Cool mornings, early sunsets, and the first excuse to unpack the sweaters. Fall makes getting dressed feel like a treat. It’s the season when layers stop being about personal style and start to become practical. And no matter what’s on your calendar, apple picking, game days or just the weekly pumpkin run, there’s no shortage of chances to look pulled together.
This guide has everything you need to plan fall outfits that feel current without chasing trends. From smart layering tricks to timeless pieces that work all season, we’ve mapped out what’s best for every fall activity worth leaving the house for. Let’s get into it.
Ready for Fall Festivals
Fall festival season is here, and so are those tricky in-between days—sunny one minute, chilly the next. Lands’ End has the perfect layers ready. Our soft flannel shirts and jeans with a little stretch give you a solid foundation for apple picking, corn mazes, or just navigating the kettle corn line. Bring a packable vest for all the warmth and none of the bulk; easy to stow away when the sun does its thing. And don’t forget a sturdy shoe or boot to keep you steady on muddy paths while looking good enough for that impromptu festival photo op.
What makes Lands’ End your go-to for fall adventures? We design with your real life in mind. Our easy-care fabrics stay fresh-looking even after an afternoon on hay bales. Pockets actually fit your phone and festival map (imagine that). And our legendary durability means this year’s fall favorites will be ready for next autumn’s adventures too. With sizes that fit everyone, the whole family can enjoy the day in comfort. Because at Lands’ End, we’re not just selling clothes—we’re equipping you for whatever your autumn journey brings, from that first pumpkin patch visit to the last cider donut of the season.
Our Festival Favorites:
- Boyfriend Fit Long Sleeve Flannel Shirt
- Wanderweight Packable Down Vest
- Soft Denim High Rise Straight Leg Utility Jeans
- Classic Leather Chelsea Boots
Apple Orchard
Ready for apple orchard adventures? Layer up with a super-soft Supima Cotton Turtleneck beneath an ultralight Wanderweight packable vest - your companions for the day as temperatures journey from crisp morning air to golden afternoon warmth. Pair with your favorite skinny jeans for a slender profile, and which feature a touch of stretch so you can reach the very best apples. You’ll appreciate that these garments maintain their quality season after season - that’s the kind of value we believe in.
Navigate orchard terrain with confidence in women’s shoes that offer plenty of support and coverage - try a slip on sneaker or short boot. Water-resistant suede and grippy soles mean you won’t think twice about morning dew or uneven ground - you’ll be too busy enjoying the day. Don’t forget the versatile Lands’ End canvas tote bag to stow away your packable vest, and for all your apples and gift shop delights. The vest adds warmth without bulk when the breeze picks up, while the bag keeps essentials at hand but your hands free for what matters. These pieces are built to last, so you can focus on making memories, not replacing your gear.
Try These Fresh Picks:
- Supima Cotton Fitted Turtleneck
- Wanderweight Belted Packable Down Vest
- High Rise Slimming Jeans
- Zip Up Ankle Boots
- Canvas Market Tote
Pumpkin Patches
A perfect day of pumpkin picking requires the perfect layers. Nothing screams farm-ready like our classic flannel, but we’ve been there already. A cozy hoodie or Anyweather fleece will keep you comfortable on cool mornings but can be easily tied around the waist as the sun warms in the afternoon. Try an ultra-soft Supima tee or cotton tank top underneath. A Squall packable rain jacket stows away in your tote or purse but you won’t regret bringing it along when the weather turns unexpectedly. This dynamic jacket shrugs off unexpected showers while keeping chilly breezes at bay, so you can focus on finding that perfect orange treasure instead of worrying about the weather.
Relaxed fit jeans are a natural fit for the outing, moving with you through corn mazes and hayrides while standing up to whatever the day brings. Pair them with some all-weather footwear - because muddy fields and dewy grass are no match for footwear designed with autumn adventures in mind. Like the changing seasons themselves, these Lands’ End essentials are crafted to last year after year, becoming trusted favorites that only get better with time.
Our Picks for the Patch
- Serious Sweats Full Zip Hoodie
- Cotton Tank Top
- Squall Packable Rain Jacket
- Relaxed Barrel Leg Ankle Jeans
- Insulated Duck Boots
Hayrides and Corn Mazes
When hayride season arrives, you’ll want gear that handles both the festive fun and the unpredictable weather. Our women’s coats & jackets offer a range of weatherability from windproof, to water resistant, to fully waterproof while maintaining breathability—perfect for those crisp country afternoons when clouds might roll in. Underneath, a Serious Sweats® Crewneck provides reassuring warmth without bulk, giving you the mobility you need to climb aboard that wagon with ease.
For comfort you can count on, our Flannel-Lined Straight Leg Jeans offer the perfect solution—classic denim on the outside that stands up to hay and rough surfaces, with soft flannel on the inside that keeps warmth where you want it. Give your feet a break from bumpy terrain with our All Weather Mocs, featuring weather-resistant suede and cushioned footbeds that transform uneven paths into smooth journeys.
Complete your outfit with practical accessories that earn their keep: a CashTouch Scarf that delivers remarkable softness at an honest value, and EZ Touch Gloves with Thermoplume insulation that let you use your phone without exposing fingers to the chill. Each piece is backed by our legendary quality guarantee, ready to join you on this autumn journey and many more to come.
