Rolled up jeans with chelsea boots?

[Northernsoullover]

I quite like this look but I'm scared of getting it wrong. Any suggestions for jeans style? I think I'm too old for the gap I think, is it acceptable not to have it? What type of tops style?
I know I could just play it safe and stick to my skinnies but I'm in such a style rut I'd like to try and be a bit more on trend. I'm late forties.

Hiya, I'm 34 and do the jeans rolled at JUST hitting the tip of my Chelsea boots. So I wear ankle socks, and roll them up just enough that you can slightly see skin but barely. I always wear skinny jeans when doing this. Also, roll them up scruffily if that makes sense and make the rolls quite small.
I have 'mom' jeans which I'd wear rolled up with superga trainers, but only really in the summer, so personally I'd stick to your skinny jeans.

I tend to wear a baggy jumper/sweatshirt with either an overcoat undone or a black leather all saints jacket (got mine in an outlet store so cheaper) for autumn, then an undone burgundy parka in winter. Definitely as well just the plain long sleeved tight fitting tops from sites like ASOS can be worn a lot with a casual style.

As Mumsnet has said a million times, good hair, makeup and nails are key. Going to the hygienist quarterly (£50) always makes me feel more confident too.

Thank you. I'm always worried about missing the mark slightly and looking ridiculous. I'll experiment today.