1. How do you decide what bag to carry each day?
Often the bag tends to be the last decision I make, to add a little something to the outfit. However, my outfit will sometimes be influenced by the day's agenda. Like, if I know I'm going to need to stuff scarf/cardigan/water bottle/umbrella in my bag.
That said, I do often go on "jags" and carry the same bag every day for a week on end, and challenge myself to build outfits around it. I have been doing that lately with my cobalt bag.
2. Should a bag match or contrast with an outfit?
I prefer contrast, which is probably why I have so many white or cream bags. That said, my cobalt bag jag lately has me doing a lot of tone-on-tone.
3. What's a casual vs. dressy bag?
For me, a casual bag is slouchy, whereas a dressy bag is more structured. In fact, I have been on the cobalt jag because I've been dressing more casually this week. I would like to add another casual, slouchy bag to my collection but haven't found the right one yet.
4. Does size matter (HA!)?
Absolutely! This is my number one bag frustration: finding one that is proportioned just so, for my 5' frame. I do like the oversized bag look, but what is oversized for regular sized people is ENORMOUS on me. This is true when it comes to clutches as well. I'd probably own a lot more purses if they made them in "petite" options.
Other thoughts:
a. I do not like heavy purses. Makes me tired to lug around a heavy purse. I don't like shopping online because I can't feel the weight of a bag. There are some really heavy purses out there.
b. I do not like a hardware that goes clang and ka-ching ching. I do like the look of a chain purse but that would just drive me NUTS.
c. FEEL of a bag is very important to me.. and on this, I've slowly gravitated towards higher end prices ($300-500 range). I will still buy what I call "fun" bags in lower price ranges, but I prefer real leather. I love a luxurious linings. I love a quality zipper. And for this reason, unless I'm familiar with the brand, I just can't shop online. I need to touch and pet the bag.
d. Consider hardware when making your decision. The most versatile is bronze or pewter rather than silver or gold. Or if you wear more of one metal than the other, stick with that. Or, look for purses that have very little obvious blingy hardware, so it doesn't matter so much if you mix-and-match your metals. (I know lots of people mix-and-match, but this always bugs me for some reason).
e. Carry-ability is important! Again, this is hard to determine when shopping online. I can't stand it when straps won't stay on my shoulder. How long is the strap and does it hit just right, so that the bag rests nicely at your side, rather than banging at your hip, or too close under the armpit? If it's a clutch... I insist on having a wrist strap. This comes in handy when you are going to the restroom, trust me. Do you like cross-body straps? I don't. I never use the optional ones either. If the bag is meant to be held in your hand, or looped across your forearm, not on your shoulder, is it comfortable to carry that way? These are things you need to test drive!
f. I'm not as picky about pockets and places to organize items within the bag. Although it's nice to have an interior pocket big enough for hygiene products. And I do like purses that have a pocket that is good for tucking in a cell phone so it's easy to find.
g. If you're going with black for a purse, it's like shoes: find something interesting. No flat black pebbled leather -- boring. Crackled patent is awesome. Or other detailing.
h. Look for metal feet on the bottom. This will keep your purse clean. No matter what you may imagine, there's always that occasion when you may have to set it on the ground. Yuck.
i. Color: I think it's kind of like shoes... everyone has a standard "neutral" that works. For me, it's cream. For you, it very well may be black or a rich deep brown, to go with your hair.
j. Everyone must have a red bag -- it has to be "your" red. It took me forever to find my perfect red bag, in my preferred shade of red.
k. Lately I've been matching bag and shoes a lot. I haven't done that in forever, but suddenly it seems fun to me.
l. If you buy a clutch, make sure it fits everything you want to carry in it. I had to release a bunch of clutches recently that do not fit my cell phone or wallet. I used to take money and cards out of it, and put it into the clutch. Too much hassle. There are a lot of cute clutches out there that aren't large enough even for my phone.