2025
“Twenty-five years ago, a show called Gilmore Girls premiered, and apparently, took the season of fall hostage.” Lauren Graham at the 77th Emmy Awards, reuniting with her on-screen daughter twenty-five years later.
Fall Vibes
Today is the first day of fall. Fall is my favorite season. What’s not to love? The cooler temperatures, seasonal food and beverages, the leaves changing colors, and, of course, the best fashion. It’s sweater weather!
Time to bust out the jeans, sweaters, blazers, jackets, loafers, sneakers, and scarves while you sip on your favorite fall beverage. This post will cover some ways you can embrace fall vibes and dress in fall trends.
A Gilmore Girls Fall
We have officially entered Gilmore Girls season. What does a series from the early 2000s have to do with the fall?
There are a lot of reasons people associate Gilmore Girls with fall. The mother-daughter duo lived in a small New England town with an abundance of fall activities; they wore the best fall trends and drank hot beverages all year.
From Brit + Co: The One Reason ‘Gilmore Girls’ Is A Fall Show, According To Amy Sherman-Palladino
Gilmore Girls creator, Amy Sherman-Palladino told The Hollywood Reporter exactly why the show is so incredibly fall-coded. Sherman-Palladino told The Hollywood Reporter that she and her husband (co-creator Dan Sherman-Palladino) decided to take a fall trip to Connecticut right after Gilmore Girls finally sold. “We encountered that small-town feel, that feel of hayrides and pumpkin patches and hot apple cider. It almost felt ridiculous — the jaded woman that I am, I was like ‘This is like central casting laid this out for us. People don’t live like this,’” she said. “But they do in some places, and that creatively fed me the rest of the show. Most of the show is about Lorelai [Graham] creating this world that she and her daughter [Bledel] can both grow up in together.”
Now is the time of year to watch, or rewatch, Gilmore Girls. I started watching the series for the first time last fall.
Fall Activities
From Everygirl: Grab Some Coffee and a Takeout Menu: 12 Ways to Have a Gilmore Girls Fall
2. Get back into reading. “Rory famously brings a book with her wherever she goes, but if it’s been a while since you last cracked open a book, fall is the perfect time to get back into it. Head to your local bookstore or library and pick out a new release that has you excited or something cozy you can curl up with. For peak Gilmore Girls nostalgia, try tackling Rory’s actual reading list from the show and see how far you get. It might take you a while to get through all 500+ books mentioned in the series, but you’ll have plenty of material on your TBR list all season long.“
4. Take a spontaneous road trip. “A spur-of-the-moment road trip is peak Lorelai energy and the perfect thing to add to your fall bucket list. No pro/con list necessary—just hop in the car (with a coffee in hand, of course) and drive until you stumble upon something fun. Stop off at a roadside diner, find a small town with great shopping, or just enjoy the scenery along the way. You could even make it an overnight trip and check into a cute bed-and-breakfast.“
9. Tailgate for a football game “One of my all-time favorite episodes is the one where the whole Gilmore clan tailgates for the Yale vs. Harvard game. Rory in her chunky turtleneck sweater, Emily and Richard decked out in full Yale regalia, Lorelai causing drama by calling Pennilyn Lott her “almost mommy”—it’s peak Gilmore Girls if you ask me. And as this episode proves, you don’t have to be a football fan to have fun tailgating. Head to your alma mater (or a local college stadium) dressed in your sportiest gear and grill with friends before the game.“
10. Go antiquing. “Kim’s Antiques is an iconic location in the show, and I personally would love wandering around the overstuffed rooms and haggling with Mrs. Kim. Whether or not you live in a small New England town, there are bound to be some antique shops near you, and I can’t think of a better fall weekend activity. Embrace your inner Emily Gilmore, don a matching set and some sneakers, and go hunting for some treasures to bring home.“
12. Find a local festival near you. “One thing about Lorelai and Rory? They never miss a town event. From the Bid-on-a-Basket fundraiser in early spring to the Autumn Festival to the snowman-building contest, Stars Hollow has no shortage of seasonal festivities, and the Gilmore girls are enthusiastic participants in all of them. Even if your town doesn’t share Stars Hollow-level excitement for every holiday, there are bound to be some local events or festivals happening around you this fall. Whether it’s a simple farmers market or a full-on fall festival, find something fun and festive to do in your community this season.”
