Lessons from Derek Guy

As a prominent voice in menswear, Derek Guy, the writer behind "Die, Workwear!" and an editor at "Put This On," has become a go-to source for advice on style, quality, and the cultural significance of clothing. [1][2] Through his prolific writing and social media presence, he has shared countless insights that have helped men navigate the often-confusing world of fashion.

On Personal Style and Authenticity

Fashion as a Language: "I've always thought of fashion as a kind of cultural and social language. People dress in ways to express themselves—their culture, background, identity, and sometimes even aspirations." [1] (Source: Sanpetuna, https://sanpetuna.com/blogs/news/interview-with-derek-guy)
Dressing for Yourself: On the tradition of "Formal Friday" with his wife, even if they are more dressed up than others: "We dress for ourselves and each other, and that's it. We have reached a point in our lives where it is time to be ourselves." [3] (Source: Mr Porter, https://www.mrporter.com/en-gb/journal/fashion/dieworkwear-how-to-wear-more-tailoring-24513634)
Embrace Variety in Your Wardrobe: "A singular, narrow wardrobe will never reflect the complexity of everything you're about." [4] (Source: Put This On, https://putthison.com/get-you-a-man-who-can-do-both/)
Authenticity in Diverse Styles: When asked if it's possible to wear disparate styles and still be authentic, he suggests that dressing for how you feel each day is a better reflection of your personality than adhering to a strict uniform. [4] (Source: Put This On, https://putthison.com/get-you-a-man-who-can-do-both/)
Don't Be Afraid to "Play Dress Up": The idea that men's dress was historically governed by time, place, and occasion is a relatively recent concept. It's okay to experiment with different aesthetics. [4] (Source: Put This On, https://putthison.com/get-you-a-man-who-can-do-both/)
Style and Persona: "Some people feel that you should dress not only for your body type, but also for a persona. In other words, your clothes should be a reflection of your personality, interests, and background." [4] (Source: Put This On, https://putthison.com/get-you-a-man-who-can-do-both/)
The Joy of Dressing Up: Encourages finding occasions to dress up, like a weekly dinner with friends, to have something to look forward to and an excuse to wear tailoring. [3] (Source: Mr Porter, https://www.mrporter.com/en-gb/journal/fashion/dieworkwear-how-to-wear-more-tailoring-24513634)
Clothing Communicates: Guy maintains that the clothes we wear are shaped by politics, economics, and culture, and they still hold meaning today. [5] (Source: YouTube, https://www.youtube.com/watch?v=8qq5vQIv7V4)

On Quality and Value

The Cost-Per-Wear Principle: He emphasizes that the value of a garment comes from how often you wear it. An expensive item worn daily can be a better investment than a cheap, rarely worn one. [6] (Source: Reddit, https://www.reddit.com/r/malefashionadvice/comments/160vvr6/advice_on_building_a_wardrobe_from_derek_guy/)
Good Clothes Aren't Cheap, and Cheap Clothes Aren't Good: A succinct summary of his philosophy on investing in quality garments. [7] (Source: Boss Hunting, https://www.bosshunting.com.au/style/derek-guy-interview/)
The Peril of "Good Enough" on Sale: "The only things you should buy on sale are things you already wanted to buy when they weren't on sale." [6] (Source: Reddit, https://www.reddit.com/r/malefashionadvice/comments/160vvr6/advice_on_building_a_wardrobe_from_derek_guy/)
Starting Out with Cheaper Items is Okay: When you're beginning to build a wardrobe, it's acceptable to buy less expensive pieces because your taste is still developing. [6] (Source: Reddit, https://www.reddit.com/r/malefashionadvice/comments/160vvr6/advice_on_building_a_wardrobe_from_derek_guy/)
Accessibility Without Exploitation: "The industry needs to find a way to make quality more accessible without exploiting workers or the planet." [7] (Source: Boss Hunting, https://www.bosshunting.com.au/style/derek-guy-interview/)

