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 all about sophisticated but relaxed style. These travel outfit formulas are easy to recreate with wardrobe essentials you likely already own. Now that Fall has arrived, layering pieces will be your best friend. Here I have paired a relaxed, white button-down shirt with a lightweight cashmere sweater. If you get warm, you can easily remove your sweater and drape it over your shoulders or trench coat. Don’t miss my latest 23-piece travel capsule for those must-have travel outfits that will leave you feeling sophisticated and chic, but equally comfortable.
SHOP THE LOOK
This Week’s Insider Travel Tip: The 24-Hour Rule for Effortless Style
Here’s the travel hack that changed everything for me: lay out your travel outfit—including jewelry, shoes, and bag—24 hours before you leave. Not the night before. A full day before. I promise that this makes all the difference.
Why? Because this is when you’ll realize your favorite loafers need polishing, your trench coat needs a quick steam, or that white shirt has a tiny stain you didn’t notice. It’s also when you’ll have that moment of clarity about whether this travel outfit actually works for a long flight or if you need to make any adjustments. There is nothing worse than feeling uncomfortable on a flight – especially a long flight! Your travel outfit is one of the most important outfits you will pack for your trip. This is the one that has to do double duty- it’s not just for sightseeing, walking around, or dining; it’s the one that has to hold up on the plane.
Hang everything together in one spot where you can see the complete look. Take a photo with your phone. Walk away. Come back an hour later with fresh eyes. This is when you’ll spot what’s not working—maybe the jeans are too stiff for long-haul comfort, or you need a different bag that fits your laptop.
The 24-hour rule removes all travel day stress. No frantic ironing at 5am. No discovering shoe scuffs as your Uber arrives. No “I have nothing to wear” panic that makes you grab the wrong thing. You board that plane calm, polished, and ready—which is exactly how elevated travel should feel.
Bonus tip: Use this time to pre-pack your personal item too. Nothing kills that first-class energy faster than digging through your bag for lip balm at 30,000 feet.
This Week’s Small Luxury: A Monogrammed Travel Essential
Let’s talk about the power of a monogram. Not just any monogram—one on something you’ll use every single trip. This week’s small luxury is investing in a beautifully monogrammed travel piece, whether it’s the canvas tote like the one featured in today’s outfit, a leather passport holder, or even a cashmere travel wrap.
There’s something deeply satisfying about pulling out a personalized item at the airport. It’s not about flash—it’s about that quiet confidence that comes from knowing your things are distinctly yours. No more wondering if that’s your black bag on the carousel. No more generic travel gear that could belong to anyone.
Where to Invest?
Look for classic pieces in neutral colors that will work with everything in your wardrobe. Canvas totes with leather trim, leather luggage tags, or linen pouches for organizing your carry-on. The monogram turns a simple item into an heirloom—something that ages beautifully and travels with you for years. Here are some of my top picks:
- Canvas weekender tote (like today’s featured bag): Perfect for tucking under the seat, holds everything you need in-flight, and looks polished in the overhead bin chaos
- Leather passport holder: Every time you hand it to customs, you’ll feel that little spark of luxury
- Cashmere travel wrap: Monogram it subtly on the corner, and suddenly your airplane blanket situation is solved forever.
The best part? These make incredible gifts for yourself (yes, you deserve it) or for the fellow travel lover in your life. Start with one piece, and watch how it elevates every journey.
Pro tip: Choose a monogram style that feels timeless. Classic block letters or elegant script in neutral thread colors (navy, cognac, or cream) will never go out of style.
What’s your favorite travel outfit formula? Drop a comment below—I love hearing what works for you.
First Class Fridays
That’s it for this week’s First Class Fridays! Save this outfit formula, try the 24-hour rule on your next trip, and treat yourself to that monogrammed piece you’ve been eyeing. See you next Friday for another dose of First Class Fridays and elevated travel inspiration. Until then, happy travels!
In case you missed my previous posts, you can check them out here:
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