of brown and have NO idea what else might suit me! ANy ideas welcomed!!

Can you wear heels?

Oh, hadn't meant ot post quite yet

Where are you planning to go for your anniversary, formal dinner? Pub? Club? Cinema?

I'm a similar shape to you and I find a fuller skirt balances my shoulders well and creates a sort of fake hourglass. TBH a dress might be easier to wear than a skirt.

How about this with this?

No idea what sort of colours you like...

Heels?? Not really as DH is a short arse bless him and I have the coordination of a drunken moose! Flatter is probably safer..

Actually on my anniversary I'm doing a Rockchoir concert so I'm expecting a quick pub trip or indian restaurant afterwards!

I have no idea what colours I like either I really am THAT hopeless:(

What do you think of starting out by wearing a very casual skirt, e.g. a denim one or chino type fabric, they would work even flip flops in warm weather, then go from there? It might not work for your evening out, but might get you more used to the idea, without you feeling too awkward?

I've worn jeans pretty much every day of my life, with work being the exception, where I have my trusty black trousers that I've worn every day there for years, so I can empathise. I do have a fab Calvin Klein casual beige skirt that gets worn only when the weather is too hot for jeans!