If there's one style I'm always chasing, it's the "cool girl" ensemble — that street-style, Pinterest-worthy maven we've all grown accustomed to seeing on our screens. The outfits feel effortless and interesting, somehow appropriate for any occasion without looking stiff, too purposeful, or overly put together. The details don’t always make perfect sense, yet they work together as one cohesive look.
So why does it feel unattainable? Why is it so hard to emulate?
After years of drooling over these women (and honestly, men) who regularly populate my feed, I finally decided to decode the equation. It’s an ongoing investigation as trends shift, fashion evolves, and seasons change — but here are a few ingredients for the "cool girl" style recipe that have helped me get dressed.
Ingredient #1: Buy for the fit you want, not what size you are
This may be the most important — and the least recognized. Women have been conditioned to obsess over size, but I’m here to tell you it’s almost irrelevant. Have you ever copied an outfit you loved and wondered why it didn’t look the same on you?
It often has nothing to do with body size or shape. More than anything, it's about fit.
Don’t hesitate to size up when you want something to drape or hang loosely. And sometimes, you may need to size down for a closer, more tailored look — depending on your body and the style you're aiming for.
Helpful note: In today’s fashion world, retailers have zero consistency with sizing. Every piece differs, even here at Pointed North. Pay attention to sizing notes and recommendations to make the best decision for you.
Ingredient #2: Keep a less-is-more wardrobe, but style creatively
When you break down a coveted “cool girl” outfit, it’s usually surprisingly simple. Most of the time, you’re seeing a well-made white tee thoughtfully paired and layered with standard wardrobe pieces. It’s less about having more clothes and more about how you style them.
One of my favorite trends right now is tying a patterned button-up around the waist. A plain white long-sleeve and jeans instantly become more interesting with that pop of texture and color. Throw on a trench or leather jacket, add a baseball hat, and you’ve got an attainable Pinterest-worthy outfit.
Helpful note: A well-rounded wardrobe comes from mixing retailers and price points. You can find great quality at great prices, but combining high and low gives the best outcome. High-quality loafers can make $20 jeans look elevated. And $100 denim will make that $10 graphic tee look intentionally styled.
Ingredient #3: The "wrong shoe" theory
I can’t take credit for this one — and I can’t even remember where I heard it. But the “wrong shoe” theory encourages you to skip the matchy-matchy pair and opt for something unexpected instead. On paper, a brown leather shoe with a black handbag sounds all wrong, but in reality, it balances out beautifully. It creates an easy, casual feel with even less effort.
Is this appropriate for every outfit? Absolutely not. But for the everyday looks we often struggle with, it works wonders.
Helpful note: This idea applies to all accessories. Hats, scarves, bags, belts, and jewelry can all add interest. Having at least one slightly “wrong” piece keeps the outfit from feeling too polished or stiff.
Turns out, the "cool girl" look isn’t a mystery — it’s a mindset. You don't need to chase perfection, you can trust your eye. Mix, match, adjust the fit, and don’t be afraid to try something a little “wrong.” Use these ingredients as a starting point, then make them your own — that’s where the magic really happens.