The 5 Best Designer Bags I've Ever Bought and Why

Okay, as someone who has loved fashion all my life and has been working at Who What Wear for the last 10 years, I have seen, researched, and ultimately bought my fair share of designer bags. I won't give an exact number (mostly because I'm too scared to count), but let's just say it's enough to know a good one when I see it. I am very proud to say that very few of my luxury purchases have ever been followed by regret.

Thanks to a combination of intuition and effort, I've built a collection I'm proud of. While I love all my pieces, I won't pretend like some aren't better than others. After all, not all handbags are created equal. On that note, I thought it would be fun to share the five designer purses that, at this moment in time, feel like the best of the best to me, from a little pouch by The Row that meshes seamlessly with every look to the Chanel Flap I'll never get tired of. Just keep scrolling to see my favorites (in no particular order), read about why I love each, and, of course, shop each style if you're convinced.

Loewe Puzzle Bag

I've had this black Loewe Puzzle Bag for over eight years and can honestly say it's still one of my favorite pieces I own. Aside from the unparalleled craftsmanship and eye-catching shape, I love it for how functional it is and the fact that it has never felt old or outdated to me. In fact, it feels cooler and cooler every time I look at it.

The Row 90's Bag

Something I don't do often is buy things on a whim, but when it comes to this bag, I did and am so happy about it. Knowing how quickly they can sell out, when I saw it in stock around this time last year, I ordered it without having a chance to think. Once it arrived, I knew it was a keeper. I love the shape so much that I actually have it in black suede, too, but this one is my absolute favorite thanks to the go-with-everything color that somehow manages to tie every outfit together.

Chanel Flap Bag

While I love my denim mini version seen above, I'm not going to get into specifics about size, material, or color here because I truly think that any version of this handbag is amazing. I own three, all of which are very different, and could never imagine parting with any of them. The good news, however, is that if I ever wanted to, I could probably turn a profit, as the value of these classic Chanel bags is constantly going up.

Gucci Jackie Shoulder Bag

This iconic shoulder bag needs little explanation, but let me provide a short one anyway. Whether you buy yours new or vintage, if you're looking for a classic bag that works for day or night and that you know you'll keep forever, this is it. I especially love it because it comes with an extra shoulder strap, so it can be converted into a crossbody for hectic days or when traveling. As I most often do, I opted for it in black, but truly, I love every iteration.

Khaite Lotus Tote

When I first bought this Khaite tote last winter, I admittedly was a little hesitant about it. I had originally purchased the larger size, but it felt too big to use comfortably every day—I'm 5'2", so I tend to buy smaller bags—so I returned it and went with the small instead. Since I loved the suede and shade of green so much, I decided to keep it, and after using it for a day, I'm pretty sure I wore it every day following for at least three months straight. Now it's still one of my most reached-for bags.