I just saw a few nice options at Marshalls the other day. Have you tried Marshalls/ TJ Max?

I just bought a casual bag on etsy with tons of pockets and it is great. It took about 2 weeks from ordering to arriving at my door. Here is the shop:
https://www.etsy.com/shop/tippythai?ref=l2-shopheader-name

Anonymous wrote:After a recommendation on here, I just got a boken everyday bag. Can be worn on shoulder, backpack, or messanger, is waterproof and roomy. I got the slate color and it looks nice, but I wouldn't call it dressy. I love that it can convert to a backpack, though! Would have been great last year when I had to carry around multiple lunches on my oldest's K field trips.

I won't take credit for this but I've definitely recommended the boken bag on here! We have one and I love it. Agree that it is not dressy, but it's very very good, and it doesn't look like a diaper bag (more of an 'outdoorsy' bag that you might buy at REI?).

After a recommendation on here, I just got a boken everyday bag. Can be worn on shoulder, backpack, or messanger, is waterproof and roomy. I got the slate color and it looks nice, but I wouldn't call it dressy. I love that it can convert to a backpack, though! Would have been great last year when I had to carry around multiple lunches on my oldest's K field trips.

Another vote for backpack. We use a small LL bean one that's always packed with crayons/coloring/snacks/wipes/water so either parent can grab and go.
Personally, I prefer something neutral, like Timbuk2 or Manhattan Portage (probably "out" now).

you dont need a diaper bag. Get yourself a nice grownup tote bag. If you are concerned with spills, buy one on those waterproof snack/sack bags to throw in. At age 4 i usually had only an extra pair of underwear just in case and maybe a few snacks.

Try a LeSportSac bag. They have baby styles but also lots of different styles. Not sure how waterproof they are. But you can get a black one that you could dress up or down. I think they have a patent looking black bag series that might be useful. The bags are also super light so any weight will be what you are putting in- rather than the bag. Hate heavy bags.

I got a great leather backpack. Love it!

I'm more having problems reconciling "dress up" and "cross body"

I usually find lots of good work-style totes to use as our day bags.

Longchamp maybe

You can get a good quality backpack for a fraction of that $200. Like, a LLBean one in a nice pattern. I think they make the crossbody bags also, but I've never had one so I don't know capacity.

The backpacks last forever, or at least 15 years so far for mine!

Waterproof and "dress up easily" don't go hand in hand in my book...

My son is 4 and we spend many full days out & about town, no car. I've been carrying a ratty old messenger bag, but would like to get a bit closer to my old non-crappy bag self.

The two top sellers of these messenger bag: (1) it is roomy enough for a large water bottle, Planetbox, and change of kid-sized clothes (e.g., in case we stop at a splashpad), in addition to my basics of wallet, iphone, hand spray, etc. (2) it is waterproof, so I can use it year-round.

Looking to spend no more than $200 and would love something that will last at least 5 years, so more classic than trendy. And, would love something I can dress easily up or down in a cross-body style. What do you suggest?