Find a local festival/event: Fall fun in Boston
7. Perfect your coffee order. “We can’t all guzzle black coffee at all hours of the day and night like the Gilmores can. If your taste in coffee is a little more refined, but you haven’t yet found your ideal coffee order, make it your mission this fall to find your perfect cup of coffee. Whether you’re ordering at a coffee shop or making a cup at home, experiment with different coffee roasts, syrups, creamers, and other mix-ins to create your perfect cup.”
Order your favorite fall beverage. It’s pumpkin spice and apple cider season.
Plan a fall trip. If the above activities don’t appeal to you, plan your own adventure. Here are some articles about where to spot the best fall foliage.
From AFAR: This Fall Foliage Prediction Map Will Help You Plan the Perfect Autumn Getaway Across the U.S.
From Travel & Leisure:
These 25 U.S. States Will Have a ‘Spectacular’ Fall Foliage Season, According to AccuWeather
7 Picturesque U.S. Small Towns to Visit for a Memorable Fall Getaway
This East Coast Destination Is an Autumn Lover’s Dream—With Apple Orchards, Elegant Inns, and Forest Hikes. I stayed in Litchfield this summer, and it reminded me of Gilmore Girls.
Fall Trends
I have been reading about fall trends for a few weeks now. I’ve created a list of trends and essentials on repeat in the articles I’ve read. I’m including all the links, along with my notes.
For men:
From GQ: The Biggest Men’s Fashion Trends 2025 Has in Store, According to GQ Staffers
For women:
From PureWow: Sardine Girl Summer Is Over—Welcome to Fisherman Core Fall
From Vogue: How to Dress Like the Olsen Twins This Fall
Make it a Preppy Fall
Fall + Preppy clothes = perfect match
As you can see, I still have my copy of The Preppy Handbook, purchased in the ’80s. Some preppy styles are always in trend, including the polo shirt, loafers, cable-knit sweaters, and tennis sneakers. This year is no exception.
From Who What Wear: Polos! Satin Scarves! Cable-Knits! Preppy Style Is Back for Fall and It’s Here: The It-Girl Sweater Trend of Fall 2025
From Rank & Style: Now Trending: Polo & Rugby Shirts
From Marie Claire: Katie Holmes’s Boat Shoes Add a Preppy Twist to Fall’s Silk Skirt Trend
Loafers
I consider loafers an essential part of my fall wardrobe. They are comfortable and stylish.
For women:
From Real Simple: Reviewers Walk Comfortably for Up to 17,000 Steps a Day in These Podiatrist-Approved Loafers—and They’re on Sale
From Rank & Style: Trending Loafers
From Who What Wear: Loafers Are My Go-To in Autumn—5 Classy Trouser Styles That Pair Best With Them
From Vogue:
Vogue’s Definitive Guide to the Best Loafers to Invest In
The Latest Loafer Trend Is a Triple Threat—Sleek, Stylish, and Sophisticated
For Men:
From GQ: The Best Loafers for Men Are the Most Crucial Shoes of 2025
From CNN: 16 best men’s loafers to add to your wardrobe this fall, according to stylists
Socks
Add a pair of socks to your outfit:
From Marie Claire: My Perfect Transitional Piece? A Pair of Great Socks
From GQ: Why Is Everyone You Know Wearing White Socks and Loafers?
Fall Essentials
The fall essentials list is a long one. Here are some items you can use to create a capsule wardrobe.
For women:
From Marie Claire: I’m Obsessed With Fall Shopping—10 Pieces I’m Craving This Season
From Bazaar: The 22 Key Pieces Every Fall Wardrobe Needs
From Elle: How to Build the Perfect Fall Capsule Wardrobe With Just 15 Items
Denim
Denim is a trend in the fall as evident as florals are in the spring. But, trending denim styles are constantly changing. You might find it exhausting and frustrating to keep up with the changes. My rule when shopping trends: I have to love it to buy it, because I will wear it after it is considered out.