On Tailoring and Fit

The Unforgivable Crime: He is known for his strong stance against putting rubber sneaker soles on a dress shoe. [2] (Source: Glossy, https://www.glossy.co/fashion/glossy-storytellers-2024-derek-guy-die-workwear/)
Shorter Jackets and Body Proportions: "Shorter jackets make you look heavier than you are, which means they're only ever good on stick-thin models whose shoulders are broader than their hips." [8] (Source: Ask Andy About Clothes, https://www.askandyaboutclothes.com/threads/words-of-wisdom-from-derek-guy-of-die-workwear.233784/)
The Benefit of Drape: "If you have a less-than-athletic figure, you may benefit from having a little extra room in the shoulders and chest." [8] (Source: Ask Andy About Clothes, https://www.askandyaboutclothes.com/threads/words-of-wisdom-from-derek-guy-of-die-workwear.233784/)
Incorporating Tailoring Gradually: If a full suit feels like too much, start by wearing a sport coat with a button-down shirt and chinos or even jeans. [3] (Source: Mr Porter, https://www.mrporter.com/en-gb/journal/fashion/dieworkwear-how-to-wear-more-tailoring-24513634)
Casual Tailoring: A suit can be dressed down with a denim western shirt, or a sport coat can be paired with a cashmere sweater for a more relaxed but still put-together look. [3] (Source: Mr Porter, https://www.mrporter.com/en-gb/journal/fashion/dieworkwear-how-to-wear-more-tailoring-24513634)
The Power of a T-shirt with a Suit: A plain white tee made from fine cotton can be a stylish way to dress down a suit. [3] (Source: Mr Porter, https://www.mrporter.com/en-gb/journal/fashion/dieworkwear-how-to-wear-more-tailoring-24513634)
Understanding the Nuances of "Bespoke": Guy is known for his detailed explanations of the differences between bespoke, made-to-measure, and off-the-rack tailoring. [7] (Source: Boss Hunting, https://www.bosshunting.com.au/style/derek-guy-interview/)
Dressing for Larger Figures: He has provided advice on how to dress well for larger male figures, focusing on flattering silhouettes and proportions. [9] (Source: Reddit, https://www.reddit.com/r/malefashionadvice/comments/10g9ahc/dressing_for_larger_male_figures_from_derek_guy/)
Giorgio Armani's Influence: He has written about how Giorgio Armani "tore the stuffing out of suits" and focused on silhouette, drape, and proportion to create a "soulful, sophisticated simplicity." [10][11] (Source: Muck Rack, https://muckrack.com/derek-guy, https://muckrack.com/derek-guy/articles)

