Lillian Celia “Lily” van der Woodsen is the mother of Serena and Eric in the Gossip Girl which aired from 2007 to 2012. Born into a prestigious family, Lily grew up in New York City’s Upper East Side, surrounded by privilege and high society, and spent her early years on the West Coast art scene after being kicked out of boarding school. Throughout the series, Lily is depicted as a complex and multi-faceted character. Despite her glamorous facade, she grapples with personal struggles and family dynamics, often with themes of independence and approval. Her relationships are often tumultuous, filled with secrets, betrayals, and reconciliations, creating many storylines throughout the show. Despite her flaws, Lily is fiercely loyal to her family and friends, willing to make sacrifices to ensure their well-being. She’s known for her socialite status, family reputation, many marriages, refined taste in art, and image..
There is not a moment where she isn’t well dressed, even in the first season when GG had a lower budget. The actress used her clothes, such as bringing her Birkin on set, to create a realistic image of an Upper East Side woman, we see the foundation of Lily’s looks. Classic, refined, high fashion. Lots and lots of staples such as denim, trench coats, scarves, and boots all in minimalist neutrals. Very New York with understated elegance in the day and glamourous appeals in the evening. Despite Blair and Serena being more renowned as the fashion trendsetters of Gossip Girl who I covered previously, Lily has a really timeless style that continues to be coveted and adaptable for everyone. We can all take a page out of her book.
While some may describe her style as embodying “quiet luxury” I believe she practices stealth wealth. If you’re unsure of the difference I have previously covered this in my Shiv Roy style analysis. But for example in this scene scene, Lily is sporting a stunning sheath dress, with embellished beadings that make up the sleeves in a monochromatic tone. It is finished off with the Appolon Swarovski ring, and diamond drop earrings paired with a glass smokey bubble bead necklace. Very avant-garde and high fashion, but also wearable and functional.
With clients, I can either curate a signature piece if their style isn’t too developed or ask them if they have one that just captures them and can be the base that we build their style around. It’s not necessarily a piece one wears every day but has so the design elements to inspire what needs to be fleshed out more or what works on the person.
Lily is very unique, she has this air of softness to her, but she is sharp and I believe I have identified this piece captures this well for anyone wanting to get the look but may not have a good grasp on how to sport it because there is so much going on, but at the same time is so simple. In Blair Waldorf Must Pie, because we can’t do Gossip Girl without Thanksgiving Lily is known to really enjoy a well-executed Hermès moment, and here is one that honors her style which can be defined as elevated classic, but with a chic edge. This edge relates more ot her love of art and slightly rebellious side, yet overall she’s very refined.
For instance the Medor watch. It’s warm in tone, nicely crafted leather very classic, but then has these stark sudded adornments. Underneath the central stud is where the dial is concealed. Not the typical watch you’d think of, but then it is paired with a Kelly or Birkin. If you are intrigued by the significance of the Birkin bag, I previously have covered this on the channel but on the topic of Hermes, this is one of the brands that Lily wears the most. Hermès, as a fashion house, holds a conquest spirit with values of ingenuity, craftsmanship, quality, integrity, and independence that go into each piece. I feel this piece and brand captures Lily’s essence very well, keep this in mind throughout the analysis.
Additionally, Lily’s character is deeply concerned with appearances and image, often using fashion as a tool to project a certain persona or to navigate social situations between cashmere sweaters, warm wool jackets, structured carry-alls, and gowns befitting a gala. She wears flouncy blouses with military coats and ballet flats with denim. Her attention to detail and carefully curated outfits contribute to her cultivated image of sophistication and status. Refined is defined as elegant and cultured in appearance, manner, or taste but also developed or improved to be precise or subtle. That is where this very cultivated, polished appearance is formed and the process of her going from being a young girl getting kicked out of boarding school and setting off to Malibu, hanging out with her sister in the LA art scene to a gorgeous well put together woman everyone adores or respects,
Our clothing choices are a reflection of our individuality. Our personality traits, interests, values, and life experiences all influence the way we dress and the fashion preferences we develop. Although they have certain similarities, personality, and personal style are distinct aspects of an individual’s identity. What makes a person unique is their style, which is expressed via their clothing, accessories, personal hygiene habits, and overall appearance. Personality, on the other hand, is more of a broad category that encompasses an individual’s thoughts, feelings, behaviors, and interactions with others.
