Elevated Casual Outfits for the Weekend

Has the weather cooled yet where you live? While it’s still pretty warm in the afternoons here in Chicago, it’s freezing in the mornings and evenings. And when I get up in the morning, all I want to reach for is something comfy and cozy. Give me leggings and an oversized sweater any day, especially on the weekends when I don’t have to dress up for work. But, instead, why not try another option? There are numerous ways you can look stylish while staying comfy, too. So, I created five elevated casual outfits to inspire your weekend wardrobe. You can easily recreate these with items you probably already have in your closet. Let’s get started! Oh, and don’t mind my little photobomber.

Elevated Weekend Style

1. Turtleneck, Slouchy Wide-Leg Jeans, + Chelsea Boots

A turtleneck is a classic fall staple, but pair it with slouchy wide-leg jeans, and you’ve got yourself an effortlessly cool outfit. Opt for a fitted turtleneck – I choose a neutral shade – to balance out the relaxed vibe of the jeans. The wide-leg silhouette keeps things casual, but the structured turtleneck adds that elevated touch.

Throw on some Chelsea boots to complete the look. Bonus: it’s cozy enough for those chillier fall mornings without feeling too heavy.

2. Black Tee & Jeans, Plaid Blazer, + Black Ballet Flats

Nothing says polished like a monochrome look. Start with a basic black tee and black jeans for the foundation—super simple but it always works. Then, add a plaid blazer. The structured jacket instantly pulls the outfit together and adds a pop of pattern.

To keep it comfortable and chic, finish with black ballet flats. They’re the perfect blend of casual and refined, giving you that “I didn’t try too hard, but I still look great” vibe.

3. Cropped Cardigan, Denim midi Skirt + Cowboy Boots

Regardless of whether you like country or not, cowboy boots are on trend and a fun way to add a little country charm to your elevated casual outfits. I purchased these ten years ago and rarely wore them, but I am glad I kept them.

I picked a cozy knit cropped cardigan in a fall color and paired it with a denim midi skirt. The outfit feels relaxed but still put together.

4. Hoodie, Trousers, and Adidas Stripe Sneakers

Who says hoodies can’t be chic? Pair a hoodie with tailored trousers; you’ve got the perfect mix of sporty and sophisticated. Choose neutral trousers, like gray, beige, or black, and balance them with a hoodie in a complementary shade.

I finished the look with classic Adidas sneakers and a baseball cap. The pop of blue adds interest to the outfit, and the mix of textures keeps it fresh. This look is ideal for a laid-back weekend afternoon.

5. Button-up Shirt, Jeans, Belt + Mary Jane Flats

The last outfit idea blends timeless pieces with a modern twist. A crisp button-down shirt tucked into straight-leg jeans is the definition of effortless style. The button-down gives a clean, polished vibe, while the straight jeans keep it casual and comfortable.

Add a belt to pull the look together and give your waist some definition. Finish with Mary Jane flats for a cute, feminine touch.

That’s a wrap! Which elevated casual weekend outfit are you going to recreate? Let me know in the comments!

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Also see: Three Ways to Style a Denim Skirt and Casual Weekend Outfit

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Welcome to Thursday Fashion Files! Kellyann and I are excited to have you here. We’d love it if you linked up one of your latest outfits with us at the bottom of this post. Don’t forget to check out our Thursday Fashion Files Pinterest board. Email me at hello@dousedinpink.com if you’d like to contribute to the board!