Welcome to First Class Fridays, the weekly series you won’t want to miss!
Each Friday, I’m revealing the travel outfits that turn heads at the airport, the insider tips that make jet-setting effortless, and one small luxury that elevates your entire journey. Whether you’re planning your next escape or just dreaming of one, these Fridays are about to become your favorite. Set your reminder—First Class Fridays, every week.
Travel Outfits | Women Over 40
This week’s travel outfit is a masterclass in timeless elegance meets practical comfort. Built around the most versatile piece in any travel wardrobe—a classic trench coat—this ensemble proves that you can look polished and feel completely at ease, even on the longest journey.
SHOP THIS EDIT
The hero of this look? That belted trench coat in the perfect neutral tan. It’s the ultimate travel companion because it works as your jacket, your blanket on chilly flights, and your instant outfit elevator when you land. I’ve layered it over a navy-and-white striped sweater—classic, comfortable, and effortlessly chic. The nautical stripe adds visual interest without overwhelming the neutral palette.
The foundation is a pair of medium-wash straight-leg jeans that give you movement and breathability. These aren’t your stiff, restrictive jeans—they’re the kind that feel broken in from day one. Paired with black leather loafers featuring that signature gold horsebit detail, this outfit walks the perfect line between casual and refined. The structured black canvas tote with cognac leather handles is both practical and polished—exactly what you need for keeping your essentials organized and accessible.
Notice the gold and diamond hoop earrings? Just enough shine to catch the light without being fussy for travel. This entire outfit can take you from a 6am departure to an evening dinner reservation without missing a beat.
This travel outfit formula works because it’s built on classic pieces that never go out of style. Trench, stripes, jeans, loafers—these are the building blocks of effortless travel style. Mix and match them throughout your trip, and you’ll always look intentional and put-together.
This Week’s Insider Travel Tip: The Third-Piece Rule
Here’s the travel strategy that has saved me countless times: always travel with a “third piece” as part of your travel outfit—and that third piece should be a structured jacket or coat that can transform your entire look.
Think of it this way: you have your base layer (the striped sweater), your bottoms (jeans), and a crucial third piece that pulls everything together and handles multiple scenarios. A trench coat is the gold standard because it does everything.
Why the third piece changes everything:
Temperature control. Airports and planes are notoriously unpredictable. Gate areas can be sweltering while the plane itself is arctic. Having a lightweight but structured coat means you can regulate your comfort without looking disheveled.
The one I have traveled with for years is this one because it has a zip-out lining, making it versatile enough to wear year-round. I also own a black Burberry trench with a thicker zip outlining that I love. Sadly, many brands no longer make trench coats with this feature. Burberry used to offer it with the coat. Now they make you pay extra for it, which I find a bit ridiculous given the price point. So, I would suggest shopping at consignment stores to save some money.
Pro tip: Remove your trench to go through security in your casual sweater and jeans. Put it back on, and suddenly you’re ready for a business meeting or nice restaurant. It’s like carrying a wardrobe change without the extra luggage.
Practicality: That trench becomes your airplane blanket, your pillow when rolled up, and an extra layer of padding for your seat. I’ve used mine on countless flights, and it’s never failed me.
Versatility for your trip: Once you land, that trench works with everything in your suitcase. Throw it over a dress for dinner, wear it with different jeans for sightseeing, belt it for a more polished look, or leave it open for casual ease.
My third piece criteria:
- Neutral color that works with everything
- Quality fabric that doesn’t wrinkle easily (cotton-blend trenches are perfect)
- Functional pockets for phone, passport, or lip balm
- Light enough to tie around your waist if needed
- Structured enough to look intentional, not sloppy
The trench in today’s outfit is not one I own, but it is on sale, and the quality is good for this price point. The one I own is a bit more of a splurge, but it’s so worth it depending on your needs. It’s been photographed on cobblestone streets in Europe, worn through rainy London afternoons, and has served as my airplane companion on countless red-eyes. That’s the kind of relationship you want with your third piece.
Bonus tip: When you board, fold your trench and place it in the overhead bin on top of your carry-on. It stays wrinkle-free and is easy to grab when you need it during the flight.
This Week’s Small Luxury: Investment Loafers
This week’s small luxury is about investing in one pair of truly exceptional loafers—the kind that will serve you for a decade of travel and still look as elegant as the day you bought them.
Notice those black leather loafers with the gold horsebit hardware in today’s outfit? That’s not just a shoe choice—it’s a travel strategy. A pair of classic, well-made loafers is one of the smartest investments you can make for your travel wardrobe.
Why investment loafers are worth every penny:
Timeless versatility: Black leather loafers work with literally everything—jeans, trousers, dresses, skirts. They’re your Swiss Army knife of footwear.
Airport ease: Quality loafers slip on and off effortlessly for security. No laces, no buckles, no fuss. Just easy, elegant efficiency.
Comfort that lasts: Well-constructed loafers with quality leather actually get more comfortable over time. The leather molds to your foot, creating a custom fit. Cheap loafers never achieve this.
Destination-ready: From the airplane to the art museum to dinner, investment loafers carry you through your entire trip without ever looking out of place.
The details matter: That horsebit hardware? It’s the difference between “nice shoes” and “those are GREAT shoes.” Small luxury details elevate your entire look without being loud about it.
Where to invest: Look for loafers in supple, quality leather (not bonded or corrected grain). The sole should be leather or high-quality rubber with good traction. The hardware—whether it’s a horsebit, tassel, or simple trim—should feel substantial, not flimsy.
Classic black is the most versatile, but don’t overlook cognac brown or deep burgundy if those work better with your wardrobe. The key is choosing a color you’ll wear repeatedly, because these loafers should become your default travel shoe.
I have two pairs of Gucci loafers, one purchased in 2005 and the second purchased in 2021. They stand the test of time. The ones I wear most are the Gucci Jordaan. If you prefer a more affordable pair, these Quince Horsebit loafers are fabulous. It comes down to where and how you want to invest in your closet. For me, these are one of my most-worn shoes, so they are worth the splurge. I’ve worn variations of this style through dozens of airports, and I always notice how they change the way an outfit feels. Suddenly, your casual jeans and sweater look more intentional, more curated, more “I know exactly what I’m doing.”
Pro tip: Before your first trip with new investment loafers, wear them around the house for a few days with the same socks you’ll travel in. This breaks them in just enough to prevent any rubbing without sacrificing that crisp, new look. And always pack a small leather conditioning wipe in your toiletry bag—a quick shine in the hotel bathroom before dinner makes them look brand new again.
What’s your third piece go-to? Have you found your investment loafers yet? Drop a comment below—I love hearing what works for you!
First Class Fridays
That’s it for this week’s First Class Fridays! Try the third piece rule on your next trip, recreate this classic trench-and-stripes formula, and consider investing in those loafers you’ve been eyeing. See you next Friday for another dose of elevated travel inspiration. Until then, happy travels!
In case you missed my previous First Class Fridays posts:
