A man sitting on the bench wearing a suit and brown dress shoes holding a phone

The Shoe Cabinet of Chuck Bass

IlaydaBy IlaydaMay 17, 2020

What is the first thing getting in your mind when you hear the name ‘Chuck Bass’? Most of you, me included, are thinking: man, that guy knows how to dress.

For everyone who doesn’t know who Chuck Bass is, shame on you. Chuck is one of the main characters of the tv show ‘Gossip Girl’ and is viewed as a wealthy, eccentric, flamboyant, sly, and very desirable young man living on the Upper East Side. When there is one thing he is well known for, it’s his unique style. Who else would wear yellow trousers with a purple jumper (yes, he did)?

Gossip Girl is one of my favorite shows (I watched it 4 times….), and of course Chuck Bass is my favorite male character even after all the bad things he did and how he behaved in the first seasons. The best part of him is that you can clearly see how he is changing and becoming a better person after all the drama happening in his life.

I found many blog posts about his wardrobe and different style guides on how you can dress like Chuck Bass, but no one is really talking about his dress shoes. That’s why I want to give you insights about his shoe cabinet. I don’t want to give the game away, but let me say this: there are some eye-catching treasures.

Warning: Spoiler alert

Business in brogues

The costume department perfectly matched Chuck’s clothing to the personality of its character. It’s anything but conventional, unique, and cleverly calculated. Even his socks. In the whole show, Chuck experiments with different styles. He is well known for loving to spice things up. Even this is reflected in his style.


Chuck’s favorite shoes for running his business after the (presumed) death of his father are brogues. Thereby it doesn’t matter if derby or oxford shoes. In theory, brogues were adopted as an outdoor walking shoe. Their key feature is a series of perforations and is used for decorative purposes. This shoe is less formal the more broguing it has and vice versa. But we know Chuck loves to spice things up and mix classic business outfits with a more casual dress shoe. So, let’s move on to the first picture where he is wearing a plaid navy blue suit combined with brown full brogue derbies. In these shoes, he is confident enough to manage his meeting with the investors. Even during a walk with his dog Monkey, he looks professional and sharp in his blue wingtip oxfords. In the last picture, Chuck is wearing burgundy full brogue oxfords, matching the colors of his socks and tie.

Special Spectators


When I learned one thing during the research for my blog post then it is that Chuck loves his spectators. Especially in his leisure time. And who can blame him? These handsome shoes are anything but boring, just like Chuck. Special characteristics of spectators are the two different colors while it doesn’t matter if it is an oxford, a derby, or a loafer. In my last post, I recommended keeping all other pieces simple, so the shoe can shine. Surprise! Charles Bartholomew Bass doesn’t follow rules. He’s making his own rules by combining spectators with striking and unusual outfits. Even his cricket shoes look like spectator oxfords in brown leather and contrasting beige canvas. But seriously, who wears them with checkered knee socks and a plaid long-sleeved sweater on top of a shirt with a bow tie? While playing cricket? And still, looking good? Okay, let’s move to the second look: Combining his school uniform with blue and white full brogue spectator oxfords (what a long description), he looks like an innocent young boy in contrast to the third outfit. The brown full brogue spectator derbies work well with his striped trousers and checkered shirt. At first glance, the brown color looks like it doesn’t match with the outfit, but the second color takes up the color of his jacket and rounds up the whole look.



Okay, Chuck follows rules when it comes to oxfords. Because this is the type of shoe he wears on evening events and parties. The simple yet elegant style is characterized by its closed lacing system. Beginning with Chuck’s first look, he wears a navy blue suit and combines it with brown cap toe oxfords. To show everyone at the charity event that he is accompanied by his girlfriend Blair, the color of his shoes matches with her bag. For an outdoor party, Chuck reaches for a grey suit and white plain oxfords taking up the color of his shirt, always looking like a perfect gentleman with little details like his bow matching the color of the clutch of his girlfriend. At his wedding, the bride and groom switched the traditional roles, which is why Chuck is wearing white. And who said men can’t wear pink? To round up his look, Chuck decides for pink plain oxfords and looks stunning.

While watching the show, I never paid attention to the shoes the male characters were wearing. But after my research, I realized how much effort the costume department put into it. I mean, Chuck Bass is always wearing the same shoe model on certain occasions. Also, Chuck shows us that we don’t have to always stick to fashion rules but make our own. Feel free to dress how you want to and how you feel most comfortable with. Let me know in the comments below which of Chuck’s shoes are your favorite.