An airline only needs to lose your luggage once and you too will become a firm believer in carrying on.
The first time it happened to me was on a flight to Rome, where I made my connecting flight by mere seconds, but my bag did not. I spent three days in my mother's clothes, calling the airline repeatedly, terrified my bag would not arrive before we moved on to Venice. My suitcase finally made it, but since that time I avoid checking bags at all costs.
While this isn't always possible for longer voyages, if you're willing to wear your pieces more than once (excluding underwear and socks of course) and you're not one of those people who needs a minimum of five pairs for shoe selection, you can easily do this for trips seven days or less.
So here are a few of my top tips for packing light. Added bonus, you don't have to spend days uncomfortably wearing your mother's/travelling partner's generously donated, but totally not your style clothing.
First up, the bag.
Lo & Sons O.G. Travel Bag
I don't even want to admit how much time I've spent watching the cute little videos for each of their bags and drooling covetous drool on my keyboard.
Don't have three hundred dollars to drop on a bag? Yeah, me neither. Etsy and Everlane also have some good options.
Or, if you want to be all Up in the Air about it, you could also go with one on these rolly-deals from Wakamatsu.
Second, when it comes to packing, choose pieces that do double, even triple duty.
A prime example is a classic button up in a breathable fabric like cotton or silk. This one, from Madewell, would do nicely. You can wear it tucked into a high-waisted skirt, loose and casual over jeans or cutoffs, layered with a structured blazer or a cardigan: the sky's the limit.
And finally, pare it down. Instead of automatically throwing your entire makeup bag in, just bring a tinted moisturizer (preferably with an SPF of 15 or higher) blush, mascara, tinted lip balm and a cream eye liner or a nice lipstick for a night out. Do you really need 5+ pairs of shoes? Probably not. Wear your sneakers on the flight, and pack a pair of heels for a night out. Throw in a pair of flats, sandals or boots, depending on the weather, and you're good to go.
When it's all loaded into your bag, it may not look like enough, but trust me, with time and practice, you'll always have a suitable outfit, and it will never be stuck at some airport in a city where you're not.