Outfit Ideas for Fall Getaways
From wine country weekends to pub hopping across England, here’s what to pack for your next trip!
I’m off to France, England and Italy for my first trip of the Fall season, and while I’m hopeful for summer weather, as soon as I return home I know I’ll be looking forward to turning over my closet and reuniting with all my favorite sweaters, jeans and blazers.
Whether you’re sneaking away for a cozy countryside escape (Carly and I have our annual upstate New York trip planned for next month), or hopping across the pond to fill your days with crisp strolls and café stops, the outfits you pack can set the tone for the entire trip.
This time of year I love leaning into seasonal textures and colors (think plaids, knits, and rich neutrals) that feel instantly autumnal but still versatile enough to style multiple ways. Today I’m rounding up outfit ideas to inspire your next Fall getaway so you can spend less time staring at your suitcase and more time enjoying an extra glass of red by the fire!
Housekeeping note: This post is too long for email. Please enjoy it in the Substack app or on your desktop.
Chic Outfit Ideas for Fall Getaways
A fall getaway to California wine country calls for a comfortable (but chic) dress that can take you from wineries straight to dinner! This chocolate brown swing midi dress is made from the most luxurious thick fabric plus it packs beautifully. Add cognac suede boots and this mini bag under $150 that could both be re-styled with other items in your suitcase. Small gold earrings and oval sunnies complete the look.
I may or may not have packed nearly this exact outfit for my trip.
You truly can’t go wrong with satin trousers and a cardigan for a chic monochromatic looks. Leset is a newer-to-me brand that I’ve been loving, and of course Jenni Kayne makes some of my all time favorite knits. (A note on sizing for this cardigan, if you plan to wear it buttoned-up as a top I suggest sizing up at least one size.) I almost always have my favorite Dorsey jewels with me including these drop earrings and this necklace. Add a petite bag, classic cap toe flats, and of course a coat of Parisian inspired red lipstick!
As I mentioned, I already have my annual Fall trip to upstate New York on the calendar and I’m seriously counting down the days. I missed the annual highlight last year so I am very overdue. Give me all the maple lattes and apple cinnamon scones. There’s nothing like the foliage upstate, especially if you can time it right. This budget-friendly quilted jacket is the perfect topper for jeans and a classic crewneck sweater. I swear by my Freda Salvador boots (use code WITWHIMSY10 now OR wait till 8 am pst on 9/23 and use code FREDAFAMILY for 20% off)), but these are another solid option under $200. Don’t forget a beanie for chilly mornings!
Is there anything more perfect than afternoon tea beside a roaring fire? When you want to dress up but still be warm, I love pairing a silk slip skirt with a matching cardigan for a monochromatic moment. Add tall boots for additional warmth, and a matching suede shoulder bag. Don’t forget a little sparkle, by way of my beloved Dorsey bezel bracelet and simple gold hoops.
A trench coat is a must-pack item for me, especially when I’m traveling to England or France in the Fall. The weather can be unpredictable and I’m always grateful to have this versatile layer in my suitcase. For a day full of walking and treasure hunting, keep things comfortable with these Varley trousers that drape beautifully plus an oversized sweater tee. My favorite Veja sneakers and this Mansur Gavriel tote that I own in a different hue complete the look, along with a versatile necklace and these earrings I own and love (use code DONOVAN15).
Sunday roast in England is practically mandatory, it’s basically the English’s version of our Sunday brunch but less sweet and far more savory. This plaid barn jacket was made for an English countryside getaway (wearing a M HERE), as was my beloved Jenni Kayne cashmere fisherman sweater (use code MEGHANDONO10). These jeans have become a favorite style of mine, and I would add sporty chocolate brown sneakers and this slouchy tote under $100.
If you’re finding yourself stateside for Sunday brunch, I’m obsessed with this sleek ladylike look. This tweed jacket under $150 (that also comes with matching shorts) was my inspiration, I love tan paired with cream in the Fall so I opted for wide leg jeans from L’Agence. Keep things neutral with Margaux’s brand new ballet flat and my forever favorite crossbody from Demellier. Petite diamond huggies and a simple gold watch (use code DONOVAN15) are the perfect understated but elegant accessories.
There’s nothing more quintessentially Fall than apple picking (especially when there are apple cider donuts involved)! This casual look outfit could work for a variety of occasions because it relies on a relatively simple outfit formula — jeans and a sweater (that I just bought bc of course I did). From here, you can keep things relaxed with a wool blend swing coat, block heel boots, and a budget-friendly bucket tote. Alternatively you could dress this up by adding a dressier boot and purse, and opting for a long wrap coat.
Hope you enjoyed this post! Thank you so much for reading!
🫶🏻 If you enjoyed this post, please click the like button at the bottom - it helps others discover my content and is an easy way to support my work! Or, consider sharing it with someone you think might enjoy.
✨ For more of content this, follow me on Instagram, or check out my blog, wit & whimsy!
This post contains affiliate links. Should you purchase something from an affiliate link, I may earn commission, at no cost to you. Thank you for your support of my work!