No matter whether you want to visit New York Fashion Week, to see the real life Gossip Girl sites or just to glam up anyway, NYC is an absolute fashion haven. If Serena, Blair and others from the Gossip Girl world are your style icons, then I’ve got a must have Gossip Girl outfits guide for you.
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Table of Contents
Blair Waldorf Outfits
My personal favourite icon when it comes to Gossip Girl fashion is Blair Walrdof. Her outfits are always classy, with a slight touch of sass and a lot of confidence.
The Blaid Waldorf style is youthful, timeless and modelled after Audrey Hepburn, which she adores.
Throughout the series her styles in Gossip Girl change from the school girl look with shiny headbands, patterened tights and mini skirts to more elegant high end business-style attire.
Think preppy meets bossy. Understated jewellery and low heels. In the evening, ball gowns are a way to make an entrance.
To see the following picks of Blair Waldorf looks you can recreate for your Gossip Girl outfit selection, disable your adblocker for this page.
Day dresses – Audrey Hepburn is Blair’s favourite style icon, it’s no surprise to see this influenced in her choices for outfits on Gossip Girl.
Etui and fitted monochrome dresses are therefore a staple and you can find them in many but mostly monochrome colours.
Another go-to outfit for Blair are slight hourglass shape dresses*, referencing the “effortless” look of the 50s. Also, consider wearing dreamy lace dresses*, which are great for the hot NYC summer days.
Headbands – In the first seasons, you couldn’t catch Blair Waldorf dead without her signature headbands.
For $325 you can even get one of the original Blair Waldorf pieces made from Swarovski crystals. If you don’t have that kind of money, get a cheaper bridal headband* or an affodable rhinestone headband*.)
Blouses – Blair isn’t a stranger to pencil skirts and flowy blouses, often made of silky materials. Here, she also deviates from her typical simple colour looks and also integrates romantic patterns or big statement ribbons.
Coats – Blair looks great no matter the weather but she’s also concerned about her health and coats are a great way to look fashionable AND stay warm. Alternatively, she loves to wear fitted blazers, sometimes made of tweet like with Chanel jackets*.
Flats – Comfortable during long strolls at the MET, through Central Park or among the shopping streets, flats* are Blair’s preferred shoe choice. After all, they were basically invented for Audrey Hepburn, so they must be a staple for Blair, too.
Tights – In the end, Blair’s style is leaning more towards the conservative. Hence, the many tights. a lot of them come with patterns, are either black or white*.
Sometimes they provide a pop of colour when the Blair outfits in Gossip Girl require them. If Blair wants to crank up the heat, she picks stockings with lace details*.
Lingerie – For hanging around the house on days when you just don’t wanna leave, forget sweat pants if you’re Blair. For her “casual” outfits on Gossip Girl, Blair Waldorf wears sexy black lingerie and negligees* with a throwover.
Handbags and pouches – Blair’s clothes are usually colour coordinated. This reflects in heels, headbands and, of course, handbags* and pouches*.
Her handpicked pieces are designer bags and look super chic but sometimes also colourful*.
Gowns – Blair’s ball gown choice is very fairy tale like. Think Princess wedding (which she nearly had) and in pastel colours or simple black.
Blair goes all out in her gowns* as if there’s a ball wherever she goes. To me, Blair’s gowns are some of the best outfits on Gossip Girl.
Fascinators – If it’s a very special occasion, her headbands get an upgrade and become proper fascinators or extra sparkly pieces.
Heels – Blair can also rock a sexy heel though they are usually black or bedazzled. She’s Queen B!
Serena Gossip Girl Outfits
Serena is an It Girl through and through. But sometimes she is a little bit of a trainwreck as well. She’s all over the place and constantly trying to find her identity, gain core confidence and sort her values.
This reflects in her clothing choices as well. Sometimes she dresses all femme fatale, other times in an elegant bohemian-style. She alternatives between tight-fitted dresses and lose pant looks.
But one thing is for sure, every Serena van der Woodsen outfit has that certain wow effect, whether it’s day or night.
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Body con dresses
Serena loves to look tempting all day every day. She’s always tastefully chic but always revealing. Body con dresses are a great way to show off her toned figure.
Maxi dresses
Whether for upper class picnics or the races, Serena’s Gossip Girl outfits make her look dressed to impress. With long, flowy boho dresses* Serena can throw on easily, she expresses her carefree nature.
Ball Gowns
Serena’s favourite colour seems to be gold, even for her wedding gown. Before that though, she was often seen wearing glamorous gold evening gowns*. Other colours of choice are black and creme.
Heels – Serena is daring when it comes to her choice of heels. Normal pumps won’t do for her, she goes all out. Be it sparkly colours, straps, rhinestones or platform sandals. She’s ready to party.
Jenny Gossip Girl Outfits
I feel like Jenny Humphrey had three major fashion phases. The first one was cute girl next door, the second was grunge bitch and the latter rock n roll fashionista. Do you agree? Drop me a comment.
Mini shorts and skirts – Much more risque than Blair, Jenny wanted to stand out and be known. Going directly against Blair’s more conservative and subdued style, hers was loud.
Shorts were super short, legs super long. School skirts* went up as well as part of her daily Gossip Girl outfit.
Tie heels and boots – Shoes quickly became Jenny’s signature piece. Just look at he massive tie heeled boots* and overknee boots she showed off her fishnets in.
