How would you wear shorts for winter?

[ladyandthechocolate]

I quite like the idea of some shorts for winter with thick tights. How would you wear them? I have some slightly distressed biker ankle boots which I thought could work. What about top half?
Suggestions appreciated!

With thick tights and over the knee flat suede boots.

Either a thick roll neck sweater or a floaty blouse with perhaps a cardigan.

brrrr

I think you have to be careful with knee high boots (or over knee) and shorts or you can start to look a bit principal boy. IMO, biker ankle boots a much better bet, especially if your shorts are short shorts.
I have some short grey tweed shorts which I wear with short biker boots or these or these for evening. Daytime I wear with chunky poloneck or cardigan (I think shorter length cardigans look better than longer boyfriend length if your shorts would be shorter than the cardigan iyswim.
Evening I wear with fine wool or silk jersey tops (Kew/Toast) with a statement blingy necklace.

I have just ordered these longer cullotte style shorts which I think might look ok with a knee high flat boot, otherwise will wear with same options as before.

Thanks. I have purple aged suede over the knee boots and biker boots so I will try both. Need to find some shorts now.

It's the principal boy look that drives men mad with desire

Really Bonsoir? Just makes my joker of a husband shout "It's behind yooooooou!!"