Ten stylish fall outfits for a weekend getaway

Fall outfits

top 10 fall outfit ideas for a weekend getaway

By Autumn Lee

Published: 05 May 2025

A Spontaneous Weekend Escape

Okay, so picture this: it's Friday afternoon, and I'm staring blankly at my overflowing inbox, feeling utterly drained. Suddenly, a message pops up from my best friend, Sarah. 'Weekend getaway? Napa Valley?' she asks. My initial reaction? Total panic! But then... that tiny voice of adventure inside me whispered, 'YES.' And that's how, dear reader, I ended up spontaneously ditching my to-do list for a whirlwind weekend exploring California wine country. This got me thinking: how do you pack perfectly for a spontaneous trip? Less is way more, especially when you’re not sure what adventures await. So here are my top ten fall outfit ideas that are both stylish and surprisingly versatile – perfect for everything from vineyard hopping to cozy nights by the fireplace.

woman packing a stylish weekend bag

woman packing a stylish weekend bag | Image: Supplied

1. The Cozy Cardigan Combo

This is my go-to. A chunky knit cardigan (think soft wool or cashmere—splurge a little; you deserve it!), paired with a simple white tee, dark-wash jeans, and ankle boots. It's effortlessly chic, comfortable enough for long walks amongst the vineyards, and easily layered if the evening gets chilly. Plus, a cardigan instantly elevates even the simplest jeans-and-tee combo. Think of it as your stylish security blanket for any unexpected temperature drops. What are some cozy cardigans in your wardrobe you love to take on trips?

woman wearing a cozy cardigan and jeans in a vineyard

woman wearing a cozy cardigan and jeans in a vineyard | Image: Supplied

2. The Flowy Dress and Boots Ensemble

A midi-length flowy dress, maybe in a rich jewel tone like emerald green or deep burgundy, looks amazing with knee-high brown leather boots. This outfit screams fall fashion. Add a long, delicate necklace and a crossbody bag, and you're ready to sip wine and soak up the scenery. It also transitions well for dinner. Just throw on a leather jacket for extra warmth and some edge. If you want to elevate this look, add a statement belt to define your waist and create a more flattering silhouette. How about adding a pop of color to this look with a scarf or handbag? What color would you add?

woman in a flowy dress and boots in a fall setting

woman in a flowy dress and boots in a fall setting | Image: Supplied

3. The Layered Look: Leather Jacket & Turtleneck

Leather jackets never go out of style! Pair a classic black leather jacket over a cozy turtleneck (cream or gray work perfectly), slim-fitting jeans or leggings and stylish ankle boots or sneakers for a touch of edgy elegance. This is the outfit for a little city exploring during your weekend getaway. To accessorize, add some statement jewelry or a cool beanie if it's a bit windy. It looks effortless, chic and makes you feel very put together, even if you’re just grabbing coffee before a hike! Do you prefer leather jackets or other outerwear options for fall?

woman wearing a leather jacket and turtleneck in a city setting

woman wearing a leather jacket and turtleneck in a city setting | Image: Supplied

4. The Chic Jumpsuit

Jumpsuits are the ultimate time-saver when packing light. Find one in a stylish fabric like corduroy or velvet—it will make you look effortlessly put together, even when rushing to get ready. Accessorize with a statement belt, delicate gold necklace, and a pair of stylish flats or boots. This outfit is a great option for daytime activities as well as evening outings. If you want to dress it up, opt for a heeled boot. How would you style your perfect jumpsuit?

woman wearing a chic jumpsuit in a fall setting

woman wearing a chic jumpsuit in a fall setting | Image: Supplied

5. The Plaid Shirt Magic

A classic plaid shirt, tied around your waist, adds an instant touch of casual chic to any outfit. Throw it over a simple dress, wear it with jeans and a t-shirt, or pair it with leggings and boots – the possibilities are endless! It’s a great layering piece for fluctuating temperatures. What is your favorite way to use a plaid shirt?

woman wearing a plaid shirt tied around her waist

woman wearing a plaid shirt tied around her waist | Image: Supplied

6. The Statement Sweater

Invest in a statement sweater with interesting textures or patterns—cable knit, chunky knits, or Fair Isle designs are all fantastic choices. Pair it with skinny jeans, leggings, and your favorite boots for a look that's both warm and stylish. The statement sweater is a great way to add personality to your fall outfit. Don’t forget to choose a color that flatters your skin tone. Do you prefer cardigans or pullovers in the fall?

woman wearing a statement sweater with skinny jeans

woman wearing a statement sweater with skinny jeans | Image: Supplied

7. The Versatile Scarf

Scarves are my secret weapon for adding warmth and style to any outfit. A large, cozy scarf can transform a simple dress into a stylish ensemble, or add a pop of color to an otherwise neutral look. Plus, they're easy to pack! I prefer a lightweight scarf that’s easy to layer, but it really depends on how cold you get. What is your go-to scarf style for fall?

woman wearing a large, cozy scarf

woman wearing a large, cozy scarf | Image: Supplied

8. The Comfortable Boots

Choose comfortable yet stylish boots—ankle boots, knee-high boots, or even stylish sneakers are great choices. Comfort is key, especially if you plan on doing a lot of walking. Make sure your footwear is also waterproof or water-resistant in case of unexpected rain showers. What is your favorite type of boots to wear during fall?

woman wearing comfortable boots while walking

woman wearing comfortable boots while walking | Image: Supplied

9. The Stylish Leggings

Don’t underestimate the power of leggings! Pair them with a tunic, sweater, or even a dress for a comfortable yet stylish look. They are great for layering, which is essential during the fall and even for layering over your swimwear if you plan to visit hot springs! Leggings are a wardrobe essential. What style of leggings do you prefer?

woman wearing leggings with a tunic and boots

woman wearing leggings with a tunic and boots | Image: Supplied

10. Don’t Forget the Accessories!

A hat, sunglasses, jewelry, and a stylish bag can elevate any outfit. These small details can make a huge difference in your overall look. Choose accessories that complement your outfit and reflect your personal style. What are your fall essentials when it comes to accessories?

So there you have it, my top ten fall outfit ideas for a weekend getaway. Remember, the most important thing is to pack clothes that make you feel confident and comfortable. Now go forth and have an amazing weekend!

woman wearing stylish accessories for a fall outfit

woman wearing stylish accessories for a fall outfit | Image: Supplied

Embrace the unexpected. Adventure awaits!

Want to join our exclusive community?

WordofMany offers general content intended solely for informational purposes. The information provided is not a substitute for professional medical advice, diagnosis, treatment, or financial consultation. Always seek the advice of qualified professionals regarding any medical or financial decisions.

© 2024 Word of Many. All Rights Reserved.