With my Old Navy chambray shirt (similar), gold Saltwater sandals (here, here, or here), and Forever 21 leggings (similar) in a Westin Moana Surfrider elevator (they have many and the decor varies!).
Clare Vivier x & other stories crossbody shoulder bag, Tumi laptop bag, Longchamp XL Le Pliage tote, and 27″ Brics Pininfarina spinner.
I like the concept of traveling light and occasionally remind myself that I traveled around with a carryon for 2 months last summer, but in reality, sometimes I don’t want to stress about packing optimally. I loved the 21″ Bric’s Pininfarina carryon spinner (spinner puts much less stress on your wrist!) and jumped at the 27″ when it appeared on vente-privee for an extremely reasonable price. The 27″ has been checked in multiple times and has no marks whatsoever despite falling 4″ off a rack on a bus. I’m very impressed with the Italian brand’s quality — especially since I hear the worst reviews on Rimowa which costs 2-3x what I paid for my Bric’s. It looks like the model has been discontinued (the finish is a matte texture) and has been replaced with a smooth, shiny material, but you can still find both versions online for retail at Amazon, Horchow, Kaehler, Luggage Pros, Lord & Taylor, and Bloomingdale’s.
I’m a huge fan of traveling with nylon Longchamp. The bags itself are light and chic (I try to look presentable when flying). I typically use the Longchamp XL Le Pliage short handled tote as a carryall for random large objects (like shoes), duty free purchases, food purchases, or to consolidate bags as I often board with a Crumpler camera bag, the Tumi laptop bag, and purse. The camera bag does not always count towards your carryon limit. Should there be any super strict airline employees or policies (like the UK once allowing a single carryon even if you’re only transiting), I chuck everything into the Longchamp, but that hasn’t happened in ages. And if you don’t need the Longchamp, you can easily fold it up!
I used to travel with an L sized short handled tote (small travel bag) but now think it’s too small. I recommend the black or dark colors for durability, as it may pick up smudges. My black Planetes large tote is 4 years old and still going strong! While the Planetes cannot be folded up like the Le Pliage line, it is still easy to store flat in your luggage. I do not recommend the expandable travel tote unless you have an extremely strong shoulder — it’s awkward to carry when expanded. I eBayed mine — what’s the point of keeping if I can’t use it whilst expanded without injuring myself?
Longchamp is currently on sale at Bloomingdales, Nordstrom, Saks, Neiman Marcus, Magnums, Bagshop, and Longchamp (note: their inventory isn’t 100% accurate). If you’re an early bird, check Saks and Nordstrom in the morning for the best sale inventory. My favorites are the LM Metal travel bag in blue, Le Pliage small travel bag, Le Pliage large travel bag, and of course the black Planetes large tote. If you’re visiting France, I recommend making your Longchamp purses there for significant savings, but also know that you may have to visit a few Longchamp boutiques to find everything in e.g., Paris, where there is significant tourist traffic which depletes inventory.
Note on Longchamp leather: In one of my first visits to Paris, I purchased a ballet pink Veau Foulonné tote (same shape as the Le Pliage, but in leather) during the July soldes. I’m not super rough on my bags but it did not last my durability test. The corners were too delicate and showed wear after a few wears. It eventually was eBayed. For styles that require durability (e.g. big totes), I do not recommend the Longchamp leather styles. On the contrary, I have a Veau Foulonné key holder in an impractical beige color that is 6 years old and going strong…