Style Triple Shot: Caitlyn Jenner in NYC

Posted on July 01, 2015

Let’s talk about Caitlyn’s style, shall we, darlings? Let’s also talk about T Lo, because that’s our favorite topic in the world.

Yesterday, we featured Miss Caitlyn out on the town, attention-seeking like the E! reality star she is, and offered some mild criticisms the same as any we’d make for any woman wearing an outfit like that in her age range and with her body type. There was no explosion of outrage or anything like that, but we could feel from the responses both here and on social media that people were seizing up at the idea of criticizing her looks. But here’s the thing from our perspective: While it’s true that she has become a spokesperson for a cause and in many ways an inspirational figure and even role model, for the purposes of this site and our own perspectives, we’re going to see her as very wealthy and attention-seeking ladystar with a very flashy personal style and a need to promote herself because she’s got a new reality TV show coming out soon. She can be both things at once, but since you come here for the celebrity style talk, that’s the side of her we’re looking at.

When Laverne Cox hit the scene and we found ourselves regularly writing about the style choices of a transgender woman, we assessed our approach to make sure we weren’t bringing any preconceptions or prejudicial thinking to our writing and found that there was one simple way to keep our thoughts true. All we had to say – and we only had to say it once or twice before it stuck – is, “She’s a woman.”

Not a transgender woman, although that’s what she and Caitlyn are. But for style purposes and for this site in particular, it’s important to us that we write about women like Laverne and Caitlyn in exactly the same manner we’d write about their contemporaries like Beyonce and Helen Mirren. We’d be doing them a disservice if we treated them any differently, frankly. We don’t say this to erase their trans identities and we sure as hell don’t say it to pat ourselves on the backs, but Caitlyn’s clearly on the poledance at the moment and her decades as a Kardashian family member have rendered her WORLD CLASS in that regard. There’s no need to treat her like a saint. She’s sporting tons of free designer clothes (WAY more than Laverne gets, we’ll note), dressing like a Real Housewife on an AmEx bender and working the press and the paps like the Olympic level attention whore she is. Like everyone else in her extended clan, she WANTS you talking about her.

So let’s get to work and JUDGE, kittens. Because that’s the other thing: girlfriend needs a stylist badly.


Caitlyn-Jenner-GOTS-NYC-Street-Style-Diane-von-Furstenberg-Tom-Lorenzo-Site-TLO (1)Caitlyn Jenner seen out and about in NYC in a Diane von Furstenberg leopard print wrap dress paired with black slingbacks.

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The dress works really well for her, although it’s another instance of a sleeve length that isn’t quite working for her. She looks pretty damned toned to us and she certainly has no problem showing off her legs, so we’re curious as to why she seems reluctant to uncover more of her arms.

The accessorizing isn’t good. She clearly loves those slingbacks, and while we’re sure the range of shoe options are limited for her size (although she’s crazy wealthy, so that shouldn’t be too much of an issue), she needs to open things up a bit more. The black accessories don’t read as daytime and the dress needs something to keep it a little on the playful side. A pair of wedge heels would’ve been our choice. And a brown or white bag.



Caitlyn-Jenner-GOTS-NYC-Street-Style-Diane-von-Furstenberg-Tom-Lorenzo-Site-TLO (5)Caitlyn Jennerspotted leaving the Patricia Field store in NoHo, NYC in a multicolored sequin mini dress paired with a black blazer and slingbacks.

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Now see, here is why you come to us. For the blunt assessments that the big celebrity and fashion sites (who all praised this look) won’t give you. This is awful and we have no problem saying it. She’s working her way through a style evolution and trying to figure some things out, sure. But she’s got more cash than she knows what to do with and could hire the best stylists in the business to guide her away from mistakes like this. It’s all way too try-hard. The jacket, dress and bag don’t go together at all and every piece looks too drag queen or trend whore. We’re all for her expressing herself and more power to her if she wants to dress like a cross between a Playboy model and Edina Monsoon, but for sidewalk sashay purposes, we’re gonna call it like we see it. This is a bad look.



Caitlyn-Jenner-GOTS-NYC-Street-Style-Diane-von-Furstenberg-Tom-Lorenzo-Site-TLO (9)Caitlyn Jenner seen arriving for Broadway play “An American in Paris” in NYC in a Diane von Furstenberg ‘Julianna’ three quarter sleeve lace wrap dress paired with black slingbacks.

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This, on the other hand, is the best thing she’s ever worn, as far as we’re concerned. She looks sexy and pretty and the dress looks great on her. She is much better off when she shoots for softly feminine over fierce-as-fuck. This is what a good stylist would tell her. Just as they would tell her to stop finishing off every look with the same boring shoes and bag. This is one lady who needs some serious lessons in the art of accessorizing.
[Photo Credit: RGK/PacificCoastNews, PacificCoastNews]

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