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Look Book

DATE NIGHT IN THE FALL

sky haarsma

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@theitgirlguideofficial

Fall is in the air, and we all know what that means—it’s time for cozy date nights and effortless outfits that still turn heads. Whether it’s a casual dinner in the village, a solo coffee date, or just stepping out for a spontaneous evening stroll, this look is a total vibe.

First things first—denim. Dark jeans are a fall essential, and they’ll take you from daytime chic to evening elegance in no time. I’m living for Frame’s Le Sleek pair of jeans right now. They fit like a dream and are just so flattering. These jeans are everything because they’re versatile—perfect for a fancy dinner or just grabbing your favorite latte. You can dress them up or down, and either way, you’ll look like you just stepped out of a street style photo shoot.

Now, let’s talk about boots. You know I’m all about a good pair of boots, and this season, it’s all about the sleek and understated styles. Whether you’re feeling a classic heeled boot or something more laid-back like a chunky combat style, the boots make the look. For this outfit, I’m leaning towards something classic yet modern—a boot that’ll last for years and never go out of style. But let’s be honest, the real magic happens when you pair it with a cozy cardigan that feels as luxurious as it looks.

Cue the cashmere moment. This button-up cashmere cardigan is the fall staple. And I’m not just saying that because it’s Mongolian cashmere (although that alone is a selling point). It’s the perfect shade of brown—a warm, earthy tone that literally goes with everything. The way it hugs the wrists with those cute little buttons? Obsessed. It’s the little details like that which make this cardigan a total standout. And did I mention it’s under $90? Run, don’t walk to snag this gem.

Of course, we all know the layering game is key, so naturally, a white baby tee peeking through the sweater’s collar is a must. It adds that subtle contrast that pulls the whole look together. My go-to is always from Eterne—they just get the basics. Plus, their pajama pants? Let’s just say you’ll want to live in them (but that’s a story for another day).

Now, onto accessories—because what’s an it girl look without the perfect finishing touches? When it comes to bags, the options are endless. You could go for something timeless like the Chanel Flap for that chic, forever-in-style moment, or maybe channel a bit of Jackie O with the Gucci Jackie bag. But, if you’re in the mood to turn heads (and who isn’t?), a trendy option like Bottega’s Sardine bag is the way to go. I love how the gold handle ties everything together with the subtle gold accents in your jewelry—hoops, bangles, you name it. It’s those effortless details that take the look from cute to next level.

And who is this girl wearing this effortlessly cool outfit? She’s the girl who can make even the simplest things feel extraordinary. She’s thoughtful yet spontaneous, the type of girl who doesn’t wait around for plans—she makes them. She’s always a little ahead of the curve but never tries too hard. When she walks into the room, people notice her, but it’s her energy that keeps them looking.

She’s the girl who can wear vintage flea market finds as confidently as she wears designer labels. She loves her books well-worn, her mornings filled with the smell of coffee, and her afternoons spent exploring new parts of the city. She always keeps a journal in her bag, right next to her favorite red lipstick (just in case). Her style? It’s personal. She knows what she likes, and she doesn’t need the latest trends to tell her what’s cool. She loves a classic look with a twist, like a well-fitted pair of dark jeans and cashmere layered just right.

When she gets dressed, it looks effortless because it is. She doesn’t fuss over the details but somehow gets them all right. And when you catch her walking down the street, you know she’s a girl with stories to tell—just not all at once.

So tell me, what’s your dream bag for this look? Would you go classic, trendy, or a bit of both? Let’s hear it in the comments!

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  • Being an it-girl isn’t about being a nepo baby or buying the shoes everyone else is buying, and I wanted to create TIGG - my digital magazine - to help show that. Here on TIGG, you can feel like an it-girl not only through reading about new outfit ideas and supermodels, but also through vintage designer finds, wellness, and lots of good food and drinks.

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