Please help me change my 'style'

[PeriConfused]

love the look of dresses and skirts, I would love to wear them all the time, but I just keep going back to my jeans and DMs (winter) /. Birkenstocks (summer).
I'm an athletic size 10, 3 boys, job in an office with a casual dress code.
Most likely to be seen lugging big bags of sports kit in and out of the car boot, standing on a football pitch, walking the dog etc
I want to change how I have dresses since time began- jeans and a T-shirt/hoodie or trackies in the house
Has anyone been able to make this change? I'm 50 and feel the need for a change, I would love some advice!

Could you make your tops a bit dressier? To lead into wearing dresses more or to make your current clothes more of an outfit.
Like wearing non stretchy tops that are a bit more structured so instead of jeans and a t-shirt its the 'jeans and a nice top' look.

Would you like a more casual look with dresses, so you can get more comfortable wearing them?
Like the dress, layers and DMs look which is easy to dress up and down, so with a longer cardigan or a leather jacket or a blazer depending on how dressed up you want to be and how practical it is for the weather.
Adding thick tights in the winter or wearing the birkenstocks in the summer without the layers

Blouses maybe as the 'nice top' to make the jeans look dressier?

@Sandysandwich thank you, I often wear a blouse or shirt to work, but struggle to find ones I love online- a search always leads me to dresses that are much more appealing thank the very flouncy blouses I find online.
Any top tips on where to look?
I have a few maxi skirts which I love, but struggle to get the right tops.

@Sandysandwich if I could look like the 3rd pic ina shirt dress and leather jacket I would be delighted.. but mostly I end up looking like an 80s farmhand

I get shirts and blouses from New Look, there are a lot of vibrant and flouncy ones but also some nice understated ones and they last well.

@Sandysandwich thanks, I'll take a look at New Look.
I still can't get my head around wafting about in a dress (with DMs) as a practical thing for my lifestyle though, I know many do, but I really struggle

@PeriConfused I get that, I only get to wear neat or wafty clothes at work, then I come home and put on my baggy dungarees to take the kids to the park

I think you just have to give it a try. Set yourself a challenge to wear a dress every day. There's no reason you can't wear a dress with DMs for walking the dog or taking the kids to school. Every day can be dress up day!

Would shorter dresses work better than long wafty ones? I wear just above the knee with DMs which is more practical than a midi/maxi as nothing to trip over running up and down stairs.
This sort of thing: www.hush-uk.com/iris-dress-midnight/DRS430-401.html

You could ease yourself in with a denim or cord pinafore dress, thick tights and your standard DM’s with one of your standard tops underneath? Or a black denim skirt, tights, DM’s and a top?

Then when you’ve got the skirt bit down try different tops, different styles of skirt, or different dresses?

@DelphiniumBlue, you could be right, I think short is less wafty and more me. I love a good thick pair of winter tights!

@ZealAndArdour thank you. I do wear my denim skirt lots in the winter with wool jumpers. I just need to work towards a dress which means I don't have to work out what too to wear

@schmalex I'm up for a challenge!

The floaty dress trend has gotta be on its way out now / soon so don’t buy too many!