My Ultimate Fashion Psychology Guide: How to Look Cool?

How to Look Cool (Fashion Psychology Basics)

• Wear fewer colors, not more

• Repeat outfits confidently

• Choose structure over trends

• Prioritize fit above labels

• Look comfortable – confidence reads instantly

The Magic Formula: Boldness + Restraint

Here’s what I’ve figured out: coolness in fashion comes from the interplay between boldness and restraint. Not one or the other – the conversation between them.

Let’s Talk About Boldness First

Sometimes I look at an outfit and what makes it look cool is something bold. One exaggerated piece – a huge chunky scarf, a statement coat, a sculptural bag, heels worn with an otherwise casual outfit. That one bold choice makes everything else seem cooler by association.

Here’s a practical example: You’re wearing a t-shirt, skinny jeans, and sneakers. Basic tote because you need it for practical reasons. You’re about to leave and you’re feeling… blah. Not as cool as you’d like. You don’t have to change everything. Just switch the skinny jeans for dramatic wide-leg trousers you usually save for fancier occasions. Boom. One bold swap, whole outfit transformed.

The simplest way to use this: when getting dressed, ask yourself – is there one bold item I can build this outfit around? Or if it’s already not working, can I just add one very bold thing?

Now Let’s Talk About Restraint

Here’s where it gets interesting. Often, what makes an outfit look cool is actually the deployment of restraint.

Monochromatic outfits? Restraint. Wearing all black – which is somewhat universally a reliably cool choice – is the most extreme color palette restraint. Tight tailoring, sleek fitted suits, clean lines? That’s silhouette restraint. And it exudes polish and impact precisely because it’s doing less.

I’ll tell you a story. Recently, I was packing for a trip and trying to choose between a dramatic oversized linen blazer (very fashion, very bold) and a simple cropped windbreaker. I was wearing all black that day. Put on the oversized blazer – very fashion. Put on the windbreaker – and my partner immediately said, “The black one looks cooler.”

Even though the oversized blazer was the “fashion risk,” the windbreaker won because of restraint. Tighter silhouette, all-black palette, less obvious effort. He couldn’t explain why, but his gut reaction was clear.

Remember that old Coco Chanel saying? Before you leave the house, look in the mirror and take one thing off. That’s restraint in action.

Here’s Where It Gets Circular (And Magical)

At this point, boldness and restraint might seem like opposite strategies. One turns the impact volume up, one turns it down. You’d think you just pick one, right?

Actually, I think they talk to each other constantly. And that’s where the real magic happens.

When I want to feel my absolute coolest – like if I’m going somewhere and looking cool is genuinely the priority – my most reliable strategy is: all black, fitted clothes, big chunky black boots, rugged oversized black leather jacket. The color palette is restrained. The formality is restrained (it’s laid-back, doing less). But the boots and jacket are bold. And the overall dramatic impact? Also bold. The restraint and boldness dovetail together.

The opposite works too. If your boldness is in color – you’re wearing something really vibrant or mixing multiple colors – apply restraint by simplifying the silhouette. Keep it laid-back and draped. Hair and makeup effortless. Shoes pleasantly dirty. No bag, no heels. The bold colors pop precisely because everything else is pulled way back.

See what’s happening? These two qualities that seem opposite actually feed each other. Enough restraint becomes dramatic in its own right – so the restraint becomes boldness. And for one bold piece to really do its work, you often need to show restraint everywhere else.

The more you play with this, the more they start to blend into each other. It becomes circular.

So Where Do You Start?

Depending on how you dress now – what comes naturally to you, what’s hard for you – either boldness or restraint on its own might be the mental springboard you need. If you tend toward safe and simple, try adding one bold piece. If you tend toward maximalism, try stripping things back.

But if you really want to lean into it, the most fun is thinking about how boldness and restraint affect each other in a single outfit – and what you can change about one by tinkering with the other.

What makes you feel really cool? I’d genuinely love to know.