Goodbye, Oscar — And Hello to My Next Travel Sidekick – Finding the Best Carry-On Suitcase with Features that Fit

After more than 20 years of loyal service, my Samsonite carry-on — lovingly dubbed Oscar — is finally headed into retirement. He’s been by my side on countless adventures, but lately, the cracks are showing (literally). As I prep for my next chapter of travel, I’m not just replacing old luggage — I’m looking for the best carry-on suitcase features to match how I travel now: smart, efficient, and carry-on only. This post isn’t just a goodbye—it’s a packing strategist’s blueprint for what comes next.

Goodbye Oscar, …Hello Luggage Upgrade

I’ve never been one to chase trends or replace things just because something shinier comes along. My Samsonite carry-on — lovingly named “Oscar” — has been with me for over two decades. Together, we’ve seen Caribbean breezes, backroad Southern towns, delayed flights, and dreamy weekends that turned into stories.

But after my recent 3-day Kentucky getaway, I realized: Oscar’s time has come. His zippers are temperamental, his wheels wobble, and his corners have taken one too many hits on airport ramps. He’s earned his rest — and I’m officially suitcase shopping, and sadly replacing my old luggage.

Why the Right Carry-On Matters

When you travel often — especially carry-on only — your luggage isn’t just gear. It’s your mobile command center. Your co-pilot. Your calm in a chaotic terminal.

The right carry-on makes travel easier. The wrong one? Adds stress, delays, and broken wheels right before boarding. And as The Packing Strategist, I don’t just choose a suitcase. I curate a travel tool that fits my rhythm, style, and efficiency.

What I’m Looking for in My Next Carry-On

Here’s my non-negotiable wish list as I hunt for the perfect upgrade:

• Durable, lightweight shell – Tough enough to protect, light enough to lift solo.
• Smooth 360° spinner wheels – Zero resistance gliding through terminals is a must.
• Expandable capacity – Room for last-minute finds or layers on chilly flights.
• Smart interior layout – Think: compression straps, dividers, and cube-friendly spaces.
• TSA-approved lock – Built-in security without extra hassle.
• Side handle – Because those overhead bins don’t load themselves.
• Neutral, timeless design – Understated. Elegant. Always travel-ready.

Bonus Features I’d Love

These aren’t essential — but if my next bag has them, even better:

• USB charging port for long layovers or delays.
• Exterior pocket for laptop or grab-and-go travel docs.
• Matching weekender or tote for those short hops.

Brands on My Radar

Right now, I’m narrowing it down to a few standout contenders:

• Away luggage – Sleek and minimalist with built-in tech features.
• Monos luggage – Stylish and ultra-durable with great interior organization.
• Briggs & Riley – Known for lifetime guarantees and business-travel durability.
• Samsonite – The OG. After all, Oscar held up for 20+ years.
• Delsey – has the Ultra-Secure Securitech® 2 Zipper that is 3x more resistant than most luggage zippers
• Level8 – has the ultra quiet 360° Spinner Wheels

And if you’re a luggage brand reading this… yes, my DMs and inbox are open. I’m hunting for my next packing soulmate.

When Will I Make the Switch?

I haven’t pulled the trigger yet. I want to test a few options, do side-by-side comparisons, and share my real-world results with you. Whether it’s a few weeks or a month from now, I’ll be taking you behind the scenes through the entire process.

FAQ — Upgrading Your Carry-On

• What size carry-on is best for most airlines?
  • A 21–22 inch carry-on typically fits within domestic and international airline regulations. Always double-check before your trip.

• Is hard shell or soft shell better?
  • Hard shells offer more protection and style, while soft shells provide flexibility and more exterior pockets.

• Are built-in locks worth it?
  • Yes — if they’re TSA-approved. They keep your belongings safe without extra accessories.

Final Thoughts from The Packing Strategist

Replacing a suitcase might seem like a small decision — but after 20 years, it feels like a milestone. And for anyone choosing their next carry-on, remember: this isn’t about the brand. It’s about how that bag fits your travel life.

I’ll be testing options, doing live walkthroughs, and reporting back right here. So stay tuned — Oscar’s successor is coming soon.

Finding the best carry-on suitcase isn’t about chasing trends or spending the most — it’s about choosing something that truly fits your travel style, your body, and your life. Whether you’re rolling through the airport for a quick weekend escape or living out of your bag for two weeks abroad, the right features make all the difference. I hope this guide helped you feel more confident in your next suitcase decision — and maybe gave you permission to say goodbye to your own “Oscar,” too.

Finding the best carry-on suitcase isn’t about chasing trends or spending the most — it’s about choosing something that truly fits your travel style, your body, and your life. Whether you’re rolling through the airport for a quick weekend escape or living out of your bag for two weeks abroad, the right features make all the difference. I hope this guide helped you feel more confident in your next suitcase decision — and maybe gave you permission to say goodbye to your own “Oscar,” too.

Mini Confidence Packing Guide For Travelers

• Travel with confidence means:
  • Packing light enough to move freely.
  • Choosing luggage that works as hard as you do.
  • Trusting that you don’t need to bring everything — just the essentials.
  • Upgrading when it’s time, without guilt over retiring the old.
  • Remembering: the right bag is not just luggage, it’s freedom in motion.

Related Posts You’ll Love

• Packing for Two Weeks in a Carry-On: My Proven System for Stress-Free Travel
• My 3-Day Kentucky Packing List: What I Fit in My 20-Year-Old Carry-On
• What’s In My TSA-Approved Toiletry Bag?