On Menswear Culture and Community

Making Menswear Accessible: "We need to make menswear accessible so that people who may have never thought about dressing better can find joy in clothes." [1] (Source: Sanpetuna, https://sanpetuna.com/blogs/news/interview-with-derek-guy)
The Importance of Entry Points: Basic items like oxford cloth button-downs can be a gateway for people to develop a deeper interest in clothing. [1] (Source: Sanpetuna, https://sanpetuna.com/blogs/news/interview-with-derek-guy)
Connecting Clothing to Broader Stories: "I try to connect clothing to some broader story about history, sociology, or politics—things people care about—which I think then makes clothing feel more relevant to their lives." [1] (Source: Sanpetuna, https://sanpetuna.com/blogs/news/interview-with-derek-guy)
The Hobbyist Community: He became involved in menswear through online forums and blogs in the early 2000s, highlighting the importance of community in developing style. [12] (Source: YouTube, https://www.youtube.com/watch?v=uAKMolRKphE)
Influence of Music on Style: His initial interest in clothing was sparked by the music scene and how dancers and musicians dressed. [5] (Source: YouTube, https://www.youtube.com/watch?v=8qq5vQIv7V4)
Highlighting Under-Appreciated Designers: He uses his platform to praise and bring attention to up-and-coming and lesser-known designers and brands. [2] (Source: Glossy, https://www.glossy.co/fashion/glossy-storytellers-2024-derek-guy-die-workwear/)
The "Springboard Wardrobe": A concept he has written about to help men build a foundational and versatile wardrobe. [6] (Source: Reddit, https://www.reddit.com/r/malefashionadvice/comments/160vvr6/advice_on_building_a_wardrobe_from_derek_guy/)
Critique as Education: His detailed critiques of outfits, often of public figures, serve as educational threads on the principles of good dressing. [2] (Source: Glossy, https://www.glossy.co/fashion/glossy-storytellers-2024-derek-guy-die-workwear/)
The Frivolity Myth: He challenges the Western societal view that fashion is frivolous, arguing that it's deeply intertwined with significant aspects of human life. [12] (Source: YouTube, https://www.youtube.com/watch?v=uAKMolRKphE)
Everyone Cares About Clothing to Some Degree: Even those who claim not to care about clothes make choices based on social cues and what their attire communicates. [12] (Source: YouTube, https://www.youtube.com/watch?v=uAKMolRKphE)
The Politics of Dress: He often discusses how clothing is tied to political expression and identity. [12] (Source: YouTube, https://www.youtube.com/watch?v=uAKMolRKphE)
Asian Calling About Bespoke: A witty retort to a detractor, showcasing his humor and expertise. [7] (Source: Boss Hunting, https://www.bosshunting.com.au/style/derek-guy-interview/)
The Lo Life Subculture's Influence: His interest in fashion was partly shaped by the Lo Life subculture's appreciation for Polo Ralph Lauren. [13] (Source: Wikipedia, https://en.wikipedia.org/wiki/Derek_Guy)
Fashion and Identity: "Fashion could play a role in this by fostering a sense of place and identity." [7] (Source: Boss Hunting, https://www.bosshunting.com.au/style/derek-guy-interview/)
The Evolution of His Content: As his audience grew, he shifted from niche jokes to more broadly useful advice, like how to buy a quality cashmere sweater. [1] (Source: Sanpetuna, https://sanpetuna.com/blogs/news/interview-with-derek-guy)
The Story of Fashion is Not Trivial: He argues against the idea that fashion is just a series of meaningless, fleeting trends. [12] (Source: YouTube, https://www.youtube.com/watch?v=uAKMolRKphE)
Well-Rounded Dressers are Rare: He notes that it's uncommon for someone who excels at casualwear to also be adept at wearing tailored clothing, and vice versa. [4] (Source: Put This On, https://putthison.com/get-you-a-man-who-can-do-both/)
His Writing and Other Ventures: Besides his blog and social media, he is a regular columnist for Mr Porter and has written for numerous other prestigious publications. [2] (Source: Glossy, https://www.glossy.co/fashion/glossy-storytellers-2024-derek-guy-die-workwear/)
European Brand Alternatives: While he often recommends American brands, there are European equivalents for those seeking similar quality and style. [14] (Source: Reddit, https://www.reddit.com/r/malefashionadvice/comments/1fkhjbf/alternative_derek_guy_guide_for_europeans/)
The Business Suit as a Default: He observes that even in an increasingly casual world, the business suit remains the standard for politicians and on solemn occasions. [5] (Source: YouTube, https://www.youtube.com/watch?v=8qq5vQIv7V4)
The Historical Context of the Suit: He connects the rise and fall of the suit to the birth of political liberalism. [5] (Source: YouTube, https://www.youtube.com/watch?v=8qq5vQIv7V4)
On Being "Weird": He has reflected on being called "weird" for his deep interest in clothing, a label he has come to terms with. [7] (Source: Boss Hunting, https://www.bosshunting.com.au/style/derek-guy-interview/)
Frugality Outside of Clothing: Despite his focus on high-quality clothing, he describes himself as a "fairly frugal person" in other aspects of his life. [7] (Source: Boss Hunting, https://www.bosshunting.com.au/style/derek-guy-interview/)
Shopping Secondhand: Through his work on "Put This On," he encourages shopping on eBay and other secondhand platforms. [11] (Source: Muck Rack, https://muckrack.com/derek-guy/articles)
The Appeal of a Uniform: He acknowledges the appeal of having a personal uniform for its simplicity and consistency. [4] (Source: Put This On, https://putthison.com/get-you-a-man-who-can-do-both/)
The Power of Variety: A diverse wardrobe allows you to dress appropriately for any situation and to experiment with color, texture, and silhouette. [4] (Source: Put This On, https://putthison.com/get-you-a-man-who-can-do-both/)
His Beginnings as a Writer: He started his blog in 2011 and also wrote for "Put This On," building his reputation over many years. [12][13] (Source: Wikipedia, https://en.wikipedia.org/wiki/Derek_Guy; YouTube, https://www.youtube.com/watch?v=uAKMolRKphE)
Clothing and Human Stories: "If you tell any story that involves humans, there will be clothing involved because humans wear clothes." [1] (Source: Sanpetuna, https://sanpetuna.com/blogs/news/interview-with-derek-guy)

Learn more:

Lessons from Derek Guy

On Personal Style and Authenticity

On Quality and Value

On Tailoring and Fit

On Menswear Culture and Community

Written by Antoine Buteau

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