Maybe it would be fun and helpful for you if you posted links to the sort of outfits you like and we could all show you what bags we’d pick to go with it. I’m not sure if you just aren’t sure of your ability to pick something that goes well or if you don’t have a defined taste and tend to pick things out that either don’t work for you or which you decide aren’t the right look for you after you’ve spent your money. Am I overthinking this??
I have pretty defined tastes but they vary because my style varies from polished looking and tailored to bohemian and casual.
Black is always good and matches just about everything but pale summer dresses and resort wear. I even like pastel with black but overall, black just seems too serious for the summertime outside of work and evening. For summer my favorite neutral is saddle leather. It goes with everything so you don’t have to constantly change your bag, because I, like others here mention, always seem to leave something out by mistake!
Nowadays there are so many pretty colors to choose from. Color can be a fun change and it perks up an outfit like jewelry does. I never pay more than $100 for a bag and often a lot less so if I see a color that will go with a lot of the colors I wear or just look really good worn with black I indulge myself. I have to admit that a lot of times because I hate the hassle of changing all my stuff into a new bag I tend not to use these frivolous colors as much as I think I will when I buy them.
But I do so love this purple bag and this orange tote bag.
As for size, I like medium to large. I like the top to open up wide so I don’t have to grope around blindly to see what I’m trying to find in the bag. It’s also a nice feature, but not essential, to have the string with the clip on the end to pull your keys out.
Leather is more durable than most vinyls so I generally buy leather. If I do buy vinyl it usually has a texture to it like snakeskin or crocodile. I hate the type of vinyl that feels rubbery and makes squeaky noises! Argghhh!!! Hate it!
I like an inside pocket for change and one for my mirror, comb and cosmetics.
A shoulder strap is critical for me or handles large enough to comfortably put on my shoulder. I commute and I’m always carrying a lot of stuff with me so I need something I can sling over my shoulder to leave my hands free.
I like to have a zipper or secure closure vs. an open topped bag to prevent theft.
Outside pockets are nice for cell phone and transit passes.
Stylewise I have certain features that I am always drawn to:
Topstitching detail
Interesting Hardware
Pretty lining fabric
Outside Pockets
Buckles and straps
There are practical considerations and style preferences. If you can find a bag that fulfills both it is a keeper!
mangeons I like your bag too! It is a bookbag style. I once met a boyfriend because I was carrying such a bag. He joked with me saying “I like your bookbag, do you have a lunch box that goes with it?”