Chelsea boots & what to wear with them?

[DancingRoundTheKitchen]

I've just bought some black chelsea boots and I love them but I just don't know what to wear with them.
I imagined them with skinnys / leggings / black tights but when I tried them on I felt a bit silly and like I was trying to look young (I'm 35).
If you wear Chelsea boots with skinnys do you tuck them in or roll them up?
I'm clueless - please help me or I might have to take them back!

Same here. I have seen the most beautiful ankle boots in Massimo Dutti and am unsure how to style them. Straight leg jeans I am thinking as I have size 8 trotters and don't want to look like a right angle.

I have the opposite problem, I'm only a 3. When I tried them with straight legs you could only see a little pointy toe poking out!

I have some Chelsea boots and wear skinnies stretched over the ankle of the boot.

I also like them with mini and midi length skirts. Body con and pencil style look best IMO.

35 is young!

Chelsea boots can be worn by anyone of any age.

When in doubt ask Pinterest.

pinterest.com/search/pins/?q=chelsea%20boots%20jeans

I've just bought some too to wear with skinny jeans and cords and I'm mid 50s.

Don't think they are meant for just children

See now, these look like the boots i wore when I was 19! Can I wear them again?!!

The Chelsea Boot is a classic, I truly think anyone can wear them, from a 5 year old to an 85 year old.

Go get them LauraPashley!

I wear them with skinnies, either rolled up, or over the boot, or tucked in (but I like them with v scrunchy low legwarmers of tucked in, because I am an 80s throwback), or with mini or midi skirts (with opaques and socks!).

I used to know an 85 yr old who wore them a few years back with her smart dark wash denim jeans - she was clearly ahead of the fashion!

Thanks.
Tried them again with black tights and a skirt and skinny jeans over the boots and decided I do love them!
I would wear them with jeans tucked in (and even try some legwarmers) but my ankles are so fat there is no way any extra fabric will fit in there!

Which boots did you get? I'm looking for some tan ones.

You are young!

I would wear them with a skirt (a line), opaques and jumper.

Skinnies tucked in or with dresses and tights. I regularly wear mine with bootcut jeans though as they are the comfiest shoes I own

I got these ones.

Ooh they are gorgeous.

Thanks!
Now I know what to wear with them, I'm well pleased with them.
Is it wrong to be willing Autumn to come quickly. I much prefer buying cold weather clothes?