2025 denim trends for men and women include: straight-leg, wide-leg and flared, embellished denim, denim on denim, and dirty denim.
From Marie Claire: These 6 Fall 2025 Denim Trends Already Earned the It-Girl Co-Sign
Keep scrolling to take a closer look at the denim trending this fall, ranging from slim and skinny to super-sized, baggy jeans. Plus, tips and insight into how to style each jean this season.
From Elle: These Denim Trends Will Change How You Dress This Fall
From Who What Wear: This Just In: The Denim Wash That’s About to Dominate Every Cool Outfit This Fall
Denim on denim and denim accessories:
From PureWow: The 3 Rules of Wearing a Jean Jacket in 2025
From Elle: The Denim Accessories Poised to Dominate Fall Street Style
From Vogue: Double or Nothing! 7 Ways to Wear Denim on Denim
For Men:
From Men’s Health: The 16 Best Jeans for Men, Tested and Reviewed by Style Editors.
Our Men’s Health team did the legwork (literally)—even the guys with beefy quads—finding cuts that work for coffee runs to date night without feeling stuffy or too casual. Think of them as the anchor of your wardrobe, grounding every fit to make you the coolest guy at every occasion. Whether you want something that stretches with each stride, breaks in beautifully over time, or just looks clean every day, these are the 16 best jeans for men to shop right now.
From Esquire: 4 Denim Trends to Know (and Wear) in 2025
From Wirecutter: The Best Men’s Jeans
Sneakers
For women:
From Rank & Style: Top 10 Dress Sneakers For Women
From Elle: Fall’s Most-Wanted Sneakers, According to Editors
From Bazaar: 14 Fall Sneakers to Kickstart Your Seasonal Shopping
From Vogue: 10 Sneaker Trends to Have on Your Radar This Fall
For men:
From Esquire:
The 10 Best White Sneakers of 2025
The 8 Best Sneakers You Should Buy for Fall 2025
Boots
For men:
From Wirecutter: The best men’s fall boots, according to stylists and podiatrists
For women:
From Elle: Your Style Guide to Fall’s Boldest and Chicest Boot Trends
From Rank & Style: Tall Boots
From PureWow: From Ankle to Knee-High, DSW Has the *Best* Fall Boot Selection (and Your Wallet Would Agree)
From Who What Wear: Here They Are: The 6 Biggest Boot Trends of Fall 2025
Clogs
For men (and women): These cult-favorite sustainable clogs just restocked and you could save $20 with this promo code
From InStyle: Are the Divisive Birkenstock Naples Clogs Already Becoming Fall 2025’s ‘It’ Shoe?
Jackets
What jackets do you associate with the fall? If you guessed trench coats, barn jackets, suede, blazers, and moto jackets, you would be right.
From Rank & Style: Trending Jackets
From Elle: The Cropped Trench Coat Is Fall’s Defining Outerwear, and We Found the Best Ones
Plaid
Plaid, like denim, never goes out of style in the fall.
From Marie Claire: Trust Me: You’ve Never Seen Plaid Like Fall ’25’s Take on the Classic Checked Print
To no surprise, plaid is poised to rise in popularity this fall (once again). The timeless pattern is a quintessential autumn print, often emerging in the form of flannel shirts and checkered coats when temperatures plummet below fifty degrees.
From Who What Wear: Hang On—Is This Clashing Styling Trick Fall’s Next Big Trend?
From Purewow: 5 Ways to Wear Plaid Like a Fashion Editor in 2025 (Plus One Popular Look to Skip)
Top Trends for Women
More top trends: Lace, animal prints, ballet flats. Read more:
From Birdie: Move Over, Minimalism—Fall’s Top Jewelry Trends Are About Quirky Decadence
From Elle: The 7 Street Style Trends Fashion Insiders Backed This Season at New York Fashion Week
From purewow: I’m a Fashion Editor. Here Are the 20 Items I’m Most Excited to Buy This Fall
From Who What Wear: Here You Go: 5 Trend-Forward Fall Outfit Ideas I Think Are Wildly Chic
From PureWow: These 9 Fashion Trends Will Rule Fall 2025 (Plus One I’m Ready to Retire)
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