But having said that, there is a strong correlation between one’s personality and their style:
A person’s style is a window into their personality and sense of self. A person’s fundamental principles, interests, and beliefs can impact their choice of accessories and clothing. If you’re more reserved, opt for classic, understated designs; if you’re bold and adventurous, go for bold, colorful items.
Individuals with comparable personality qualities often maintain a constant personal style. Individuals with a conservative demeanor often choose a polished style, while those with a more adventurous and daring nature tend to prefer an eclectic or radical look. People’s responses to events are influenced by their cultural background, societal expectations, surroundings, and personal style, which are interconnected components of their identity. Someone with a reserved and professional demeanor may adapt their style to align with the expectations of their employer or the broader community.
Displaying confidence and showcasing one’s style is an effective method to reveal one’s identity to the world. When people dress in a way that mirrors their true selves, it may enhance their comfort and authenticity in social interactions. Studies indicate that a person’s fashion sense may impact their attitude, self-perception, and conduct. Expressing individual style via clothing may significantly boost self-esteem and contribute to general well-being. One’s demeanor in social settings might impact how others perceive and interpret their personality. People’s assumptions and evaluations of others are often influenced by their external looks and attire, even if they may not always accurately represent their genuine nature. One’s personality and personal style, while separate, are strongly linked since personal style visually represents one’s values, attributes, and self-perception.
Lily van der Woodsen has an ESFJ personality type, aka Extraverted, Sensing, Feeling, and Judging, which is is characterized by gaining from social interactions, possessing a practical and detail-oriented nature, making judgments guided by a rigid moral framework that tends to be uncompromising, and prioritize structure in order to maintain organization and productivity to meet goals, in Lily’s case this is financial and social. Lily strives more for a state of admiration, but more often than not she demonstrates a practical and grounded nature, paying attention to specific details in her personal and social life, such as fashion, decor, and etiquette.
Let’s break down how this functions regarding fashion. Lily is an extroverted person who loves to stand out from the crowd, and her dress choices are a reflection of that. Wearing clothes that make a statement and make her feel confident is a reflection of her outgoing attitude, which she uses to her advantage when she goes out socializing. She’s eye-catching, but doesn’t have a high degree of visual dominance like Serena who is the it girl everyone knows and loves.
More outgoing people tend to like the limelight and are comfortable drawing attention to themselves in social situations. To express themselves and draw attention to their outgoing attitude, they can dress in bold, vibrant colors. More extroverted people tend to dress in a way that reflects their sociability and communication style. Clothing with bold patterns, motifs, or logos may appeal to those who are energetic and full of life. Bold accessories that catch the eye and start conversations are a good choice for extroverts. They may express their outgoing and confident nature via their choice of footwear, which may include striking designs, unusual headpieces, or chunky jewelry.
More outgoing people tend to like trying new things and aren’t afraid to take style risks. They could be more brave to experiment with the latest trends and incorporate them into their own style. Most people who identify as extroverts are outgoing and like being around other people. This aspect of their personality may show through in the clothes they choose to wear to social gatherings, such as trendy party gowns or casual but stylish pieces for lounging about with friends. Extroverts are people who thrive in social situations, have excellent perception, and pay close attention to detail while dressing to make a statement. Improving their overall look may be as simple as coordinating accessories, as involved as layering garments, or as involved as paying close attention to grooming and detailing. The actions and personal style choices of extroverts are often characterized by an air of self-confidence. They dare to express themselves via the clothes they wear, uninhibited by societal norms and expectations.
