I think there is a difference between a cool person and a cool outfit. The two often overlap but not always. I can think of a couple of really cool people that really have no interest in fashion or clothes, and a couple of people who dress in a great unique way who are not interesting or engaging.

However this is about how an outfit looks cool so I am digressing.

I like what Rabbit wrote, and Angie very much.

For me there has to be comfort in your own skin,; fierce heels only look cool if you can stride out in them, short skirts only if you are not hitching them down. A touch of the unexpected adds to the coolness.

Famous people who I think dress in a cool way are
- Sarah Jessica Parker
- Diane Kruger
- Emma Stone.

Thanks for making me think about it!

IMO, if a person feels "cool", they aren't. In other words, when I was younger, I would put an outfit on with the intent to look cool, or the intent to look a certain way, but I almost invariably ended up with a teeny-tiny part of me feeling like I was putting on a costume. It hasn't been until recently that I choose items that just feel right to me, and when I put them on I seem to forget all about the clothes. THAT is the authenticity and the grounded feeling that was previously mentioned.

So maybe I look cool to other people, and maybe I don't. Like it has also been mentioned, cool is in the eye of the beholder, and I doubt, for example, that kids my son's age would EVER think their mum was cool (or at least they probably wouldn't admit it if they did). But that's okay, because the last demographic I am looking to appeal to is the high school set!

I think there are different kinds of cool. A cool cat is a vastly different creature from a she's a cool girl from a high school Cool Girl from James Dean cool. And their attitudes and clothing are vastly different in keeping.

I find cool cat cool the most interesting. Its unreactive quality. It doesn't attract me, but I find it the most interesting.

I think I'm she's cool cool. As in, I don't demonize individuals, and your life will not be reorganised around my make-up touch-up routine. I can get further away than 25 feet from the ladies lounge.

Sartorial hall-marks of the aforementioned creatures of cool:

• cool cat: mirrored sunglasses
• cool girl: breezy clothing, long locks
  
• Cool Girl: card-boarded locks, clothing that makes you walk stiff, big purse o' make-up
• James Dean: bien sur, the leather moto

Interestingly enough, Cool Girl is a teenager with lots of friends and James Dean is a teenager with, like, one...

Good points. Cocolion has got me thinking with the question of does female coolness often have a masculine or androgynous element. Maybe it's because stereotypical feminine qualities are often associated with a certain vulnerability? So Marilyn Monroe - beautiful and bombshell, but maybe too vulnerable/fragile to be cool. Marlene Dietrich - super cool.

Adding to the list of cool icons I've gravitated toward at certain points in time growing up:

Beth Ditto (pretty much wins hands down)

(early) Jim Morrison

Han Solo and Princess Leia (not Luke though)

everybody in the movie Crouching Tiger Hidden Dragon and the Matrix

Susan Sarandon (at all ages)

ETA: I like thinking about rachy's typography. Very different clothing/fashions, but all have a certain emotional invulnerability and independence, except maybe James Dean? Not so much with emotional invulnerability...

Some cool women to me:

Idgie from Fried Green Tomatoes
Kate Hepburn
Amelia Earhart

Strong, fearless, and unique, standing up for something. And appropriating male clothes. Hmmm.....

Ehh, I've never understood why you can't feel cool to be cool. The first rule of Fight Club....

Agreeing with Angie - love your explanation rabbit
I think cool also has a certain unexpectedness - like Anna's pastel outfit.

Interesting! Cool for me is more about attitude and confidence. Cool people often have that "je ne sais quois" quality about them. Visually tho I think it's quite subjective and I'm not sure one can separate the visual from the attitude. I tend to think both are required to really attain cool.

I have a book called "Chasing Cool". It's about looking at "cool" from a business and marketing aspect...taking risks is one of the elements the authors pin point, and I think that can be a major element of what makes outfits cool.

Poor Luke. He wasn't cool, but he was supposed to be. Why wasn't Luke cool?

To me it's never about the clothes. I generally agree with Rabbit plus I think it has a lot to do with how a person moves, stands, their glance. I think a cool person is not uninvolved but is very present to their own lives and not checking to see how they're being received. I can think of lots of women who are cool but not dressed in masculine clothes. How about Simone Signoret, Myrna Loy?

And all the Hitchcock Blondes -- they were staggeringly cool but not a bit masculine. Grace Kelly, Tippi Hedren, Kim Novack... silk headscarves and big sunglasses, anyone?

