> ## Content Index > Fetch the complete content index at: https://www.tawnymagazine.com/llms.txt > Use this file to discover other available public pages before exploring further. # The Best Fall Trips For Women Who Plan Vacations Around What They Get To Wear - URL: https://www.tawnymagazine.com/the-best-fall-trips-for-women-who-plan-vacations-around-what-they-get-to-wear/ - Published: 2026-10-21T19:21:11.000Z - Updated: 2026-10-21T21:44:22.000Z - Description: From the stables to the city, here are our top fall getaway ideas for the girls who plan the outfits first, book the flights later. - Author: Gentry Hale - Tags: Girls' Trips, Travel, Fall, All Lifestyle Yes, I’m guilty of it. I have planned an entire vacation not based on historical landmarks or cultural immersion, but on a structured, ankle-skimming, gorgeous light camel wool coat that I bought in August and that has been begging me from my closet to take it out. Fall in my hometown of Salt Lake City had been warm and, let's be honest, this coat deserved real admiration. So, a quick flight to JFK put me exactly where it deserved to be, and I strutted around the Big Apple in my gorgeous new jacket for a whole weekend. And no, I am not ashamed to admit that a piece of clothing was the catalyst of my adventure. In fact, this wasn’t the first time that I’d done it. When the summer clothes start hitting the racks in early January (why) and I find the PERFECT swimsuit, I simply have to book a February beach trip to put it to use. But [fall travel](https://www.tawnymagazine.com/the-best-halloween-trips-based-on-your-favorite-halloween-movie/) is elite precisely because it unlocks the most satisfying sartorial category in existence: layers. So, if you are the type to plan your outfits before your itineraries, or you have a new piece of outerwear, footwear, sweater, hell, even a scarf that you're dying to wear, then get your SkyMiles accounts ready. Here are four autumn getaways where the seasonal backdrop exists primarily to elevate your wardrobe choices. --- ## 1\. New York City: The Oversized Vintage Leather Jacket Cool, crisp, and perpetually brisk. Autumn in New York is about cool concrete sidewalks swimming with chic women and well-dressed men, hurrying to their next destination. Most importantly, it is the beginning of coat season. The perfect moment where you don't have to bog yourself down with caps and gloves, but where there is enough nip in the air and enough leaves on the ground in Central Park to elicit your most fabulous coat. A strong outer layer is key here, and oversized vintage leather is all the rage this season. ### What To Do Grab an espresso in SoHo, spend a morning wandering the Chelsea galleries, and stroll down the West Side Highway at sunset. End the night with natural wine at a dim, intimate spot in the Lower East Side where the seating is tight, the music is low, and everyone’s outerwear is on display over the back of their chair. ### Packing & Outfit Inspo This trip demands an oversized, structured vintage leather bomber or a sharp trench coat. Pair it with straight-leg denim, pointed-toe knee-high boots, and a tissue-weight turtleneck underneath. Brands like Anine Bing, Schott NYC, or a scored thrift find from L Train Vintage bring a worn-in architectural edge that matches Manhattan's grid. ![](https://storage.ghost.io/c/5d/7f/5d7fd442-71ad-4570-8922-dc1cc32e7d8e/content/images/2026/10/samuel-regan-asante-P4vdbvY3mNs-unsplash-1.jpg) Photo by [Samuel Regan-Asante](https://unsplash.com/@reganography?ref=tawnymagazine.com) / Unsplash ## 2\. The Pacific Northwest: Chunky Knit Sweaters & Waterproof Lug Soles Fall in the PNW is moody, foggy, Twilight-coded magic. Think warm coffee, overcast skies, ambient drizzle, great shopping, cozy evenings. This applies to Portland, Seattle, or a coastal cabin near Cannon Beach. October and November practically beg for large sweaters, thick graphic crews, boots built for the rain and a killer soundtrack to match the vibe. I am envisioning an alpaca wool sweater over a slip dress for dinner in a dimly-lit room. ### What To Do Drive along the Western coast to catch dramatic autumn foliage through misty mountain passes. Spend rainy afternoons browsing independent bookstores, drinking pour-over coffee, and tucking into warm bowls of soup at local cider houses. Read some poetry, take a walk, chill, stay cute. ### Packing & Outfit Inspo Your goal here is "cozy intellectual". Think heavy, tactile textures—over-proportioned cable-knit sweaters, wool beanies, dark denim, and water-resistant Chelsea boots with a heavy lug sole–even a bright colored Hunter. Reach for heavy knitwear from Dôen, Jenni Kayne, or Free People to nail that relaxed, cabin-ready but curated style. ## 3\. Banff National Park: Puffy-Chic Mountain Outerwear Alpine drama at its absolute peak. Early fall in the Canadian Rockies brings towering granite peaks that will literally take your breath away, and turquoise glacial lakes that reflect the golden larch trees. The landscape is stark, icy, grand, cinematic, and so incredibly perfect for Instagram photos. Style-wise, it is one of my favorites, requiring performance outerwear that can hold its own against towering peaks and crisp high-altitude gusts without sacrificing silhouette. ### What To Do Kick off your morning taking the Banff Gondola up Sulphur Mountain for panoramic alpine views before cozying up over hot cocoa at Sky Bistro. Spend the afternoon taking a premium cruise on the electric-blue Lake Minnewanka, then grab a chic-but-relaxed dinner at Brazen inside of Mount Royal Hotel on the main strip. Relax by the grand fireplace before heading to bed. ### Packing & Outfit Inspo Gorpcore meets high fashion. Swap technical yellow rain jackets for elevated puffy outerwear like cropped glossy down jackets, fleece flecked with rich earth tones, bright prints, beanies, fleece-lined leggings, and heavy-duty shearling-lined hiking boots. Look to Aritzia (specifically The Super Puff), The North Face, or Ganni for statement outerwear that keeps you warm while serving serious peak-side style. My tip? Pack A statement puffer jacket in a deep jewel tone like emerald or burgundy that stands out against gray granite and white snow. ![](https://storage.ghost.io/c/5d/7f/5d7fd442-71ad-4570-8922-dc1cc32e7d8e/content/images/2026/10/ali-atiabii-7I1-PtszrFY-unsplash-1.jpg) Photo by [ali atiabii](https://unsplash.com/@atiabii?ref=tawnymagazine.com) / Unsplash ## 4\. Lexington, Kentucky: Riding Boots & Equestrian Heritage October in Kentucky gives major country-estate energy. I’m talking rolling bluegrass hills framed by fiery oak trees, white paddock fences, walks along the horse pastures in the cool morning air. The whole vibe is refined, quiet luxury, but with a distinctly Southern twist. For outfits, think old money meets Southern charm: tailored, functional, neutral, sharp, chic. ### What To Do Spend a morning touring historic thoroughbred farms (yes, you will want to pet the horses), then head over to the Keeneland Fall Meet for an afternoon of tailgating and live racing. Afterwards, thaw out with a bourbon tasting at a historic distillery along the Bourbon Trail—warm oak interiors and amber spirits around firepits are the perfect place to show off your fit. ### Packing & Outfit Inspo Tailored prep is the move here. Pack your structured tweed blazers, fitted trousers, quilted vests, and sleek riding boots. Stick to a warm, autumnal palette—deep olive, rich cognac leather, chestnut, and classic camel. Layer up with classic pieces from Barbour, J.Crew, or Ralph Lauren. Whatever you do, leave enough room in your suitcase for tall leather riding boots (Frye or Madewell make killer pairs). --- **With these options, you're guaranteed to a perfectly fashionable fall getaway. Just remember to layer up and don't skimp on the seasonal lattes.**