I have analyzed her style as well as it girl look if you are interested in this, but Lily’s fashion choices often reflect her desire to make a statement and be noticed within her social circle or very similar to Blair actually to meet an objective. This usually is either romantic or professional, for instance, her look with Rufus is rather different than Bart’s, but in professional settings when she steps up she retains that classic signature look and uses her edge to her advantage. She enjoys attending social events and being seen, and her wardrobe reflects this extraverted aspect of her personality by incorporating pieces that capture attention and exude confidence. Confidence isn’t always loud, she’s rather tame.
Sensing (S): Lily’s style is based on real-life experiences and the here and now. She chooses well-made garments with tailored cuts and well-chosen accessories because she appreciates attention to detail. She has an innately pragmatic sense of style, prioritizing comfort and ease above fleeting fads.
Those who score high on the sensory dimension of the Myers-Briggs Type Indicator (MBTI) tend to be detail-oriented, pragmatic, and informationally biased. One way in which sensing people’s practicality and grounding show in their style is in their clothing choices. Comfort, durability, and functionality in their everyday attire may be more important to them than following the latest trends or showing off their sense of style. Traditionalists and stability seekers like sensing types tend to choose tried-and-true styles over fads that come and go. They could choose classic items like fitted blazers, clean button-down shirts, or adaptable denim jeans because of their simplicity and quality construction. People who possess good senses have an eye for detail and value physical attributes like how textiles feel. Their preference for long-lasting, comfortable textiles like cotton, wool, or leather suggests that they place a premium on material quality when shopping for apparel.
Fashion for Sensing Types: Understated and Subtle Rather Than Bold and Eye-Catching. Instead of wearing bright designs or eye-catching accessories, they could choose a more subdued style that is characterized by muted tones and neutral hues. Those who are sensitive to their surroundings are prone to value accessories for their practicality and usefulness. Some examples of functional items they could choose are a leather purse for daily usage or a pair of shoes that can withstand a variety of terrains. When it comes to business or formal situations, sensing types tend to dress conservatively because they cherish tradition. Opting for refined and subdued apparel, they are inclined to choose garments that conform to societal norms and dress rules. While intuitive people tend to go for more traditional looks, they do love a well-curated closet that has their unique accents. They could splurge on a well-tailored jacket in their go-to hue or a pair of shoes that are an ideal match for their active lifestyle—basic wardrobe essentials that show their sense of style.
We often see her in dresses and skirts, but at times a very simple blouse with denim. In terms of the style personalities, Lily is classic as the foundation and creative accessories with touches of elegance and feminine depending on what the occasion calls for from chic and sophisticated pieces like a silk scarf and structured bags to bows and pearls. For instance, she has this trademark slick low-back bun but at times maybe she does incorporate a braid or twist. Very subtle, but honors her signature while making her style adaptable. I believe a lot of people struggle with defining or establishing a personal style and then feeling boxed in, but this is a great example of how your style should make life more beautiful no matter what the occasion calls for it honors you, not the other way around.
When it comes to Lily’s style, her feelings and principles play a major role (F). Her clothes are a form of self-expression that she utilizes to show off her class, refinement, and social standing. She picks out items that speak to her sense of style and gives her a sense of self-assurance, so her wardrobe is a reflection of her quest for harmony and beauty. This requires her or well anyone to have trust in herself, such as her qualities and judgments.
In terms of judgment (J), Lily’s taste in clothing is defined by her love of neatness and orderly. She pays meticulous attention to detail and carefully plans her outfits, ensuring that every element complements each other. This style may be characterized by a love of classic pieces, impeccable tailoring, impeccable matching, meticulous organization of clothing, strict adherence to dress regulations, and self-assured fashion decisions. Those who lean toward judgment are known to be quite sure of themselves and their conclusions, even when it comes to their style. When it comes to choosing garments and accessories, they may be able to confidently express their style preferences. In settings with established dress requirements, the fashion choices of judging types could be impacted by the appreciation for explicit norms and regulations. Dressing by the established norms, they are likely to follow dress codes at work or for formal events. Some people have a methodical approach to organizing their closets, suggesting a preference for judgment. They could maintain a neat wardrobe, sorting garments by color, season, or event. This makes it easier for them to choose clothes that complement their style and work well for their everyday activities.
