Olivia Palermo amuses me for a lot of reasons. First, I don’t really understand what she does for a living, although I remember that she started a blog, which garnered her a lot of press like it’s not something that attractive, fashionable women her age do every day. Second, she was on The City, and everything related to MTV reality shows amuses me in one way or another. Third, and most importantly, I remember how she got famous the FIRST time around. Before she was fashion famous, even before she was reality TV famous. She was Gawker famous.

You guys are probably all familiar with Gawker now, but a few years ago, it was more of an insider-y New York City media and society rag than a generalized US gossip blog. Back then, Olivia Palermo was a budding social climber, apparently hungry to get noticed in the New York socialite set, and Gawker obtained an email that she apparently sent to every vaguely noteworthy social in Manhattan, more or less begging them to be friends with her. To this day, that’s the first thing I think of when I see pictures like these, where she’s gallivanting around the city with her pup and her Christian Dior Lady Dior Shoulder Bag. More than anything, I’m impressed that she managed to change her own narrative so effectively after that first brush with public humiliation.

Bag Olivia’s Dior Style via Dior!

We all know that I’m no huge fan of former The City star Olivia Palermo, but every now and then she wears something that makes me excuse her existence for a moment. In this particular case, it’s her totally fun blue and yellow Cesare Paciotti Sandals. I love a whimsical shoe, and these look like they were made for a comic book heroine.

I’m not quite as much of a fan of her grey wool Giambattista Valli jacket, but I do respect someone who’s willing to wear unconventional shapes and play with proportion. But let’s be completely honest here – her gorgeous boyfriend is too distracting for me to think in any serious way about her shoes or jacket.

Bag Olivia’s Cesare Paciotti Style via Zappos!

For purposes of handbag science, we’re going to ignore the fact that these “paparazzi” photos of former The City cast member and pop culture villain Olivia Palermo appear to be perhaps the most staged pictures in the history of fake paparazzi ambushes. In all of them, she looks positively delighted than anyone has shown up to take her picture. But that’s not important, even if it is kind of funny.

What I’m more interested in, obviously, is what she’s wearing. We know that her shoes are Charlotte Olympia Leopard Booties and her eyewear appears to be Dior Sunglasses, but what about that bag? It clashes with her outfit, but with a better pairing, it might be kind of a great everyday bag. I’ve scoured the internet and come up with nothing, but somehow, you guys always seem to have the answers. Let me know in the comments!

Bag Olivia’s Charlotte Olympia Style via Net-a-Porter!

I couldn’t really tell you what The City star Olivia Palermo does in her time away from reality tv – she doesn’t seem to have any aspirations of being an actress or Kardashian-type tabloid fodder, but surely she has to do something other than walk around with her gorgeous boyfriend and equally gorgeous Hermes Birkin. Although if I had a boyfriend that hot, I don’t know if I’d have any problems filling my time.

She’s being going to a lot of fashion shows lately, but those only happen a couple of times a year. Does she have a real job anywhere? Based on everything I’ve read, the “job” she has for the show seems to exist only for purposes of filming, so she can’t be spending all that much time in the office. Although I guess these same questions could be asked of nearly any of MTV’s celebutante bunch- she’s certainly not alone in that regard.

Bag Olivia’s Hermes Style via Hermes.com!

I try not to get too invested in the lives or personalities of celebrities, but I have to admit that these photos took me totally by surprise: why are Olivia Palermo and Emma Roberts friends? Have they always been friends? Are they working on something together, and that’s why they’re hanging out? I can’t find the answers to these questions, but I’d like to know, if anyone has the scoop.

I’m just not much of an Olivia fan, and although I haven’t consumed a great deal of Roberts’ work, it’s kind of a turnoff for me to see them hanging out like besties. Although perhaps I shouldn’t believe everything I see on The City – maybe Olivia is a totally reasonable and nice personal in real life? And not only are the two together, but they’re both carrying Chloe handbags – Olivia has the Chloe Gemma Bag and Emma is carrying the Chloe Elise Satchel.

Bag Olivia’s and Emma’s Chloe Styles via Saks!

You know what? While I am not a huge fan of Oliva Palermo (at least the way she seems to be portrayed on The City), she certainly knows how to dress. I don’t care where she is going or what she is doing, Olivia always and I mean ALWAYS looks put together.

Olivia and her hot, Hot, HOT boyfriend, Johannes Huebl, were snapped as they arrived at the 2010 Operation Smile annual gala in NYC. The event itself is hosted every year in order to raise money that will be used towards fixing cleft lips and palates in children across the world. This NYC power couple looked absolutely fabulous walking into the event. While I’ve seen the purple feather bag Olivia is carrying before, I can’t quite put my finger on what it is. Do you know?