Hats – Jenny’s Gossip Girl outfit featured a variety of hats, starting with cute beignets* and transferring over to monochrome beanies* when she got her couldn’t-care-less attitude.
Tartan – Not a piece of clothing, but a choice of patterns. Jenny seemed to love tartan*, no matter if originally in colours or later in a monochrome palette.
Be it on kirts, shorts, hats or cardigans. Tartan pattern had quite a lot of screen time in Jenny Gossip Girl outfits.
Big hair – Jenny’s hair was always in waves and the more the series went on, the wilder it got.
It perfectly encapsulated her attitude and mental state throughout the series. To keep it even looking purposefully unstyled, Jenny had to use curl defining products*.
Leather accesories – Piling black on black, Jenny knew how to make every look rock n roll. Studded bracelets or handbags*, leather kit gloves* or heels*.
Dark makeup – Jenny didn’t have a goth style but she sure liked make up that was dark and bold. Racoon eyes* and deep red lips* were her trademark finish for her Gossip Girl outfits.
Evening dresses – Jenny’s dresses quickly turned from cute Cinderella pastel dreams to Maleficent on a night out*. Sometimes, she paired her dresses down with a leather jacket*.
Goth gowns – Not sure how else to say it but Jenny managed to make Goth grunge chic ballgown ready*.
Lily Gossip Girl Outfits
Lily’s style is timeless. She looks like a trophy wife but is far from just that. No matter who she is married to, she is her very own person and a strong and influential woman.
Even though she tries to stay out of all the rumours and scheming of the Upper East Side, she can serve it if she needs to protect her faimly. Her looks are always tailored and easily transition from day to night.
Sculpted dresses
She means business and this is reflected in her daily attire as well. Fitted and etui dresses* perfectly match Lily’s style. With those, she looks utterly glam but still understated.
Jewellery – Lily loves necklaces that work with every outfit. Sometimes this includes understated simple pieces, mostly tough major statement pieces, such as heavy stone necklaces* and big shiny rings*. You will always know: her jewellery* is worth a fortune.
Coats – Minimalist, clean cut coats*, monochrome ponchos* and jackets* are Lily Humphrey/Bass’s jam. She looks like a picture of sophistication and the tailoring is part and parcel of it all.
Statement handbags – Whether it is a Hermés or Birkin bag, none of Lily’s Gossip Girl outfits is complete without a designer handbag*.
Like the majority of her wardrobe, the tones are muted and the designs sharp. There is no playfulness there.
Pumps – Does Lily ever wear flat shoes? She is rocking a heel* in strides. And they are always sky high, just like her standards.
Evening gowns – Lily loves fitted dresses just like her daughter. But for her, they have an added glam factor to it.
Simple black evening dresses* turn dazzling with sequins and crystals attached to them. Many of Lily’s Gossip Girl fashion choices also sport asymmetrical cuts, such as one sleeved pieces*.
Georgina Gossip Girl Outfits
Georgina Sparks was rather a scheming devilish character in the Gossip Girl series. Not surprisingly, you will often find here dressed in black and silver, cold colours, as well as wearing smokey eyes.
Mini dresses* – Georgina loves to show off her long legs and chooses short dresses. Many of those are in silver colours, glamming up even otherwise simple black outfits.
Leather jacket – Georgina Sparks is a wild one. Her leather jackets* speak volumes. You never know what she’s got up her sleeve. (Ok, I stop with the jacket puns.)
Anyway, her styles make for a really practical and well dressed New York City packing list.
Leggings and fitted jeans – Blair absolutely despised wearing leggings as pants. But Georgina didn’t care about such things. She’s a (fashion) rebel and extended her edgy style even to black* or patterned leggings* If not leggings, the jeans she wore were super tight as well.
Sunglasses – You never knew what Georgina Sparks was up to. So the wardrobe translated this to her wearing pitch black shades* – big Nicole Richie style ones.
Body con – Georgina Sparks is a seductress and her dresses show this. Sexy in black or red, she knows how to make her porcelain skin and red hair shine.
Killer heel – Georgina Sparks does nothing but aim high. Just look at her killer heels! She’s out hunting.
Lip stick – Taylor Swift could have said this about Georgina’s Gossip Girl outfits as well:
“Lipstick on your face / So it goes… / I’m yours to keep / And I’m yours to lose / You know I’m not a bad girl, but I / Do bad things with you” Georgina loves all shades of red on her lip, preferably dark and matte*.
Smokey eye – Perfect black eyeliner* or smokey eye shadow*, Georgina doesn’t ever go colourful. She’s above that.
Photo credit: Andre Benz, Celio Michon, The CW/Gossip Girl Wiki [1], [2]
Should You Pack Gossip Girl Clothes for NYC?
Well, if you want to really feel the Gossip Girl vibe in NYC, you might as well dress up. It’s fun to stroll through the streets of Manhattan looking all Upper East side – even if you could never afford to live such a lavish life.
The outfits and lifestyle were seriously expensive but luckily you can look like a million bucks even with affordable pieces. With inspiration from the Gossip Girl clothing, there’s nothing in your way.
And it’s well worth it to dress up for NYC. Just maybe don’t walk around in heels all day long. You’ll feel like dying. Especially if you want to sightsee NYC (on a budget) and see NYC’s best photo spots, you need to take care of your feet. You’ll need them.
Which is your favourite Gossip Girl outfit?
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