8 Straight-Up Facts About How to Look Cooler

There are certain girls (like sisters Cipriana Quann and Tk Wonder, pictured below) that always leave me in awe of their innate coolness. It happens with Phoebe Philo, Chloé Sevigny, Solange Knowles, Debbie Harry, Kate Moss and Joan Didion. And a whole lot of French women. How do they do it? Where does it come from? Can it be achieved with clever clothing choices alone, or are some people just born cool while the rest of us are doomed to a life of mediocrity?

How to look cool


Getty Images

The fact is that coolness is ephemeral, hard to define using any other words and definitely comes from a confidence within. But I reckon you can hack your way to a certain point because most of the time, being cool is just about being—and truly accepting—yourself. This month, we're focused on being a little bolder and braver, so above all else, let's remember that being joyful about what you wear is probably the best way to start. Whilst I'd love to offer up a "one size fits all" formula for you to take away and use on those days where you've woken up on the wrong side of cool, here are some suggestions I've mused upon.

1. Being (really) comfortable is cool.

Alexis of Style Memos is a great source for comfortable, chic outfit ideas.

There's nothing naffer, in my humble opinion, than someone struggling in clothes that are too tight or shoes that are too high to stride in. Extreme scruffiness isn't necessarily the answer (although on some that's definitely the epitome of cool), but there is a comfy, relaxed, "happy with myself" middle ground I think is easy to find these days. Why easy now? Well, there's been a steep rise in brands producing that breed of simple throw-on clothes: Think of COS and Weekday on the high street, for starters, or the proliferation of cool sneakers to choose from.

2. It's a cliché, but wearing sunglasses does make you feel cooler.

White sunnies are trending—Maria Alia's are from a brand called Monarch Tokyo.

It's an indisputable fact: Sunglasses (when worn in the sun—please not indoors, at parties, etc.) do make you feel cooler. Whether it's the anonymity they offer or just the fact that the right pair can really frame one's face beautifully, we'll never know. Side note: Have you noticed that glasses chains are making a comeback?

3. Sticking to your personal style is cool.

Nnenna always looks so good in her pretty dresses and simple accessories—never too try hard.

If your vibe is super '70s and '70s trends aren't appearing on the runways, who cares? If that's your style, that's your style, and more power to you for staying true to what you love and what's already in your closet. On the flip side, if you take great pride in being a chameleon and a trend hunter, go forth and conquer.

4. Owning items that tell a story is always cool.

Clothes that have meaning feel like they were destined to shine in 2018—whether it's your newfound interest in sustainable fashion brands or you're making like Solange and crafting an aesthetic related to your artistic outlook and creative place in the world. There's nothing cooler than being able to talk enthusiastically and positively about what you're wearing.

5. It's definitely cool to be kind.

Anna Vitiello (right) and Bettina Looney (left) are two of the friendliest influencers on planet fashion.

Hugs are the hippest accessory in town right now. The industry has been through—and is still experiencing—a major shake-up, and one of the fantastic things to come out of that is our desire to surround ourselves with good people. BrownsFashion.com has basically made "It's Cool to Be Kind" its entire mantra, and we're down with that.

6. Screwing up and starting an outfit again doesn't mean you're not naturally cool.

How to look cool


Getty Images

Ask any style maven and she'll probably tell you the same thing (every interview I've ever carried out with a fashion expert would back this up). It's very normal to have to get changed and start again with some outfits. Cool fashion gurus don't always just fling stuff on—I'm certain that's a myth in need of crushing. Of course, I don't want to make you late for work or have your friends start uninviting you to things, so I'd suggest testing things out the night before.

What a little go-with-everything beauty.

7. Being nonchalant in 2018 is over; it's cooler to smile and communicate.

If anyone gives good smile (and life advice) on Insta, it's Erica.

If you think of the hippest corners of creative culture over the decades, there hasn't been a great deal of grinning captured on camera, but we think that's changing.

Get snap happy, why don't you?

8. Wearing the same things over and over creates a certain coolness.

How to look cool


Rex Features

From the Olsen twins to Carine Roitfeld, there's absolutely nothing wrong with having favourite looks, items, brands or a formula to provide you with a handy uniform to live by.

If you always wear black, head to a discount site like The Outnet to stock up on quality pieces.

See? Looking cool is a total doddle.

This story was originally published at an earlier time and has since been updated.

Related Stories