When Sal from AlreadyPretty posted that “Color isn’t Cool”, it got me thinking. Sal explores the notion that “black is eternally cool and that neutrals are perpetually chic”, while reflecting on her own style which is bold and colourful. Are neutral outfits by definition more cool than colourful outfits? Can a colourful outfit be cool? And what does “cool” really mean?

You know a cool outfit when you see it, but “cool” is one of those things that is very hard to articulate. And cool is in the eye of the beholder — what makes you look and feel cool might not be perceived as cool by someone else. Since I read Sally’s post I’ve been trying to distill my own vague notions of coolness into something more tangible. I thought about how my clients view the concept, how I try to help them to achieve it in their style, and what it means for me personally. What are the prerequisites for a cool outfit?

It came down to three adjectives: effortless, distinctive and stylish.

Cool Outfits Seem Effortless

For an outfit to be cool, the wearer has to own it. You can’t be “trying”. It must be, and seem, effortless. This is the most important of my three adjectives and it’s all about the style of the wearer authentically reflecting who he or she is through the way that they dress. A gal dressed in an edgy way is cool only when she’s in sync with her look. It’s not only the edgy ensemble that makes her cool, but the fact that she is confident about it and her style genuinely reflects who she is. A fashionable modern classic gal who is in sync with her style looks just as cool to me. The same goes for someone with a bohemian, arty, retro, theatrical or romantic style.

Confidence is crucial. Sometimes a client with a very conservative style explicitly tells me that they want to be more cool, and the way I approach this is in stages. We take the biggest step towards cool that they are comfortable taking. The change makes them feel a little daring, but without making them feel self conscious and doubtful. Once they have mastered this new style, it is time to take another “cool” step.

Cool Outfits Are Distinctive

Just being effortless is not enough. A cool outfit must also be one that sets the wearer apart. This is one of the things that makes cool so hard to achieve, because being distinctive is risky and takes people outside their comfort zone, and therefore outside their “effortless zone”. As I mentioned above, the trick is not to go too far in one go.

An unexpected, but flattering outfit element takes an ensemble from nice to cool. An unpredictable twist, like mixing dressy fabrications with casual shoes, or wearing a classic dress with a punk hairstyle kicks up the cool quotient. For some it’s about making their body art part of their ensemble. For others it can mean wearing a cutting edge bright fuchsia jumpsuit under a strict grey jacket. Instead of wearing a bangle on one arm, wear bangles on both arms. Loosen up an outfit by scrunching up the sleeves. Or deliberately button up a playful blouse to appear more strict. Wear stuff back to front. Match your specs with your scarves. Instead of wearing one brooch, wear three. Wear a very monochrome palette.

All of these examples are about making the outfit noteworthy. In some cases the entire outfit is striking, and in others there is only a single element that sets it apart. There are both large and small ways to be distinctive with your style.

Cool Outfits Look Stylish

A cool outfit is also an attractive outfit, and therefore style plays a part. Wearing baggy sweats and rubber flip flops may be an effortless outfit choice AND will probably be distinctive, but it’s not cool because it’s not stylish.

Fashion isn’t everything, but it is one important component of style. For most people this means that a cool outfit must incorporate elements of what’s currently fashionable or cutting edge, no matter how vintage, retro, romantic, classic or bohemian your style. Note that we’re talking about incorporating an element of current fashion. It may be that your haircut and make-up alone do the trick. Or your shoes and handbag are modern when the rest of you is in thrifted vintage clothing. But without any element of current fashion, you run the risk of looking like you’re wearing a costume, or heaven forbid, dowdy.

This isn’t true for everyone. Some people will pull off being cool in ways that defy the current trends (Gwen Stefani comes to mind), but these people are in the minority. They are defining new trends.

Having Fun, Feeling Cool

An important thing to realize is that we’re all on the cool continuum. Even my edgy, confident clients that turn heads wherever they go are looking to take the next cool step. But their steps are more bold and daring than my clients who are just starting out. What makes it all the more fun is that we never completely arrive at “cool”. There is always an opportunity to stretch ourselves a little and add something new and distinctive to our look. This newness makes us feel more cool. And feeling cool, in turn, gives us the confidence that makes it effortless.

Finally, cool is not the be all and end all of style. You can be stylish and have fun with fashion in so many other ways. In other words, an outfit needs to be stylish to look cool, but you don’t need to be cool to look stylish. Wearing a more expected and predictable, but flattering outfit combination is still 100% stylish in my book.