Ride in Comfortable Style:
- Serious Sweats® Crewneck Sweatshirt
- High Rise Straight Leg Blue Jeans
- Squall Hooded Waterproof Raincoat
- John Deere Medium Tote Bag
- Zip Up Leather Lug Boots
Fall Foliage Trip
Ready for leaf-peeping season? Smart layering is essential to help you weather crisp mornings and sunny afternoons without missing a moment of autumn’s show. Try an ultra-soft Supima cotton turtleneck as your base layer - it’s soft against your skin but tough enough for a day of exploration. Add a no-bulk fleece vest for core warmth, and keep a water-resistant Squall jacket handy for those surprise mountain showers. Complete your road-trip-ready outfit with a pair of pull-on pants or leggings and a some slip-on sneakers; covered for any adventure and comfy enough for the car ride.
We design our clothing and apparel with your real adventures in mind - whether you’re touring Vermont’s famous foliage or just strolling through your neighborhood park. Lands’ End quality means these fall favorites will be in your rotation for years, not just seasons. The reinforced seams won’t quit when you stretch for that perfect vista photo, and our quick-drying fabrics keep you comfortable when the trail gets steep. Plus, everything works together without much thought, so you can pack lighter and still be prepared for whatever your autumn journey brings. That’s the Lands’ End difference: practical solutions that let you focus on the memories, not your clothes.
Find Your Colors:
- Long Sleeve Micro Rib T-Shirt
- Sweater Fleece Vest
- Starfish High Rise Pants
- Casual Knit Slip-on Sneakers
- Candie’s Plastic Round Sunglasses
Game Day Ready: Your Tailgate Essentials
Ready for game day? Our versatile Squall jacket is your most reliable sideline companion, adapting to unpredictable fall temperatures while easily shedding when the afternoon sun breaks through. Weather forecasts can be as unreliable as first-quarter predictions, but your outerwear never will be. An Anyweather fleece in team-inspired colors provides that just-right layer of warmth without bulk, while our Wide leg, straight or relaxed fit jeans offer the freedom of movement needed when jumping up for that crucial play. These aren’t just clothes, but practical solutions that perform with the same dependability as your favorite game day traditions.
The right accessories turn a long day of tailgating from an endurance test into an enjoyable celebration. The classic Lands’ End tote bag holds everything from extra layers to those homemade treats your friends have come to expect. Comfort First sneakers keep you supported through hours of standing and cheering, while a team-colored CashTouch scarf adds both warmth and spirit as temperatures drop after sunset. What makes these Lands’ End pieces essential team players? Their exceptional quality and thoughtful design ensure they’ll be ready for next season’s opening kickoff and every game thereafter. These are investments that keep their shape and quality season after season, ready for every game on your schedule.
Pre-Game Parties to Post-Game Celebrations:
- Anyweather Fleece Quarter Zip Pullover
- Soft Denim Mid Rise Relaxed Straight Leg Jeans
- Squall Waterproof Slicker Raincoat
- Rubber Chelsea Rain Boots
- Water Resistant Packable Tote
Plus and Petite
Your fall adventure begins here, with clothing thoughtfully designed for petite and plus-size women who refuse to let sizing dictate their outdoor experiences. Consider our cozy sweatshirts & hoodies tailored to flatter petite and plus size frames, or thermal henleys that stretch in all the right places. A great adventure wardrobe includes pants with just-right inseams and comfort waistbands that stay put when you’re scrambling over that fallen log. Our weather-anything Squall jackets come in all size ranges as well - plus size Squall for extra room in all the key locations and petite Squall for a compact frame without the extra material. At Lands’ End you don’t have to be creative to find a wardrobe that fits, we’ve designed the perfect fit that works for you in all seasons!
Your fall journey deserves more than just great clothes, which is why we have thoughtfully designed everything else you will need too. Our famously durable canvas totes and backpacks offer intelligent organization with pockets perfectly placed for quick access. Wrap yourself in scarves and gloves that complement rather than overwhelm petite wrists or comfortably accommodate plus-size hands.
What sets Lands’ End apart? It is our promise that inclusive sizing never means compromising on function. Those reinforced seams remain steadfast when you’re reaching for the perfect apple at the orchard, and fabrics tested in Wisconsin winters—where we know a thing or two about weather—mean you’ll feel prepared, not just dressed, for life’s every journey!
Frequently Asked Questions
There’s no shortage of ways to style fall outfits, but some pieces get overlooked in the shuffle. Here are a few quick answers to help confidently round out your wardrobe.
Can I wear dresses in the fall without freezing?
Yes. Dresses can be a great option for fall. Look for long-sleeve knit dresses, sweater dresses, or shirt dresses in heavier fabrics like ponte or brushed cotton. Pair them with tall boots and fleece-lined tights for warmth without sacrificing style.
What outerwear works for unpredictable weather?
A packable Squall jacket or a water-resistant barn coat has your back when the forecast can't make up its mind. You'll stay dry and warm without lugging around a full parka.
What's a good layering strategy for early fall?
Stick to three layers: a base layer (like a tee or turtleneck), a mid-layer (sweater, flannel, fleece) and an outer layer (vest or jacket). That way, you can add or shed pieces as the temperature swings.
How do I dress up fall outfits for work or dinner out?
Swap sneakers for ankle boots, add a structured coat and pick accessories with texture. Tailored pants or a sleek midi skirt instantly pull the look together.
Are there any fall outfit ideas that don't involve jeans?
Absolutely. Corduroy trousers, ponte knit leggings, midi skirts and sport joggers are all solid alternatives that hold up in cooler weather and don't feel too casual.
Find Fall Outfits That Fit Your Lifestyle
Embrace fall with Lands’ End—where cozy comfort meets practical design. Our water-repellent jackets and versatile layers adapt to shifting temps, while inclusive sizing and smart details like extra pockets and adjustable hoods ensure you’re ready for anything. Built to last and made to empower, our outerwear helps you greet each autumn day with confidence. Discover the collection and see why preparedness has never felt so good.
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