
Hello, my stylish friend! Emily here from Chic Season Style. As the leaves begin to turn and that crisp autumn air rolls in, I know many of us are dreaming of a perfect fall getaway. And with travel comes the big question: what to pack?

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I believe your vacation wardrobe should make you feel as fabulous as the destination itself. It’s all about embracing your curves with confidence and choosing pieces that are equal parts comfortable and chic. Forget the stress.
I’ve curated 15 plus size fall vacation outfits that curvy women truly love, from city strolls to cozy mountain retreats. Let’s build a travel capsule that celebrates you.
Building Your Plus Size Fall Vacation Capsule Wardrobe
The secret to these 15 outfits is a curated capsule of versatile, mix-and-match pieces. Start with a foundation of rich autumn hues like olive green, burgundy, camel, and navy, alongside classic neutrals.
The Non-Negotiable Packing List
- The Perfect Jeans: A dark wash skinny or straight-leg style.
- Comfy Ankle Boots: A low block heel or flat style.
- A Versatile Midi Skirt: Your go-to for dressing up or down.
- Layerable Tops: Long-sleeve tees, bodysuits, and a classic button-down.
- Statement Outerwear: A trench coat, leather jacket, or cozy blazer.
15 Plus Size Fall Outfits You’ll Want to Pack Immediately
Here are 15 effortlessly chic outfit formulas for your next autumn adventure.
City Strolling & Café Hopping
Perfect for exploring charming streets and enjoying a latte.

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1. The Effortless Classic

High-waisted dark wash jeans, a fitted long-sleeve bodysuit, and a tailored trench coat. Accessorize with ankle boots and a crossbody bag.
2. The Polished Casual

A sleek ponte knit dress layered under your leather jacket. Add tights and heeled booties for a perfect dinner-to-drinks look.
3. The Modern Twist

Wide-leg trousers paired with a simple turtleneck and a statement belt. Finish with loafers for a touch of sophisticated flair.
Cozy & Casual Day Trips
Ideal for pumpkin patches, apple picking, or scenic drives.
4. The Comfort King

A pair of ultra-soft, high-quality leggings with an oversized, chunky knit sweater and cozy sneakers.
5. The Rustic Charm

Corduroy pants in a warm tone (like camel or rust) paired with a graphic long-sleeve tee and your favorite ankle boots.
6. The Layering Pro

A flannel shirt tied over a solid-colored tee, paired with jeans and sturdy yet cute booties for a day of exploration.
Elevated Evening Dinners
For those special nights out that call for something more.
7. The Dinner Date

A beautiful wrap dress in a fall floral or solid color, paired with heeled booties and statement earrings.
8. The Edgy Romantic

A flowy midi skirt with a sleek bodysuit and your leather jacket. Define your waist with a thin belt.
9. The Modern Elegance

A satin slip skirt with a tucked-in cashmere sweater and delicate gold jewelry.
Unexpectedly Warm Days
For when the autumn sun surprises you.
10. The Transitional Dress

A shirt dress in denim or corduroy, worn belted with ankle boots or layered over a tee.
11. The Skirt & Sweater Combo

A breezy A-line skirt with a lightweight, fitted sweater and sneakers for a comfortable, stylish look.
12. The Classic Redux

Cuffed jeans, a breezy button-down shirt left untucked, and flat mules.
Outdoor Adventures & Scenic Views
Comfort meets style for active days.
13. The Practical Chic

A sturdy pair of jeans, a thermal top, a utility jacket, and comfortable hiking boots that still look great.
14. The Cozy Lodge Look

A thick, cable-knit tunic sweater over leggings with warm socks and duck boots.
15. The Stylish Sightseer

A comfortable sweater dress, layered with a puffer vest and topped with a beanie and combat boots.

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Key Plus Size Styling Tips for a Flawless Fit
Embrace Tailoring: A small adjustment, like taking in a waist, can make a piece look custom-made.
Define Your Waist: Use belts or tucked-in tops to highlight your silhouette. This is a game-changer for creating shape.
Play with Proportions: Balance voluminous pieces (like an oversized sweater) with fitted bottoms (like leggings or skinny jeans).
Pack Your Confidence First
The most important accessory you can pack is your confidence. These 15 plus size fall vacation outfits are a starting point for you to build upon. Choose pieces that you love and that feel authentically you.

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I hope this guide inspires you to pack a suitcase full of outfits that make you feel unstoppable. Which look is your favorite? Share your vacation style with our community over on Pinterest by tagging @ChicSeasonStyle. We love seeing how you bring these ideas to life!
Happy travels, and remember to own your look!