The Handbag Dilemma

I've been carrying the same handbag since my freshmen year of college: a Kate Spade Wellesley Alessa black leather crossbody bag. While this might not seem like the most impressive feat, I used to cycle between three or four handbags a year. Granted, they were all cheaper and from either Target or Urban Outfitters, but I didn't know how to stick to a handbag. I decided after a long summer of working in the weeks before I started college that I wanted to buy myself my first designer handbag. I am a massive Kate Spade fan and have always ogled over the handbags in the outlet for months upon months. It was a gorgeous August afternoon when I finally walked out of that store toting one of the large, white shopping bags full of the purse of my dreams.

For my first designer bag, I wanted something that I would wear and wear and wear with no issues. I picked a crossbody big enough to hold a book, magazine and notebook if needed. Really, I just tried to pick out a classic shape in a staple color. Hence, my favorite black crossbody bag.

I think by now the outcome of this post is obvious...I'm starting to get bored of my bag. I still love it, like a lot. But sometimes it's just too big and too boxy for me. I've been itching for a new handbag and it's been quite the dilemma. I'm not ready to get one yet, but I think that it'd be a nice graduation or early graduation present to myself.

I want to do research before I dive headfirst into a new handbag. It'd be an investment, as far as I'm concerned. There are some questions I've been cycling through to narrow down what I might be looking for and how I want to go about having it.

1. Do I want brand new or pre-owned? There are so many different places online, reputable places at that, who sell pre-owned designer bags at incredible prices. You have to sift through a lot of styles, but it becomes sort of a game to find the perfect match. We get a lot of handbags at work, so I get the urge quite frequently to drain my bank account. However, from this, I have also learned to be incredibly picky.

2. How do I bridge the gap between too trendy or too classic? I'm not in any financial position to be purchasing "it" bags and getting sick of them months later when I regret everything about my purchase. On the other hand, I don't want to get something that's too classic and get sick of it because I find it too boring or too simple. I already have a simple, classic bag. I don't need two of them, right?

3. What size do I want to get? Normally I have to have my bags pass the magazine test. If I can't fit a magazine into it, I don't want to carry it. However, that means that even when I'm running out for a quick errand, I have to carry around a massive handbag with a wallet and keys sloshing around loudly. But I also need to make sure I can fit my iPhone, a couple of lipsticks, and a sunglasses case. I would probably also have to get a smaller wallet or cardholder because my wallet right now is an absolute behemoth.

This might be my new list of requirements for my next handbag investment, whenever it happens:

• Must have a crossbody strap, whether it's removable or not. 
• Should be in some neutral, non-white or cream color. Try to stray from black, if possible. 
• Roomy enough for a new essentials, but not another behemoth of a bag that can fit the entire world into it. 
• No impulse buying!

What's your dream handbag?