Inspiration - H&M
I have owned the same random Target laptop bag since the very beginning of college. (13 years - eep.) It is black and basic and well past it's expiration date. It has traveled the world with me, often carrying two laptops at a time, and after years of abuse it was really showing it's age.
Right before I went to DC for work in July I started thinking about how I was spending time, money & effort on my wardrobe to look polished & professional and yet I was lugging the Pig-pen (dirty kid from Peanuts comic) version of a laptop bag around. It had gotten so beat up & worn out that it was detracting from my overall business appropriate impression. (In my head I imagined clients thinking, "Why did this competent & professional project manager go dumpster diving for her laptop bag?") It was well past it's time to be replaced.
I decided to look into an investment priced bag considering I carried the last one for so long and when I travel (frequently) it's glued to my side the whole trip. My fashionable & great-at-deal-finding friend mentioned that if you keep an eye on Kate Spade laptop bags they go on decent sale a few times a year and when I checked Amazon I was lucky it happened to be one of those times! I bought the Kate Spade Calista laptop bag for half-off full price. Score! (Sadly, it's not on sale anymore.) And I love it. It's super lightweight, has a decent number of pockets and the inner lining is a polka-dot pattern. Too cute.
If you're interested - below are links to a few examples of handbag-like laptop bags that I think are both professional and cute. It took a little searching to find filter out the boring, utility-only ones but I think I found some good options at various price points.