Fall Break Outfit Ideas: What to Wear for City, Mountains & Beyond

Fall Break Outfit Ideas: What to Wear for City, Mountains & Beyond

Fall Break is the perfect time to recharge, explore, and spend time away. But figuring out what to pack can sometimes feel like the hardest part. That’s where the right fall break outfit ideas come in. Whether your plans involve crisp mountain air, bustling city streets, or somewhere in between, the key is choosing versatile, stylish pieces that keep you feeling confident and comfortable. To make things easy, each of our stylists created two looks — complete with notes on why they work — so you’ll have plenty of inspiration for what to wear on your getaway.

Fall Break Outfit Ideas: The Effortless Matching Set

Katie: A matching set is a smart choice for fall break. It’s equal parts comfortable and put-together, making it ideal for travel or downtime. The lightweight layers give you flexibility! Keep the hoodie on for cooler temps or tie it around your waist if the weather warms up.

Fall Break Outfit Ideas: The Effortless Matching Set | Lightweight layers give you flexibility—keep the hoodie on for cooler temps or tie it around your waist if the weather warms up.

Full Zip Hoodie | Wide Leg Sweatpants | Knit Jersey Tank | Brown Sneakers | Crossbody Fanny Pack | Sunglasses | Cotton Canvas Baseball Cap

Fall Break Outfit Ideas: Easy, Polished Casual for Your Getaway

Dana: A bermuda short look is a safe bet when packing for fall break. You can pair with a t shirt and layer under a suede jacket if the temps drop. Pair with a flat shoe, a suede bag and you have a chic daytime, weather appropriate fall look.

Fall Break Outfit Ideas: Easy, Polished Casual for Your Getaway | A bermuda short look is a safe bet when packing for fall break. Pair with a t shirt and layer under a suede jacket if the temps drop. Pair with a flat shoe, a suede bag and you have a chic daytime, weather appropriate fall look.

Suede Crop Jacket | Striped Tee | Denim Bermuda Short | Mary Jane Flats | Suede Bucket Bag | Sunglasses | Metallic Leather Belt

Katey: Layering is key when traveling for fall break. A sweater draped over your shoulders completes the look but is practical when the day starts super chilly. Pairing chocolate and ivory and chambray is a sharp combination that works for any destination – the city or the mountains. Ditch the sweater and opt for a flat to have the look translate to a fall beach destination.

Layering is key when traveling for fall break. A sweater draped over your shoulders completes the look but is practical when the day starts super chilly. Pairing chocolate and ivory and chambray is a sharp combination that works for any destination - the city or the mountains. Ditch the sweater and opt for a flat to have the look translate to a fall beach destination.

Stripe Pullover Sweater | Relaxed Denim Shirt | Wide Leg Jeans | Brown Sneakers | Tote Bag | Leather Belt

Katie: An oversized cardigan layered over a tank and relaxed denim is the kind of effortless combo that works whether you’re traveling for fall break or enjoying a laid-back day at home. The cardigan adds cozy versatility—wear it when temps dip or simply toss it over your shoulders if it’s still warm—while the woven flats and layered accessories keep the look stylish without sacrificing comfort.

An oversized cardigan layered over a tank and relaxed denim is the kind of effortless combo that works whether you’re traveling for fall break or enjoying a laid-back day at home. The cardigan adds cozy versatility—wear it when temps dip or simply toss it over your shoulders if it’s still warm—while the woven flats and layered accessories keep the look stylish without sacrificing comfort.

Cocoon Cardigan | Scoop Neck Tank | Straight Leg Jeans | Woven Mary Jane Flats | Suede Shopper Bag | Sunglasses | Layered Necklace

Fall Break Outfit Ideas: From Day to Dinner in Style

Dana: A simple black dress is a no brainer for fall break. Layer a light weight tech jacket over it if the weather is chilly. Pair with a fashion sneaker and some gold accessories. This is an easy fall transitional look for any fall break destination.

Fall Break Outfit Ideas: From Day to Dinner in Style | A simple black dress is a no brainer for fall break. Layer a light weight tech jacket over it if the weather is chilly. Pair with a fashion sneaker and some gold accessories. This is an easy fall transitional look for any fall break destination.

Cropped Jacket | Black Column Dress | Neutral Sneakers | Mini Tote Bag | Cat Eye Sunglasses | Gold Hoop Earrings

Katey: Choosing a dress that can be worn multiple ways is a great choice when traveling for fall break. I’ve styled this look for a dinner out, but you could easily opt for a flat shoe for a more casual daytime look.

Choosing a dress that can be worn multiple ways is a great choice when traveling for fall break. I've styled this look for a dinner out, but you could easily opt for a flat shoe for a more casual daytime look.

Charcoal Dress | Knee High Boots | Leather Shoulder Bag | Gold Statement Earrings | Gold Chain Bracelet

No matter where your fall break takes you, having a few well-planned outfits makes travel more enjoyable and stress-free. If you’re ready to simplify your packing process, build a versatile wardrobe, or create a closet that feels effortless season after season, our team of personal stylists is here to help. From curated travel wardrobes to full closet edits, we’d love to take the guesswork out of getting dressed. Learn more about our personal styling services here!

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