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Gossip Girl Fashion Retrospective: Chuck Bass, Then & Now

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Chuck Bass from Gossip Girl wearing a pink gingham shirt, beige blazer, and bow tie in an outdoor setting
Photo Credit: Kelly Rutherford on Instagram

It’s day three of our walk down Gossip Girl memory lane, and that means it’s time to talk about the fashionable world of Charles Bass.

Ah, Chuck. That smirk, that scarf, those daddy issues! And man, can the boy dress. Always dashing but never too flamboyant, Chuck’s wardrobe has grown beyond the loud colors and wild prints of an insufferable rich kid, to the impeccable closet of a dignified, refined young man. Let’s take a look at the outfits!

Naughty Schoolboy

Outfit inspired by Chuck Bass's pea coat and checked red and white scarf: black peacoat, green skinny pants, beige blouse, plaid scarf, brown oxford pumps, and red stud earrings
Peacoat, Blouse, Pants, Scarf, Oxfords, Earrings | Photo: The CW

It’s hard to imagine that there was ever a time when Chuck dressed like an average dude (aside from his signature scarf, obviously). But while at St. Jude’s, Chuck actually followed the dress code. With a few added twists, of course.

Get the NYC prep look by experimenting with bold, classic colors and shapes. Chuck’s early color scheme seems to be a nod to Ed Westwick’s British roots, so stick to navys, deep reds and greens, with subtle pops of light yellow. Pair a basic collared blouse with emerald skinny pants, and don’t forget your scarf! I chose a preppy plaid print, but I think Chuck would be open to plenty of experimentation. Accessorize with brown oxford pumps and bold red studs. Top the whole thing off with a stunningly simple black peacoat.

Bold & Preppy

Chuck bass look 2 with yellow pants, pastel blouse, purple cardigan, bow necklace, polka dot bag, and tan brogues
Blouse, Pants, Cardigan, Bag, Brogues, Necklace | Photo: The CW

As time wore on, Chuck really started to distinguish himself from Nate and Dan’s classic uniform look. He kept the preppy style, but really brightened things up, color-wise. And when I say bright, I mean bright. If you didn’t know him any better, Chuck’s outfits might look a little clownish, but we know the truth. It takes a man with real taste to wear baby blue, shocking yellow and deep purple all in one look!

Snag Chuck’s preppy brights by experimenting with color. Purple and yellow look amazing together because they’re opposite from each other on the color wheel, so don’t be afraid to mix them. Rock bold yellow skinny jeans and a royal purple cardigan layered over a pastel collared blouse and you’ll be Chuck’s new protege in no time. Accessorize with classic pieces that have a preppy twist, like tan brogues and a polka dot cross-body bag. Complete the look with a bow-tie-shaped necklace.

Real (Business)Men Wear Pink

Chuck Bass-inspired outfit with pink blazer, white peplum blouse, navy chinos, coral scarf, black pumps, black satchel, and a gold watch
Blazer, Blouse, Pants, Scarf, Pumps, Bag, Watch | Photo: Pacific Coast News

In the wake of his father’s death (or so we thought…) Chuck gained control of the family business, and seriously matured in both style and attitude. Though I like to think his fashion inspiration was all Blair’s doing, you have to admit, Mr. Bass came into his own.

Get Chuck’s smart but still playful look by rocking a baby pink blazer over a white peplum blouse. This gives you the perfect balance between fun and sophisticated. Navy chinos keep the look business-like, while a coral scarf livens things up a little. Keep your accessories polished and classic – a structured black satchel, matching pumps, and a heavy gold watch complete this menswear-inspired look.

Bass Industries

Chuck bass style with plum peplum dress gray blazer lavender clutch black flats and gold bow earrings
Dress, Blazer, Clutch, Flats, Earrings | Photo: The CW

Chuck’s maturation continued throughout the later seasons, as he lost his company, and Blair, over and over again. (Seriously, you guys? Get it together.) Gone were the days of bright hues and fun accessories galore – they were replaced by somber (but stylish) suits with subtle pops of color. Guess he really is all grown up!

