Chelsea boots- how to????

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So after umming and ahhing on another thread, I bought the Chelsea boots I was pondering over in Sainsbury.
But now I'm just not sure 'how' to wear them. In my head, they'd go well with my dresses and leggings but I'm not sure if they show too much sock. I know it would be better with tights but I hate them and lots of my dresses are a bit short to get away with just tights for work.
I've looked in Pinterest and it suggested rolling them up over jeans, which I've tried with both black skinnies and girlfriend. But what on earth do I wear on my feet! I can get away with trainer type socks in Autumn to have a bare ankle, but what when it's cold? Do I clash colours? A grey marl? Or plain black.
This is all too complicated. I think I should just buy some Acne Pistols instead. Or new biker boots.
(Excuse all the crud on my floor!)

I think both pictures look lovely! Can you not pull your leggings down over your sock? Mine are mostly quite long so I pull them right down.

your jeans are too wide IMO the side shot looks odd. I would waer with not too skin tight skinnies

and I wouldnt wear with dresses

no to pistol/cowboy types this year.. think are old hat verging onto mumboot

whereas ironically the MUMBOOT itself is coming back in ( think black wiht medium chunky heel)
www.topshop.com/en/tsuk/product/shoes-430/boots-460/ankle-boots-3106670/monopoly-pointed-chelsea-boots-4651585?bi=1&ps=20

Brenda, those remind me of the sort of shoe Buffy might wear!

I like both pictures and would def wear those boots with a dress or long tunic tops.

black socks under the leggings will be invisible. They look good in both pics.

I love a Chelsea boot, and wear mine with skinny jeans rolled up to just above them, plus dresses and opaque tights. (I have some black socks which have a kind of lace edge at the top which are good with the jeans.) I think they look good with dresses in general and in your picture.