First, here's a little look at what I carry day-to-day in my bag. This size of crossbody is as small as I can go for an everyday bag:
And here's how everything looks packed in:
There are two things not pictured above that I store in each of my handbags:
1. A pen. I used to carry a pen in the Ziploc bag but it would cause the bag to rip rather quickly so I just bought a bunch of pens and put one in each of my handbags instead.
2. Spare change. My pink card holder above only holds cash, credit cards, insurance cards, membership cards, etc. While I don't exactly stock my handbags with change, any time I buy something with cash and get coins back, I put it in the inside zipper compartment of the handbag of the day. Sometimes that means I have exact change handy for a purchase, other times that means I am getting 97 cents back because my handbag of the day didn't have any coins. But then next time I will have exact change! I've just found that carrying a wallet that's big enough for my coins and change means it's too big to fit in a small crossbody along with all my other stuff. So by leaving the change in each bag I free up more space.
If you're curious about what I carry in the Ziploc bag, here's a look at those items:
Bottom Row: Hand Sanitizer / Travel Toothpick / Nail Clippers / Orthodontic Wax / Burt's Bees Lip Balm / Eye Gel / Aquaphor Lotion/Lip Balm
Some of these things I carry specifically for my kids (e.g. Orthodontic Wax) and other items for myself are probably not something most people need (e.g. two kinds of eye drops). But I use all of these regularly and find it easiest to move the Ziploc bag from one handbag to another day-to-day rather than individually transferring each of these things from bag to bag or spending the money to stock every handbag with these items.
And yep, I just use a standard Ziploc zipper bag for some of my essentials. While I would love to carry these things in a nicer, cute pouch of some sort, I've tried that and it doesn't work as well as the Ziploc bag for two reasons. One, I like the bag to be see through so I can easily see and find what I need. I know there are clear cosmetic bags and I've tried those but they don't work as well because the material is too thick and structured. Which is the second reason why the Ziploc bag works for me: the material is really thin and flexible which allows it to shift around easily and fit in different spaces, and same for the items inside the bag. They can move around easily to accommodate the shape of the bag I'm using. Every couple of months the Ziploc bag starts to wear out and I have to replace it, but it's something I keep on hand in my kitchen anyway so it literally costs just a few cents.
Basically, I'm transferring just the five things pictured below (keys, Ziploc bag-o-goodies, card holder/wallet, sunglasses, phone) each time I switch handbags.
Anytime I purchase a new bag, I know it has to fit those five things or it's not going to work for me. Also, I make it a point to only purchase handbags that have one single compartment. If it has multiple compartments it's more of a hassle to transfer stuff and makes it more likely that I'll forget to transfer something out of a compartment. With one compartment, I grab everything I see (except for the pre-stocked pen) and move it to the bag of the day. The very first colored handbag I purchased has three compartments (hot pink bag at the end of the post) and I found I really dislike that since I have to put different items in different zipper compartments to make it all fit.
Choosing the Bag of the Day:
Sometimes I choose my handbag based on function for the day's activities. For example, if I'm going to a street fair with my family I'll carry a crossbody because I know I want my hands free for holding food, drinks, etc. Other days I might take my child to a doctor's appointment and opt for something bigger to bring them a snack plus their iPod and a book for me for the waiting area.
All of those items fit inside the bag with plenty of room to spare for after-visit paperwork and whatever else I manage to collect throughout the day:
Other days I can carry pretty much any size of bag I want, and I just choose based on what works with my outfit...or I'll plan my outfit around my bag. Some days I don't want to switch bags from the day prior (even though it's not that hard, it's still more effort than not changing!), other times I have a new bag I want to carry or an "old" one I feel like using again. So here's one last look at the bags I talked about in this post and how I've worn them with different outfits:
Here / Bag: Express (Similar) / Right: Outfit Post: Here / Bag: Amazon
Bottom Left: Outfit Post: Here / Bag: Amazon / Right: Outfit Post: Here / Bag: c/o Fossil
Shop the Pieces:
If you've put off getting a handbag in a fun color because of the hassle of moving your stuff from bag to bag, hopefully this gives you some possible ideas on ways to make it work for you. Of course, it's easier and cheaper just to have one bag, but there are plenty of fun, affordable handbag options out there and it really is one of those final touches to even a very simple outfit that can make it look more complete.