If my calculations are correct, Taylor Swift is headed for a bit of an image conundrum. She’s built a massively successful career out of being a lovesick teenager, but eventually both she and her fan base are going to age. Singers who find stardom in their teens have a notoriously difficult time making the jump, but based on these photos, I have high hopes for Taylor.

Swift is well-known to have some of the, err, tightest management in the industry, and they aren’t going to let their livelihood slip in to obscurity. The process of turning Taylor into an adult has to be a slow and careful one, but a fluttery skirt and prim sweater paired with a Fendi Anna Shoulder Bag, all in fall colors, are a perfect combination to bridge the gap between tweendom and adult stardom. A lot of women her age would be well-served to take a cue from this ensemble.

Bag Taylor’s Fendi Style via Nordstrom!

Have you guys heard the crazy rumors that Taylor Swift is dating Jake Gyllenhaal? That can’t be true, right? RIGHT?! For some reason, if it’s true, it freaks me out. They seem vastly different and I honestly thought they were much further apart in age than Wikipedia claims they are (nine years – Taylor is 20, Jake 29).

But honestly, it just kind of makes me feel bad for (and jealous of) Taylor. Her audience (and her marketing team) seems to wants to see her as an eternal teenager, which makes it difficult for her to have relationships with established stars or change up her personal style. She’s at an age where most girls are experimenting and discovering what they like to wear, but she always looks very conservative and young, like in these photos with her Lauren by Ralph Lauren Larchmont Crossbody Bag. Or maybe this is how she loves to dress and I’m way off base – she certainly looks normal and reasonably happy. But what’s the fun in being a celeb if you can’t be a little abnormal?

Bag Taylor’s Lauren by Ralph Lauren Style via Bloomingdale’s!

Is it just me or has there not been a lot said about Taylor Swift lately? This isn’t necesssarily a bad thing, I just became so accustom to hearing and reading about her all the time that I am at a bit of a loss when I came across these images of her.

Taylor was spotted with a small entourage while doing a bit of shopping in LA a few days back. She was all smiles and looked casually put together carrying her soft yet colorful Gerard Darel bag. Personally, the floral dress and the floral bag are a bit too floral for me. I wish that she would have paired the gorgeous Gerard Darel bag with a less busy outfit, but hey, whatever floats her country singing boat.

Shop Gerard Darel via GerardDarel.com!

So, The Costume Institute Gala is commonly known as the one of the most, if not THE most fashionable night of the year. Hey, this isn’t just my opinion, if you’ve had a chance to catch any of the footage from the red carpet, many celebs in attendance said the same thing.

Taylor Swift must have gotten the memo because she found herself attending the event in a glam yet whimsical gown by Ralph Lauren. The ivory Ralph Lauren Collection plisse georgette gown was soft, feminine and boasted beaded detailing. Taylor slipped on a pair of Ralph Lauren platinum metallic strappy heels and Fred Leighton jewelry to finish her look.

We’ve seen Taylor on several red carpet events and she is always dressed to impress. While this number isn’t too over the top or vamped up, I like it. I would like to see her change up her hair at these events, but hey, I’m not going to be that picky.

Shop Ralph Lauren via Saks!

Well wasn’t Taylor Swift just one of the top “it” girls last year? Everywhere you turned you would see her somewhere. I personally find her rather refreshing and sweet but I know some others have gotten really sick of her. No matter what your stance, you kind of have to be happy for her and all of her success.

Taylor made her way down the red carpet in a Kaufman Franco gown that was full of sparkles. I saw Taylor in an interview before the 2010 Grammy Awards Show and she was asked how she picked out her gowns. Her response was something along the lines of the more sparkle the better. Luckily she picked the right way to do sparkle, not the wrong. This gown is gorgeous! She finished her look with Lorraine Schwartz jewelery and Christian Louboutin shoes.

Shop Christian Louboutin Shoes via Net-a-Porter!

Let’s get one thing straight about last night’s Grammy Awards: Lady Gaga was ROBBED. Taylor Swift may be cute in an aww-shucks kind of way, and she might have some passable ripped-from-my-teenaged-diary type of songs, but no one has done more to make popular music interesting (and FUN) again in the last year than Ms. Gaga. Where’s Kanye West when we need him?

I don’t begrudge the teenager her Grammys, but just like Avatar shouldn’t have won Best Picture at the Golden Globes, I think that the people that voted could have made a better decision. What Gaga will always win, however, is the red carpet – despite not capturing the major awards for which she was nominated, pictures of her wearing this fantastic Giorgio Armani creation, made just for her, have been the lead in every article that I’ve read today about the ceremony. Ultimately, in a business like show business, the awards don’t mean much – all that matters is who is being talked about the next day. With a gravity-defying dress, the two-tone hair of a comic book superhero, and the fiercest eye makeup that I’ve ever seen on her, Gaga has absolutely captured that prize.

