
Hello my adventurous friends, Emily here! There’s nothing quite like a fall getaway. The changing leaves, the cozy vibes, the promise of a new adventure it’s pure magic. But let’s be honest, the thought of packing and figuring out what to wear can quickly dampen the excitement, especially when you want to feel both comfortable and chic.
As a curvy woman, you deserve travel outfits that work as hard as you do. You need pieces that are comfortable for long journeys, stylish enough for destination photos, and versatile enough to mix and match into multiple looks. Forget sacrificing style for comfort; this fall, you can have it all.

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I’ve curated 14 plus size fall travel outfits that prioritize ease, flatter your curves, and make getting there just as enjoyable as arriving. Let’s pack your suitcase with confidence!
Why Your Travel Wardrobe Needs a Strategy
Travel fashion is a different beast. It’s not just about looking good; it’s about practicality, comfort, and versatility. The perfect travel outfit for curvy women includes:
- Stretch and Give: Fabrics with a bit of elastane or natural give (like ponte knit and jersey) are essential for comfort during long sits.
- Layering Potential: Fall weather is unpredictable. Light, packable layers are your best friend for adapting to changing temperatures.
- Wrinkle-Resistant Fabrics: Choose materials that look fresh after being folded in a suitcase or worn on a long flight.
- Confidence: Ultimately, you want to step off a plane or out of a car feeling put-together and ready to take on your adventure.
Your Travel Style itinerary: 14 Curated Outfits
I’ve designed these outfits for every leg of your journey, from the travel day itself to exploring your destination in style.

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I. The Journey There: Plane, Train, or Automobile
These looks are designed for maximum comfort without compromising on style.
1. The Ponte Knit Jogger Set

Elevate loungewear with a matching set made from high-quality ponte knit. This fabric feels like sweatpants but looks polished and sleek. Pair with a cozy cardigan and stylish sneakers for an outfit that transitions seamlessly from the airport to a casual lunch.
2. The Stretchy Midi Dress & Cardigan

A stretch jersey or ponte knit midi dress is a one-and-done wonder. Layer a long, lightweight cardigan over it for easy temperature control. This look is effortlessly chic and requires zero effort once you arrive.
3. The Legendary Leggings & Tunic Combo

This classic is classic for a reason. The key is in the details: choose thick, opaque ponte leggings and a long, knee-length tunic that provides full coverage. Add a blanket scarf that can double as a pillow and comfortable slip-on shoes.
II. Exploring Your Destination: Comfort Meets Curiosity
These outfits are for days filled with walking, sightseeing, and making memories.
4. The Utility Jogger & Graphic Tee

Utility joggers offer the comfort of sweatpants with a more structured, stylish look. Pair them with a soft graphic tee and a lightweight denim jacket for a cool, casual ensemble perfect for exploring a new city.
5. The Corduroy Shirtdress

A corduroy shirtdress is a fall travel superstar. It’s comfortable, on-theme for the season, and can be belted for definition. Wear it with ankle boots and tights if it’s chilly, or with sneakers on a warmer day.
6. Dark Denim & a Striped Top

You can never go wrong with well-fitting dark wash jeans and a classic striped breton top. It’s a timeless combination that works anywhere in the world. Layer with a scarf and a crossbody bag for a quintessential Parisian-explorer vibe.
7. The Sweater Dress & Boots

A fitted sweater dress is cozy and chic for crisp fall days exploring quaint towns. Pair it with knee-high or over-the-knee boots for extra warmth and a touch of sophistication.
III. Versatile Layers: Your Travel Wardrobe Heroes
These pieces are the glue that holds your travel capsule together.
8. The Lightweight Trench Coat

A classic trench coat is the ultimate travel layer. It elevates every outfit underneath, is perfect for drizzly weather, and can be easily folded without major wrinkling.
9. The Cozy Oversized Blazer

An oversized blazer is surprisingly versatile. Wear it over a dress for dinner, with jeans and a tee for a museum day, or even layered over pajamas for a quick trip to the hotel lobby.
10. The Quilted Vest

A quilted vest is perfect for adding core warmth without restricting your arms. It looks great layered over long-sleeve tees, sweaters, and flannels, making it a key piece for creating multiple looks.
IV. Dinner & Evening Looks: Effortlessly Elevated
Transform your day looks into evening-ready outfits with a few smart tweaks.
11. The Silky Slip Skirt & Sweater

Pack a satin slip skirt it takes up almost no space! During the day, you might wear jeans. For evening, pair the skirt with a simple cashmere-style sweater and heeled ankle boots for an outfit that is both comfortable and elegant.
12. Statement Pants & a Simple Top

A pair of wide-leg trousers in a bold pattern or color can be the foundation of your evening looks. Pair them with a simple black bodysuit or a fitted knit top. The statement pants do all the talking.
13. The Versatile Jumpsuit

A jumpsuit in a wrinkle-resistant fabric is a powerful one-piece wonder. Dress it up with statement earrings and a wedge heel, or dress it down with a denim jacket and sneakers during the day.
14. The Faux Leather Leggings

Faux leather leggings are a travel game-changer. They feel like leggings but look incredibly chic. Wear them with an oversized sweater and booties for a dinner look that is both edgy and comfortable.

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Emily’s Pro Tips for Stress-Free Travel Style
- Choose Your Travel Shoes Wisely: You will walk more than you think. Supportive fashion sneakers, comfortable ankle boots with a block heel, and stylish flats are must-packs. Never wear brand-new shoes on a travel day!
- Embrace a Color Palette: Pack pieces in a cohesive color scheme (e.g., navy, grey, burgundy, and cream). This ensures everything mixes and matches effortlessly, giving you more outfit options with fewer items.
- Accessorize Strategically: A large scarf is a multitasker it’s a blanket on the plane, a wrap for a chilly restaurant, and a style accessory. A crossbody bag keeps your hands free and your belongings secure while exploring.
- Compression Socks are Secret Weapons: For long flights or car rides, don’t underestimate the power of cute compression socks hidden under your pants or leggings. Your circulation will thank you.
Adventure Awaits in Comfort and Style
Remember, lovelies, the goal of your travel wardrobe is to make you feel confident and free to enjoy every moment of your journey. When you feel good in what you’re wearing, you can focus on the experiences, not your outfit.

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Which of these plus size fall travel outfits are you packing for your next adventure? Share your own travel style hacks and favorite destinations with our community over on Pinterest. Tag @chicseasonstyle so we can see your amazing travel looks and share the inspiration!