Fact: I have a lot of hats. Another fact: I don't wear any of them. On the rare occasion I have worn one I get lovely comments - "Ooh what a wonderful hat!" "Don't you look fabulous!" - but it doesn't stop me feeling like a knob. In my mind there are two types of people - hat people, and not-hat people. One-fifth of our population can get away with wearing any sort of hat they like, but much less than one-fifth of us are wearing hats. Why? Don't ask. Or do, I think it's ridiculous. That we don't wear hats, I mean. See, I'm being a hypocrite.
When I distance myself from the idea of ME actually donning a hat, they make a lot of sense. Hats not only keep your head warm, sun-free, cool, whatever, but they give you a whole nother dimension to your outfit. Shoes, clothes, jewellery, you say? Well I've just thrown in a fourth. And for lovers of fashion, that should seem a miracle equation. So why the phobia over hats?
I don't care that I look like an idiot, drag queen, walking circus in any other garment, but I feel overdone and try-hard when I'm wearing a hat. Strangely, though, if I look at a picture of myself I think I rather suit them. Maybe this is the Fashion God telling me to get over myself and wear one?
I worry that if I start wearing hats I become one of those people who wear hideous clothing because they think it looks good on them. I was in a shop last week and a yellow woman walked in. No I mean yellow. Yellow jacket, skirt, boots, earrings, bag, hair clips. The shop assistant smirked and then gushed "Wow! You look amazing!" The look of joy in the yellow woman's face filled the whole room. She got it all the time, and she loved it. She was constantly being provoked into wearing more awful outfits thanks to nasty shop assistants. I fear that the "Ooh what a wonderful hat!" comments may be in the same vein. Are hats my one sartorial weakness?
In an effort to get over myself and to convince you chaps that hats are more than OK, I have decided to help you pick your best. When I say one-fifth of the population can wear any hat they want, I mean people with an oval face shape. For the rest of us there are a few simple rules to follow. Follow these rules and maybe we can get the whole population back into wearing hats like in my Grandma's day. Whoopee!
The Heart-Shaped Face:

The heart-shaped face is wider at the top and comes down to a sharp point at the chin. Heart-shaped faces suit small hats worn high on the head. This balances out a sharp chin. An eye-catching trim or a few flowers poked through the side will draw the eye upwards to help with the balancing act. Heart shaped faces should keep away from wide floppy brimmed hats, as they'll only make your chin look sharper and topple your facial balance into oblivion.




Heart shapes' best hats, clockwise from top left: $34.95 from Portmans, $79 Brixton from Good as Gold, Topshop, and Brixton again $99 from Good as Gold.
The Long Face:

Long faces are just that - long. Hats with a deep crown like a bucket hat are good for long faces, and any other styles that sit low on the forehead - as this helps to shorten the face. Fedoras, bowlers or any styles that you can wear low are perfect for you. Keep well away from hats with ultra-tall crowns - you don't need the extra length in your face.




Best hats for a long face, clockwise from top left: Portmans $34.95, A bucket hat by Brixton $79 from Good as Gold, another Brixton $109, and another straw this time $99.
Hats for oval face shapes:

The oval. Perfectly balanced, elegant, screw you oval. You can wear any kind of hat. At all.

You know the first three (Portmans and Brixton), the grey fedora is by Hills Hats (pop on to their website for stockists), the blue floppy is David Lawrence for $79, and there's that Topshop one again.
Hats for a Round face:

Ol' Kirsten has a round face, and she wears it well. Round faces need hats that sharpen the face and help it to have angles. Medium to large brims are best (a little pork pie perked on the tippy top of you head will make you look like a pork pie), and look for hats with tall or angular crowns. Try to wear your hats of to the side slightly (though not in a gangster way), as this will help to create more angles. Fedoras or trilbies are good for you.



Hats for round faces, clockwise from top left: Portmans, Hills Hats and another Hills Hats hat.
Hats for a square face:

If you have a square face then you have quite a square jaw, and your forehead will generally go straight(ish) along the top. Bowler hats and berets with asymmetrical brims worn off to one side will help to carve off some of the sharp angles in your face. Those elegant floppy JLo hats are also fab for square faces.



The angular ones for a square face - wear them at a "jaunty" (always wanted to use that word) angle. Portmans, a beret from Asos for $49, and a bowler from Topshop.


Now for the JLo styles, David Lawrence $79, Portmans $39, glitzy sunglasses and white flares optional.
Have you got over your hat fears yet? They all look so lovely! Can you help me get over mine? Recommendations and tips would be greatly appreciated.
XX B!
Sponsored links
I've been told I suit hats, and I even quite like them. But the only time I wear hats is for running or costume parties! In my facebook pic im wearing a gangster hat (was a costume party).
Thank you for a wonderful resource just prior to doing a hat making workshop in object design. What I would however be interested in is seeing a follow up article that deals with the subject on men's hats.
Just relocate your office to the middle of a vinyard, then you'd look out of place if you didn't wear a hat.
At #1 - Totally agree. If you are uncomfortable about wearing a hat you just can't pull it off. I have a number of hats and often wear them. They are wonderful when you are having a bad hair day. I just wish there were more reasonably priced hats in different styles and colours. I'm now considering making my own as that way I can really match the colours of my clothes. I do however see myself as unique as very few people I see wear them. I do get alot of comments though - interestingly from guys who will say "cool hat" when wearing my fedora.
I love hats, but never buy them - I have long hair & work in an office - meaning hat hair for most of the day if I wear them through the week. On weekends my issue is again my hair - If I tie my hair up (essential) hat's don't sit on my head right. As I'm not cutting my hair any time soon, no hats for me :(
I like hats. I need to wear them because I have one pupil larger than the other all the time. It's a medical thing. My latest hat purchase it a 1920's clouch at from Aurora Designs. It keeps my head warm and my eyes in enough shadow, and stays on my head in the high Wairarapa winds. It's inspired me to make a 1920's jacket, just so I can match. I have other hats. We need more people wearing hats. I think they finish a style.
@ #6 D, you could tie your hair up under your hat (flat bun); can look either elegant or edgy. Or you could tie your hair on one side (off-centre french braid or platt) and wear a side perched hat/beret, low ponytail, hair out. The only thing you can't do is an eye height ponytail. I love hats! But everytime I wear one out, I lose it. Some bugger thinks it looks cool, takes it off my head (which I actually think is the pinnicle of rudeness, I don't take your top, don't touch the hat!) puts it on theirs, wanders off and I never see it again.
I love hats for the fleeting timespan after I've had my fringe trimmed and the hat doesn't squash it over my eyes but that is a very small margin to work with.
I would also add: I think the reason hats feel like such a commitment is because most other clothing items can more or less be rationalised as functional whereas a hat pretty much says "I am wearing this because it is fashionable and I dare you to disagree".
Ball-goers keep up with Kardashians
Is this the best board on Pinterest?
Hairy-leg stockings cause a storm
Stuff's daily street style: June 2013
The guide to staying stylish over 50
Madness at London Men's Fashion Week
Best & worst dressed: Amfar NY gala
Ten brilliant bags to brighten up winter

Newest First
Oldest First
I wear a lot of hats and even more that I don't wear. I have a theory about hats, that to wear one well you just have to commit to the look. You have to think as you put it on "I will look good" and amazingly you do. If you feel less than average, no hat can save you.