1st, there is no such thing as a "maximum legal carry-on" (I just wrote it for Google's sake). Stylish: - Tumi (but it does not offer a lifetime warranty and experience with customer service is mixed) - Filson, Chapman Bags UK (more classic, lifetime warranty) Functional: Just read this - http://www.onebag.com/bags.html this - http://www.onebag.com/business-bags.html this - http://www.onebag.com/leisure-bags.html and this - http://www.onebag.com/dual-purpose-bags.html Truly functional offerings but how stylish it is? Especially thinking of the business bag. How To Pack It? Including: Click on graphics to enlarge it! Not functional: - Wheels - Hard case (See above) Conclusion? Is style and function (according to the above) already coexist in a readily available consumer product? Edit: obviously only soft sided bags are acceptable with regards to airline policies; you can fit the bag in the cage if it is not 110% loaded.