"A word can be anything I want it to be"

Wow, Rabbit, I'd never have thought to call Jim Morrison "cool"; whenever I heard him croon "try to set the night on fire", in my mind, he was totally HOT. Maybe that is the source of Luke's dilemma--Hans Solo is hot, Leia is cool, and Luke is just lukewarm.

And I never could figure out why James Dean got tagged as "cool"; I suffered through Rebel Without a Cause and thought it was an apt title. Obviously JD's brand of "cool" didn't resonate with me.

I'm sticking with my opinion that coolness resides in the neural synapses of the observer. You can feel cool in an outfit but you can't make others see you, or the outfit, as cool if they are not so inclined.

Everyone here is so well versed and expressive. I operate mostly on gut feel. I know Angie doesn't like to use the word cool (or edgy, am I right?). But sometimes I just think it's the perfect word. To me it's a feeling, an aura, something you can feel. Can't put my finger on it, but when something is cool it's cool (and it's usually not me!). Great thread.

Great thread!

First off, I read Angie's post on coolness (effortlessness, distinctiveness and style) and it is bang-on. Fully agree with all her points.

Cocolion's comment about coolness generally having a masculine quality rang true, too. I've always thought that. There are many women I admire, but relatively few who are cool (at least according to what cool feels like to me). I know a lot more men who fit my personal definition of 'cool'. However, I'd add Ellen Degeneres to the Cocolion's list. But then, she's a gay woman with butch (i.e. masculine) style. I know several seriously cool lesbians in real life, too. And of course, these women have a very good understanding of who they are. Maybe because gay people in general have to come to terms with who they are in a world that does not always accept them -- maybe that's part of why they are often pretty cool? Just a thought.

I'm new and am loving reading everyone's thoughts in this thread!

The Brooklyn neighborhood I live in has for a number of years been practically synonymous with "cool" - but a self-conscious type of cool, to the extent that I think it's come full circle and the coolest of the cool have moved on.

The common thread of coolness here is less what is the outfit? and more how well is the wearer pulling it off? Every season I see people wearing basically the same components, but some, of course, look miles better than others. I hate to admit it, and I wish it were otherwise, but all too often body type plays into how cool a look reads. It's easier to pull off contemporary looks with a tall, lean body type, and many locals with that body type take full advantage of it by wearing maximally trendy outfits. Sometimes it works and often it doesn't, but they have a better chance of pulling it off than many others.

A certain marginally-unwashed nonchalance also contributes to looking cool. Think of the members of any guitar band that plays in trendy bars that claim to be dives but serve $17 cocktails - that slightly dirty hair/not-so-fresh t-shirt look. Everyone here wants to look stylishly undone without tipping into full-on grubby. Overly "done" hair or a "trying too hard" full face of makeup doesn't look cool. This can be frustrating because, again, it's up to genetics - if someone suffers from bad acne, it's not cool to walk around barefaced, but possibly less cool to use enough makeup to cover it up!

Rock and a hard place - that's coolness to me. Even the coolest never really feel like they're quite there. Anyone who's totally confident about themselves is more likely a fabulous eccentric than a "cool kid."

Gaylene makes a good point. Poor Luke wasn't hot OR cool. He was kind of whiny. I may not be perfectly clear on what cool is, but whiny it is NOT. Despite the fantastic success of the movies, I think it was poor casting.

*Fight Club* was a cool movie... But the people in it weren't cool... Now I think people would argue me on the movie's coolness because of the vulgarity and grotesqueness, but I'd argue it had its finger on the pulse of something important or meaningful. Which may say something about what cool is.

That it has one of my signature looks, that it looks effortless...

Interesting discussion!

To me, "cool" and "great sense of humor " are mutually exclusive -- cool is too intense, too obsessed with something(s) to truly let go and laugh, especially at themselves.

Laughing is warm, cool is...sangfroid.

I appreciate cool from a distance, but I'm drawn to the Cool Minus types -- the ones who've done interesting things and have confidence in many areas, but aren't afraid to look/be goofy or admit their vulnerability.

ETA How the above translates into clothing for me is like obscenity -- I know it when I see it. :0

Cool is one of those tricksy concepts.

For me cool is entwined with music so my version of cool has a rock element. I find most musicians cool but not many actors/actresses. I also have a heaping dose of masculine in my concept of cool.

I think cool has elements of uniqueness--usually in both personality and style. I find it very difficult to describe. It's one of those "I know it when I see it" thing.