I don't own any Parker's so I can't compare, but they do seem to be a bit underrepresented here in the clubhouse. I actually prefer shoulder bags and it's how I wear my Cassie if I'm not clutching it or carrying it in a larger tote. They are cute, compact, and very easy on the eyes, I also think it's about as close as Coach has gotten in recent years to a true unisex bag, although that's not an issue for me personally, I wear what I like.
Other attributes with the Cassie: it's versatile, lightweight, and can hold up better in the damp pacific northwest climate than bags that are more delicate. The handle was the big sell for me, you can slide your hand through and have extra security when carrying as a clutch. This feature is common with many of the inexpensive European and Asian bags I see on Amazon that are marketed to men and I used to own a few before I got into designer bags.
The strap is decent, I've had my share of strap related problems over the years but this is a keeper for me, the color-block aspect is a big plus. I also feel it's appropriate to the size of the bag, and Coach, like a lot of designers, have struck out on many of their strap choices, probably to get people to buy additional $200+ straps.
The interior design of the bag is perfect for those of us that like structure. Case in point: last night while out I spent five minutes digging around the darn tote I was wearing in order to find a small bottle of eye-drops. Ugh! I'm sure we've all been there and I was cursing myself for not taking my Cassie. While many describe the Cassie as a small to medium bag, it's probably not going to work with people that carry large bulky north/south items. It works for me because I stick to flat east/west items that can be placed sideways; there's some slight tapering but nowhere near as severe of a narrowing as other bags.
A typical day allows me to carry:
-keys (house and car)
-medication
-deck of cards (for Starbucks)
-earbuds
-small inexpensive pouch I use as a wallet
-phone
-spare set of keys
-energy bar
-mints
-travel size bottle of tums
Day-trips: I might add a charging cable and spare battery
For carry-on: One of the thinner pockets can hold tickets/itinerary if folded in half
And I still have plenty of room left over, I have not yet come even close to filling this bag, I've seen a few people on YouTube that have packed their Cassie's so tight I can hear them screaming but the bags have some decent pliability for short term situations at least.
I think the main caveat is the size. The only people that seem to have trouble adapting to them are those that like to carry A LOT of stuff. My own Mom included, she finally bought one after some serious selling of the bag on my part all summer. But she's a carryall gal, and has had issues with using it as her daily, so it'll probably be for special occasions only.
I suggest going to a boutique or Macy's if able and trying one on, or ordering one online and just return it if it doesn't work.
