With each passing season, a new “it girl” look makes its debut. This winter, it’s all about embracing the “rich messy girl” vibe—a look that speaks of luxury and effortlessness all at once. Think cool confidence, a sprinkle of chaos and a wardrobe that whispers sophistication while screaming individuality. Here’s your ultimate guide to achieving this chic, laid-back aesthetic.
The Hair: Controlled Chaos
It all begins with the hair. The “rich messy girl” look demands an effortlessly tousled style—think Serena van der Woodsen from Gossip Girl. Her hair always seemed like she rolled out of bed, brushed it once and walked straight into a designer photoshoot.

The secret? Volume and texture. Use a volumizing mousse or dry shampoo to add lift and make sure not to overdo it with a curling iron—loose waves or slightly unkempt strands are your best friend. Aim for that perfectly imperfect balance that says, “I have better things to do than spend hours on my hair, yet I still look good.”

The Accessories: Hats, Shades, and a Big Purse

No winter look is complete without the right accessories. A Russian-style fur hat or a chic headscarf is a must to elevate your ensemble. The hat not only keeps you warm but also adds a perfect touch that screams old-money. If headscarves are more your speed, tie one loosely under your chin, letting the ends flow freely.

On bright winter days, don’t forget a pair of oversized sunglasses. Choose bold frames that make a statement—they’re as functional as they are iconic. Whether you’re hiding last night’s smudged eyeliner or simply adding an air of mystery, big shades are non-negotiable for the rich, messy girl vibe.

And, of course, don’t leave the house without an oversized bag. A big purse not only adds to the luxurious feel but is also practical—you can throw in everything from your skincare essentials to a pair of backup shoes. Look for structured leather totes or slouchy designer hobo bags in neutral tones to tie your look together seamlessly.
The Makeup: Subtle Drama
The makeup for this look is all about balance. Go for a bold lip—deep reds, plums or even a classic berry tone work beautifully against winter’s muted backdrop.
Pair it with a smudged, smoky eye for a hint of drama, but don’t aim for perfection. This look thrives on a touch of discourse, so let your eyeliner be slightly imperfect or your eyeshadow softly blended for that lived-in feel.

The Star of the Show: Fur

No “rich messy girl” outfit is complete without fur—faux or vintage, of course. A big fur jacket is the ultimate statement piece, tying the entire look together. Choose something oversized and plush, preferably in a neutral tone like cream, beige or charcoal gray, though jewel tones like emerald or deep burgundy can make a bold impact.
The fur coat isn’t just a fashion piece—it’s a lifestyle statement. Draped over your shoulders or tossed on nonchalantly, it exudes an air of luxury that feels both effortless and untouchable.
Bringing It All Together
The beauty of the “rich messy girl” aesthetic lies in its contradictions. It’s polished yet unkempt, bold yet understated, glamorous yet grounded. To truly embody this look, don’t overthink it. Mix textures, play with proportions and let your confidence shine through. The key is to look like you just walked out of a private jet—no matter where you actually are.

This winter, channel your inner Serena van der Woodsen: throw on your fur, grab your oversized bag and strut in a pair of chic booties. Embrace the art of casual luxury. After all, being a little messy never looked so chic.
Tag @VALLEYmag on Instagram or X with pictures of you executing this winter look!
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