I need a hat that doesn’t make me look like Benny from Crossroads!

[Peridot1]

I know most of you will be too young to remember him. Suffice to say - not a good look.

I’m mid fifties. Overweight. Fat face and a slightly bigger than average head as some hats seem a bit small.

I wore a fleece hat from Mountain Warehouse yesterday in an ‘I’m exercising so I don’t care how I look’ moment. Then I saw myself in the mirror when I came back. Ugh. I do care. But I don’t want to be cold either.

Afraid I can't help much but had to report that whenever ds wears a particular beanie with his curly hair sticking out round the edges I say "Ooh, Miss Diane!" and every time he looks at me blankly 😂 I think perhaps steer away from the ribbed, cuffed beanies. I have a plain one that isn't too Benny.

It’s hard to look good in a hat. I just do not have a face for hats. Especially beanie type hats.

@MrsEricBana - you need to show him a photo.

Maybe an oversized beanie like this one would be less Benny, and make the face look smaller?

Now we're in Smurf territory.

I wondered about those. A friend has one and it looks good on her. But hats suit her anyway.

@Peridot1, unless you are lucky enough to have a face for hats, I think the most flattering is a huff. like these They are surprisingly warm and a bit glam, as well as machine washable.

Thanks @XingMing. They look interesting but I really can’t see them suiting me at all!

@hollyhope

Now we're in Smurf territory.

I quite liked that one until you mentioned the Smurfs!

I don't suit hats usually but got a slouchy beanie and it looks pretty good. It has a stripe about a third of the way up and somehow this makes it look better than plain ones I've tried

Village hats has a good selection, you might find some inspiration here

How about a big russian style fur thing? Or a beret?

Peridot - I found this guide really helpful, I ended up e-mailing them a picture and they were terrific - www.karenhenriksen.co.uk/style-guides

@MrsEricBana - that made me laugh! Please please watch Acorn Antiques with your ds!

I don't suit hats but I find the best are slightly quirky hand knitted or crocheted slouchy ones in multi colours. Maybe try a craft site like MadeMe, Folksy etc or pay a crafty friend.

If you like them, I think pom pom hats are more flattering than plain beanies; the pom pom adds height.

Hat to exercise in or hat to look chic in? Never the Twain shall meet.

Ha ha! I know exactly what you mean. When wearing a woolly pull on hat I look like a cross between Benny from Crossroads and Cartman from Southpark. Doesn't help that I am overweight!

What I want is a cap - like a baker boy cap but stretchy as my head is too big!

Thanks for all the suggestions. Will have a look.

@Iamthewombat - it’s too go for walks mainly. It’s so cold at the moment I really need a hat. Wouldn’t normally bother.

I looked at some online advice and fedora styles were recommended so I ordered this. It arrived yesterday and looks ok. Better than what I had anyway!

I love Fedoras but they make me look like Freddy Krueger.

A friend of mine wears a baker boy hat which looks good.

I quite like the fedora style one I got. DS(19) did not. We went for a walk and I wore my original one which is turquoise fleece beanie style. He says I have dreadful taste in hats!

I quite like the idea of a baker boy style too.

I will find a nice hat. I will!