So go ahead, flame me for being mean to Taylor Swift. I’m on Team Gaga.

You know, that entire Kanye West outburst thing might have actually helped Taylor Swift’s career. While, yes, she is a completely talented singer/songwriter, it’s like since the outburst, everyone and their mother has become a Taylor Swift fan. I’m not finding fault, it is just an observation of mine.

Taylor has been spending some time in London recently and has been photographed looking casually cool and carrying the same bag more than once. We covered Taylor hanging with friends on the streets of London carrying a green French Connection Stitch Bag which she is also carrying here. This time, she is leaving her London hotel, smiling for the cameras, waving to her fans and winning people over with every second that passes.

Bag Taylor’s French Connection Style via French Connection.com!

These photos of teen country music sensation Taylor Swift practically yell out to me why she is so adored, in the country music world and beyond. She seems like such a nice and likable girl, one who’d be the perfect friend to bond with at late-night slumber parties. We already know she gives great advice to BFF Selena Gomez.

One of my pals is quite the fan of Miss Taylor, finding her relatable quality to be what most pulls him towards her songs, which are all written personally. That’s right, she pens them all herself, which is no easy feat in this media-infused, celebrity-obsessed culture of ours. It’s also no easy feat to stay down to earth in the wake of instant celebrity, but Taylor has done a marvelous job of it.

Even her choice of bag shows how relatable she seems: it’s the cute green French Connection Stitch bag, which retails for a mere $118. No status handbag for this girl! She’s staying true to her roots, totally emanating that girl-next-door aura- plus she’s rocking the most awesome little-old-man shoes in a completely fresh way. Yes, I think I’ve been won over by this gal.

Bag Taylor’s Style via French Connection!

Ok, honestly, it is about flippin time that Kate Gosselin changed that hair “style” of hers (and I use the term style very loosely). Regardless, the disaster that is Jon and Kate continues to spiral out of control. We are in the midst of one of the biggest he-said-she-said media wars I’ve seen in quite a long time. Wouldn’t you agree? And no matter how much of a train wreck this is, we can’t stop watching, reading and waiting to see what happens next. My only hope is that these 8 kids will come out of it as trauma free as possible. Guess we’ll have to check back about this in say 15 years or so.

Here, Kate was photographed carrying a signed poster of Taylor Swift, whom she interviewed while co-hosting The View. I hate to sound so skeptical, but while she is doing that and Jon is out in Vegas or LA or wherever, who is watching the kids? Either way, Kate was spotted with not one, but two black bags. Unfortunately, I don’t have an ID on either of them. Anyone have any ideas? I heard that the bag on the right reminded someone of a bag she saw on QVC. Do you agree?

Kanye West needs to simmer down. For those of you who watched the Video Music Awards (VMA’s) last night or have read up on what went down, you know that Kanye got up on stage during Taylor Swift‘s acceptance speech for her very first VMA. Kanye, after being sipping on an entire BOTTLE of Hennesy, took the mic from Taylor and announced how he thought Beyonce should have won. Hey, Kanye, we all have our own opinions and sometimes it is best to keep them to yourself.

Well, don’t worry about Taylor, she has been nothing but graceful and gorgeous through the entire thing; she’s saying nothing bad and continues to talk about what a great night it was. I love when people take the high road.

While these pictures weren’t shot at last night’s award ceremony, Taylor Swift was sitting pretty during a photo shoot in London’s Notting Hill area just a few weeks ago. Red attire, red lips, red nails all come together for one, red hot look. I realize it is a photo shoot, but it takes a real beauty to pull of this look. Nice job Taylor… and don’t worry about that Kanye thing… people are behind you!

Taylor Swift has burst into the music scene and found her way to the top of the charts. Swift, merely 19 years old, is also known for being BFF’s with American Idol’s Kellie Pickler. Taylor Swift and Miley Cyrus’ sister have had something in common the past few weeks: they both continued to be snapped carrying the same bag. IDing this bag stumped many of us on Purse Forum, but our search finally lead us to ID the bag as SL McFadin. The designer is little-known in the handbag world, but it seems that Swift and Cyrus picked up this bag at the American Country Music Awards in their gift bags from Backstage Creations (more here). Fringe is in for summer and Taylor Swift paired her SL McFadin brown fringe bag with turquoise shoes while in DC on her way to the airport.

Bag Taylor Swift’s SL McFadin Fringe Bag at SL McFadin online!