Channel Chuck’s well-tailored look with a gorgeous plum-colored peplum dress worn under a structured gray blazer. Keep your accessories simple but classic. Black ballet flats and gold bow studs radiate simple elegance, while a lavender snakeskin-print clutch adds that subtle pop of color that Chuck rocks so well.

Your thoughts?

What’s your favorite Chuck look? What do you think will happen to him in the finale? Be sure to leave me a comment and let me know what you think – I’d love to hear your thoughts!

Posted on on December 16, 2012 / Filed Under: Inspiration / Tags: , , , , , ,

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18 Responses to “Gossip Girl Fashion Retrospective: Chuck Bass, Then & Now”

  1. 1
    December 16th, 2012 at 4:32 pm

    Wow, I’ve never followed Gossip Girl before but this series is making me want to start! What a fashion icon Chuck is, I’d wear any of the above outfits! Thanks for the great posts Carina!

  2. 2
    December 16th, 2012 at 4:53 pm

    Chuck Bass will forever be my favorite character in television history. He’s so wonderfully complex and imperfect. Thank you so much for this post in the series, he is definitely a fashion icon everyone should take inspiration from!

  3. 3
    December 16th, 2012 at 5:00 pm

    You are a beautiful person. I love Chuck Bass, I love his style, and I love the outfits you’ve put together. So excited for the finale! I have two more episodes to watch first, if I ever get a break from finals…

  4. 4
    December 16th, 2012 at 6:43 pm

    I’ve never watched the show, but I love this guy’s fashion. (not the girl versions, but his actual clothes)

  5. 5
    December 16th, 2012 at 7:13 pm

    What a diva. Work.

  6. 6
    December 16th, 2012 at 9:03 pm

    Can you please do a series about “what petites should wear”?
    Thanks you~ :)

  7. 7
    December 16th, 2012 at 10:55 pm

    Love this post! Chuck will forever be one of my most favorite television characters. However “never too flamboyant?” Are we forgetting the red zip up onesie sweat suit of last season? :)

  8. 8
    December 16th, 2012 at 11:15 pm

    I like the translation of Chuck’s outfits from male to female :) There are some fantastic very sharp looking pieces in this post! Love the coat and scarf in outfit one and the pants and shoes in look three would be fantastic for work! Nice job :)

  9. 9
    December 16th, 2012 at 11:50 pm

    Glad you guys like! Chuck is one of my faves :).

    @Mady
    The onesie!!! How could I forget… I’ll admit, that was pretty ridiculous.

  10. 10
    December 17th, 2012 at 4:18 am

    awesome post!! I love chuck and his style
    hahaha, but yes the onsies were ridiculous :P and so weas the outfit with the purple head and wrist band he wore in ‘Bad News Blair’
    sometimes it was just hard to take him seriously when he wasn’t wearing his fabulous suits ;)

  11. 11
    December 17th, 2012 at 2:02 pm

    Chuck is my favourite character and I love him and Blair! I hope that in the finale they will finally end up together!

  12. 12
    December 17th, 2012 at 4:36 pm

    Awww, it’s Chuck! :)

  13. 13
    December 17th, 2012 at 6:14 pm

    OMG This has reminded me of the old time of Chuck Bass, he was so sexy back then! don’t get me wrong, I still love him but I will always love his first looks, when he wore his signature scarf.

  14. 14
    December 17th, 2012 at 6:54 pm

    I <3 Chuck and i'm really going to miss this show I started watching it from the start and now its gone omg how will I live. He's style was always a standout this is how a man should dress

  15. 15
    December 22nd, 2012 at 10:08 am

    I really don’t understand why people idolize this character. He’s abusive towards Blair and has tried to rape several of the girls on the show. Not to mention he sold Blair for a hotel. I just don’t find him appealing at all.

  16. 16
    June 6th, 2013 at 3:52 pm

    Love him. Great, complex character with unparalleled style and fashion sense.

    @Steph he’s a classic anti-hero that spent the last two seasons growing up and being redeemed. Why people bring up the things Chuck did in the past when he clearly made up for them and became a wonderful husband and father by the end of the series is beyond me. He’s loved because he’s sexy, complex and changed because of his love for Blair. What’s not to love? :)

  17. 17
    December 16th, 2013 at 6:22 am

    That guy with the scarf isn’t even Chuck… It’s just someone posing as him.

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