Checking a bag is a tax on your time. Baggage fees, waiting at carousels, lost luggage risk, and the mental overhead of a bag that might not arrive when you do. Everything below fits in a standard carry-on (22x14x9") with room to spare, and none of it involves packing so light you feel like you're sacrificing.
The Away Carry-On is the benchmark for a reason: hard shell, TSA-approved lock, compression packing, ejectable battery for in-airport charging, quiet wheels. It's expensive for a suitcase but the build quality means you buy it once. The medium size (21.7") fits in every overhead bin I've ever encountered, including smaller regional jets.
Packing cubes compress your clothes and let you find things without unpacking everything. The Eagle Creek Pack-It Specter set is the lightest available. Use one cube per category: shirts in one, bottoms in another, underwear/socks in the smallest. Everything stays organized even after a week of opening and closing.
Most carriers allow a personal item in addition to a carry-on — this is where the real carry-on-only magic happens. A well-packed backpack or tote holds your electronics, toiletries bag, reading material, snacks, and anything you need during the flight. The Aer Day Pack 2 or the Bellroy Transit Backpack are both designed specifically for this use case.
3-1-1 rule: containers must be 3.4oz or less, all fit in a 1-quart zip bag, 1 bag per person. Get actual travel-size containers (leak-proof) and transfer your products. The Umite Chef Travel Bottles set has consistently been the most reliable under $10. Airlines confiscate a lot of liquid — transfer everything before you go through security, not at the airport.