I found this to be a very interesting piece of information. No, not the fact that Whitney Port was seen at the 1961 Show during Fashion Week but that she was sitting in the second row! See, I wouldn’t be that surprised, but fellow The City co-star, Olivia Palermo was at the same show, but in the front row. Sounds like that could have caused a bit of a rift. Well, actually, I bet Whitney didn’t have a problem with it as much as Olivia would have if the situation was reversed.

All drama aside, Whitney looks pretty gorgeous at the show. I love the combination of neutral colors that she selected for her look. I’m also a fan of her bag, but I can’t quite be sure what it is. At first I thought perhaps Valentino then maybe Be&D but I don’t have the best angle to work with. Thoughts? Oh and check out her shoes – I want them!!!!

I was not shocked in the slightest to see that Olivia Palermo was in attendance at shows during NYC Fashion Week. This NYC socialite is always spotted at premiers, shows and events that can be next to impossible to get into.

Here, Olivia was photographed as she attended the Ports 1961 Show in Bryant Park. Yet honestly, what was she thinking? There are so many looks and textures going on here I don’t know what to do with myself. Olivia is usually so sophisticated and well dressed I almost couldn’t believe my eyes. It is as if four different looks threw up on her all at once. At least I like her Be&D Genesis Bag. At least that bag is worth being spotted during Fashion Week. Olivia, you can do better than this!

Shop Be&D at Bloomie’s!

More pictures of Olivia Palermo and more pictures of a handbag I am not 100% sure about. With Olivia’s relatively dark looking outfit, it is no shock that her clutch popped out at my instantly. I wish I was able to zoom in, but my best thought is that she very well could be carrying a Carlos Falchi clutch.

But, let’s move on and talk about what I do know for sure. Olivia is pictured here as she attended the NYC screening of The Private Lives of Pippa Lee. I am a bit curious about Olivia’s attendance of these screenings and premiers. Do you think she was invited to as many as she is now before staring on The City? Either way, she attended this screening with boyfriend Johannes Huebl. While rather casual, Olivia’s attire is pretty well put together. Plus, finish it off with a great pair of Christian Louboutin pumps and you really can’t go wrong.

Bag Olivia’s Christian Louboutin Style via Net-a-Porter!

I haven’t always been the biggest Olivia Palermo fan. It’s not because I know much about her, but it is because of the way she actually is or the way she is portrayed on The City. For any of you who watch the show, you know what I am saying. Olivia just seems so snobby and she seems to walk around with the “I’m better than you and you should know this” kind of attitude. Yet no matter what you think of her, it’s hard not to admire her sense of style.

Here, Olivia is strutting her stuff through the SoHo district of NYC. Granted, she’s constantly being photographed, but this is one look that I am totally loving. Every single aspect of her look works. Actually, not only does it works, but Olivia kills it! I am dying to own the Missoni dress and the belt that she is rockin here. Now add the gorgeous Chloe Gemma bag and Christian Louboutin boots – drool fest! So maybe I will take the high road and just focus on her knock-out look.

Bag Olivia’s Chloe Style via Net-a-Porter!

Bag Olivia’s Christian Louboutin look via Net-a-Porter!

Sure, there are plenty of handbags that i struggle to identify. However, this is one bag that I can’t ID is annoying me! I’ve been working on trying to ID this bag that Whitney Port is carrying and after a couple weeks, I’ve got nothing. Everyone that has tried to help ID it has no idea either. So, help me out here, what is she carrying?!

While I don’t know which bag she is carrying, I do love her look. Since she’s been out in NYC, I’ve seen a bit of a style switch from her LA days. However, this look is the perfect merge of LA casual and NYC edge. A cute pair of jean shorts, an adorable top, great accessories and a fabulous bag. She looks amazing. I also have to say I am loving the dress her friend is wearing. I would totally rock that dress!

One more thing, I can’t wait for the new season of The City. Hopefully Olivia Palermo will chillax a bit. She was getting a bit on my nerves towards the end of last season, but hey, that’s just me.

Just about every post we’ve done about Olivia Palermo has included some mystery man by her side. Well, I am sure he wasn’t a mystery man to many of you out there, but I had no idea who he was. I just knew he was pretty – like REALLY pretty. Turns out the man Olivia Palermo has been spotted all over the place with is Johannes Huebl. This German born pretty boy is absolutely gorgeous. I was a bit curious as to how he and Olivia met, but turns out they are both socialites, so there you go.

Here, Johannes and Olivia were spotted as they entered the special NYC screening of Inglorious Basterds. I haven’t seen the movie yet, but I hear it is rather good. And not that I would ever be invited to one of these oh so special screenings, but if I were, I bet I would spend more time checking out the celebs, who they were with and what they were wearing than the movie itself.

Speaking of what celebs were wearing, I cannot figure out for the life of me what clutch Olivia is carrying. It reminded me a bit of a clutch we covered a while back on Purse Blog, but I am totally blanking. Anyone have any ideas? Prada, perhaps?