Why don’t I suit skirts/dresses?

[SomewhereNow]

I love the current look of longish skirts or dresses with trainers but honestly I just look ridiculous when I try to dress like that. I’m short, booby and not especially thin which doesn’t help but I’ve seen people with similar figures who can pull it off - I just look really frumpy. Am I destined to live in jeans and hoodies because I can’t seem to do anything more girly 🙄

I don’t think the dress and trainers thing is for everyone. I wear lots of different styles of clothing and am a lot braver style wise than a lot of people but it doesn’t work for me either. Yes to trainers, yes to skirts and dresses but not together. I actually think that while lots of people can pull it off and look really cool and effortless, it can also look quite contrived

Meant to add why don’t you try dresses with boots or sandals season dependant instead of trainers, it’s a far easier way to wear skirts

You sound like me op I have a long body & short legs (although I’m average height) so midi dresses & trainers make me look dumpy
Definitely think dresses & boots are the way to go although I think your boots need a bit of a heel

What sort of boots would work? It feels too early for boots now which is why the trainers would be perfect if I didn’t look such a lump 🙄

If you are determined to go with the trainers version, perhaps try a daintier version and see if that looks better on you. Even more of a Converse style. Not necessarily branded and if it suits you,you can dye a couple of white pairs in different colours to match your wardrobe. So you still retain the comfort with a nod to the trend.
Or try ballerina style shoes or loafer styles until the weather allows for boots.
With your body shape as you describe it, you probably have to be a bit mindful of where your waist line sits, so it might be helpful to adjust this with a belt so that your bust line and waist are defined.
There was a recent video on Trinny London YouTube channel with a wonderful lady who had a style session to figure out a more dressy take on clothes. She wasn’t tall and had a larger bust. She might not look exactly like you shape and size but you might find some useful tips that you can relate to.