People with an udging personality type prefer to be organized and methodical, even when it comes to their clothing choices. They could lean toward well-planned ensembles in which every component serves to accentuate the others. This might be layering items deliberately, combining pieces, or wearing colors that complement one another. People who are good judges tend to choose more form-fitting styles and garments with sharp edges. Items like fitting blazers, clean button-down shirts, and pencil skirts could appeal to them because of the put-together vibe they give off. She never clashes, she relaxes in style, and even when ill she still is composed. Her wardrobe is curated with a sense of purpose, reflecting her refined taste and adherence to a certain aesthetic standard as well as the standard she holds herself to. We see her throw caution to the wind a bit with this in her romantic life as well as her family life, but to the outside world, she upkeeps this.
ESFJs excel as hosts and flourish in roles that allow them to assume responsibilities and provide support to their loved ones. Lily does all of this with elegance, finesse, and the offbeat scandalous story she will sweep under the rug or reminisce on with friends and family. During her adolescence, Lily had a rebellious lifestyle, fully engaging herself in the worlds of art and music, pursuing a passion in photography, and dating musician Rufus Humphrey. I loved the Valley Girls episode I really wish they had done the spin-off series, having that west coast charm with east coast sensibilities is beyond. I feel that anyone who watches that episode either loves it or hates it, I think it’s one of my favorite episodes I’d love to know your 2 cents on it. But getting back to the analysis, Lily from this point in her life underwent a shift
Lily underwent a shift in her mindset about her life’s values. So from this one episode, we get Lily on this quest of identity formation and developing a sense of direction. I’ve broken this down concerning personal style development with Jenny if you are interested in the psychological process of Erik Erikson’s theory of psychosocial development but if a person is unsure of their place in society, role confusion occurs. Lily initially has this very preppy look keeping in place her parent’s way of life, but in the locker there is a photo of Lily and Carol sneaking out to ice skate so even then we see she isn’t really this good girl everyone makes her out to be. We see her having fun with her sister, trying on trendy clothes, and her passion for the arts and music in her youth. We also know that Lily was pursuing photography at one point, but she turned away from this. We didn’t get the spin-off off so there is no set timeline, but I believe on the show notes it was with giving Scott for adoption and wanting security, placing more emphasis on social standing and financial freedom. I believe this makes a lot of sense. She still holds onto her passion for art and photography, but more to adorn her home and in the way she styles herself. I think the way Eric Damon styled her, is really beautiful because she isn’t this perfect character but this woman trying to navigate the world and of course, she begins to turn back to what her parents taught her, but also what she found in life to bring her joy or even security as a baseline.
We see this often in Lily’s color palette, she loves monochromatic ensembles and elevated neutrals such as dove grey and chocolate brown. Although neutrals can create a more classic European look, they do indicate a lack of enthusiasm, passion, and sentiment but are very timeless, versatile, and natural. This is because they are not located on the color wheel, but this makes those pops of colors stronger with a great visual impact. That contrast of a classic neutral tone or piece to a pop of color or abstract structure elevates the look nicely without overpowering her everyday looks, especially for events. We see a lot of texture play and embroideries which gives great dimension, really a nod to her character because many times classic style is very clean rather than intricate.
She has a great sense of fashion and always looks put together with unique composure, often enhancing her outfits with distinctive accessories like an avant-garde necklace or striking earrings. She regards fashion as an art form and acquires it in a similar way to how she would with her art dealer.
It reminds me so much of Kintsugi, meaning “join with gold.” If you don’t know or just need a little refresher, this is a Japanese technique for restoring broken ceramics, glass, and other pottery or porcelain goods. Placing broken pieces together with gold lacquer is a time-honored technique that transforms a piece broken beyond repair into a creation even more beautiful than before.
Lily’s style is all about bringing the pieces together, very similar to her nature, demeanor, or personality. Throughout the series, Lily navigates the complexities of Upper East Side society, balancing her social obligations with her desires, this balance is always present showing how important it is to embrace all sides of yourself and be unapologetically authentic. To not focus just on other opinions, but also on your desires and necessities in life.
