How to Wear Oversized Striped Sweatshirts: Casual Outfit Ideas for Fall

Cozy Fall Sweatshirts: The Ultimate Wardrobe Staple

While we’ll never turn away our coziest stripes in the perfect moment year-round, we’d like to argue that the *actual* best time to wear a striped sweatshirt is, in fact, autumn. Welcome to the official cozy striped sweatshirt season. We can’t wait for the slow afternoons and breezy coffee runs. So much so, we made a few of our own, and plan to live in them until further notice.

As sweater weather rolls in year after year, we reach for our cozy go-to’s so it’s no surprise that this year, when it comes to fall fashion trends, nothing feels quite as timeless or versatile as an oversized striped sweatshirt. Whether you're channeling that chic, classic French-girl vibe or going for a sporty-cool look, striped sweatshirts are a wardrobe staple that transcend styles and seasons. Luckily, this year, the fall favorite also hits the season’s trend right on the nose. Whatever your lens from bloke-core to coastal boho, these statement pieces have made their way into the collective fashion consciousness from multiple angles.

So striped sweatshirts have come knockin’ once again, and they’re here to offer that perfect balance of cozy comfort and effortless style. For transitional weather fashion, few pieces are better suited to handle the changing temperatures while keeping you looking on point. Not to mention, they’re really fun to style! They truly adapt to all kinds of aesthetics that vibe with your personality and inspirations. That said…we’re here to run through some of our favorite casual fall outfit ideas featuring the striped sweatshirt, and introduce you to Daydreamer’s iconic new collection of sweatshirts that will bring the vision seamlessly to life!

 

 

Styling Tips for Your Cozy Striped Sweatshirt

1. Layering Pieces for Fall: The Transitional Weather Hero

One of the easiest ways to rock an oversized striped sweatshirt for fall is by taking advantage of its loose fit and layering it as an easy throw-on piece. Pair a slouchy sweatshirt over your favorite shorts and a simple tee or tank for a weekend casual vibe in transitional weather. Add sneakers, a baseball cap, and sunnies for a laid-back, sporty look. Accessories like socks—whether you go for ankle or crew lengths—can add that extra pop of personality to the outfit. Try Daydreamer’s half-zip sweatshirts for a modern take on classic stripes. With the intentionally oversized, perfectly slouchy design, these pieces are perfect for transitional weather when you’re not quite ready to say goodbye to summer. For footwear, you could also have some fun and experiment with trendy ballet flats or boat shoes, or go casual with something like Boston Birks and a trucker hat for a less preppy, more relaxed look.

 

2. Statement Sweatshirts and Jeans: The Effortlessly Chic Combo

Looking for a foolproof fall outfit? You don’t always have to reinvent the wheel… Try pairing a striped sweatshirt with straight-leg jeans for an effortlessly chic style. This is one of those fall outfit ideas that never fails. Dress it up with a small heel or a pretty flat to add polish to your look. Or keep it relaxed with flip-flops and a tote bag for a relaxed vibe. Daydreamer’s vintage-inspired fall sweatshirts in classic striped colorways fit seamlessly into this aesthetic. With the thick striped colorways, they offer that perfect medium between cozy fall outfits and coastal vibes— ideal for both city and seaside.

 

3. Mix It Up: Sweatshirts and Trousers for an Elevated Look

If you want to elevate your striped sweatshirt, pair it with sleek trousers for a chic, polished look. This combo blends the classic French aesthetic of the stripe itself with the comfort of an oversized fit. Think Parisian cool meets laid-back Californian. A large leather bag adds an extra touch of sophistication, making this look perfect for transitioning from work to weekend. Daydreamer's vintage-inspired sweatshirts work wonders here, offering a slightly slouchy silhouette that balances out the structured look of trousers.

 

4. The Big Top Meets the Mini Skirt

Nothing says “effortlessly cool” like an oversized striped sweatshirt and mini skirt combo. Whether you’re heading out for a coffee run or a weekend brunch, this outfit brings major fall vibes. You can do this with sneakers or loafers for an athletic-preppy touch, which looks especially cool if you’re styling it with one of our sweatshirts. If you’re looking to take things up a notch, try pairing the look with tall moto boots or riding boots for a cozy, yet edgy fall aesthetic.

 

Find Your Seasonal Staple in Daydreamer’s Stripes

The thing that we think really hits home about our collection is the multiple seasonal and unexpected colorways that speak to both the striped sweatshirt’s classic charm and modern appeal. Perfect for embracing all that comes with fall, these designs were applied to two of the brand’s most iconic oversized styles: the half-zip sweatshirt and vintage sweatshirt, so you know it’s going to feel just-right. Crafted in soft cotton fleece, the vintage-inspired silhouettes are perfect for layering as a transitional weather piece. We wanted to offer you not only cool garments, but wardrobe staples that you’ll find yourself reaching for again and again. Whether you’re dressing it up or keeping it casual, there is a striped sweatshirt for you that your cozy fall outfits are going to love.

Let’s be real—fall fashion wouldn’t be what it is without a comfy, cozy sweatshirt that feels as good as it looks.

We’re welcoming in the season that invites us to not only get playful with our layers, but pull out some of the most comfortable things in fashion. Daydreamer’s oversized striped sweatshirts are created to be the ultimate go-to. With endless fun ways to style them, these are the kinds of pieces that will quickly become your wardrobe staples and stay eagerly waiting to greet you for many seasons to come. Whether you’re heading to a casual brunch, the office, running errands, or just lounging at home, you can’t go wrong with cozy striped sweatshirts. So when it comes to styling, go ahead and play around with mixing them with tailored, short, or loose silhouettes. Throw it around your shoulders in the warm early evenings, toss it over anything as the sun goes down and the night cools, and just roll with it. Don’t forget to accessorize in a way that’s you, and you’ll find your very own striped sweatshirt sweet spot. We think you’ll find it’s always a look! So maybe, if you think about it, the best time to wear a striped sweatshirt really is all the time…