autumn fashion -can I ?????

I always say to Tom "don't follow fashion, set a trend! try to be individual", however at his age he has found labels, one of which is Jack Wills. Although I don't do labels & certainly couldn't afford to, as we know it is good to keep an eye on fashion as it generally has an effect on interiors. So having been mooching on line, this season at JW I am drawn to the look and have found some outfits that I love the only question is "can I or can't I?"

Dresses do not suit me and these looks have always been the sort of clothes that I have worn since I can remember, I live in cut off jeans in the summer & have been known to live in them with tights & boots (years ago), so I have a ready supply, I have seen a pair of tweed shorts in M&S, I just need a few fair isle style cardis, I have a rust/orange/tweedy biker style tweedy cropped jacket, so it's just a case of mixing and matching. (I did buy a couple of vintage tweed hacking jackets recently however the one is for a child and the other a fitted size 14)

The only question is am I too old to go short short?

Without the skinny jeans I think that these looks would suit Michael, he has a lovely pair of vintage brogues, and vintage tweed jacket, again I have been looking for ages for a vintage fairisle tank top for him, and it seems that the way to wear a tweed jacket is with a hoody.

So although my inspiration comes from, JW, Joules, Whitestuff(I love their shop fittings),Toast, Cabbages & Roses, etc,etc, I will be re-vamping & re-mixing my existing clothes with a few new items, and a new pair of boots & a pair of brogues, I would wear vintage but it never fits me!!!!

So do I take the plunge?????