Podcast Episode Summary: "The Twitter Menswear Guy Takes Calls"

Podcast Information:

• Title: All Of It
• Host: Alison Stewart
• Description: ALL OF IT is a show about culture and its consumers, aiming to engage thinkers, doers, makers, and creators about the what and why of their work. The show builds a community around diverse perspectives, reflecting the vibrant culture of New York City.

Episode Details:

• Episode Title: The Twitter Menswear Guy Takes Calls
• Release Date: January 17, 2025
• Host: Alison Stewart
• Guest: Derek Guy, known as the "menswear guy," with over a million followers on Twitter for his comprehensive threads on men's fashion history.

1. Introduction to Derek Guy

[00:37] Alison Stewart: Welcomes Derek Guy, the "menswear guy" known for his detailed and informative threads on Twitter about men's fashion history. Derek has cultivated a substantial online following by addressing questions ranging from suit brands to jacket fit and the distinctions between suits and sports coats.

[01:08] Alison Stewart: Encourages listeners to call in with their menswear questions, setting the stage for an interactive and informative session.

2. Derek Guy’s Journey into Menswear

[01:46] Derek Guy: Shares his early interest in fashion, which was initially sparked not by clothing itself but by its role as a "subcultural uniform." He was deeply involved in the music and dance club scenes, where fashion served as a key identifier within various subcultures.

[02:25] Derek Guy: Discusses his personal heroes and influences in men's fashion, particularly those from the freestyle dance scene who wore brands like Polo Ralph Lauren. He delves into the origins of classic menswear staples like tweed jackets and chambray shirts, highlighting his journey of discovering the historical roots of these garments through menswear blogs and forums in the early 2000s.

3. Growth and Shift in Content Strategy

[03:29] Derek Guy: Explains a pivotal moment at the end of 2022 when his Twitter account surged from 50,000 to 100,000 followers. This spike was triggered by a viral thread critiquing Dave Portnoy’s Brick Watch and an ensuing discussion about the cashmere industry. Realizing that his audience preferred informative content over niche jokes, Derek shifted his focus to more substantial threads, resulting in continued growth and broader recognition, including features from major publications like the Washington Post.

4. Listener Q&A Sessions

A. Shopping on eBay and Thrift Tips

[05:15] Reid from Brooklyn: Asks for recommendations on shopping for vintage menswear on eBay, specifically sweaters and pants.

[05:56] Derek Guy: Provides detailed advice on finding quality sweaters, emphasizing that country of origin is no longer a definitive indicator of quality. He suggests searching for specific fibers like cashmere or Shetland wool and filtering results by regions known for quality knitwear, such as Scotland. Derek also advises checking measurements meticulously to ensure proper fit when purchasing online.

“An easy way to find a good sweater is to search for the fiber you’re looking for, like cashmere or lambswool, and then include the country of origin, such as Scotland, to filter high-quality options.” [06:16]

B. Surgeon Cuffs on Suits

[08:36] Listener via Instagram: Inquires about the discontinuation of surgeon cuffs on blazers and suits, wondering why designers have moved away from them.

[08:48] Derek Guy: Argues that surgeon cuffs haven't disappeared but are often misapplied in ready-to-wear suits to signify quality. He explains the historical purpose of surgeon cuffs and critiques their use in modern ready-made garments, advocating instead for unfinished cuffs that allow for alterations without compromising the garment's functionality.

“Designers actually started using surgeon cuffs because consumers associate them with quality, but for ready-to-wear suits, unfinished cuffs are preferable as they allow for adjustments.” [08:48]

C. Menswear as a Language

[10:23] Alison Stewart: Highlights a listener's testimonial about relying on Derek's advice for wedding suit shopping and poses a question about high-end pre-owned suits versus less expensive off-the-rack options.

[10:34] Derek Guy: Compares menswear to a cultural language, emphasizing that dressing is a form of self-expression and group identification rather than merely following trends. He suggests adopting an aesthetic inspired by cultural sublanguages to create coherent and personal style statements.

“Clothing is a form of social language, a way to identify with a group and express yourself as an individual within that group.” [10:34]

D. Buying Pre-Owned Suits

[12:23] Derek Guy: Advises that pre-owned suits can be a viable option, especially when purchased in person, to ensure proper fit and quality. He recommends seeking out donations from affluent neighborhoods or charity shops associated with high-quality organizations for better selections. For online purchases, he stresses the importance of verifying measurements and ensuring easy returns.

“It is better to shop in person at a secondhand store to ensure the suit fits well, especially since suits are less forgiving than other garments.” [12:23]

E. Styling Jeans with Shoes

[14:56] Reed from Forest Hills: Asks for advice on pairing jeans with shoes and selecting appropriate cuts and styles for everyday casual wear.

[15:10] Derek Guy: Recommends a slimish straight leg cut, such as Levi's 501 Vintage Fit or similar styles from brands like Gustin. For shirts, he suggests opting for casual button-ups like plaid flannels or textured oxford shirts to complement the jeans. Regarding footwear, he advises choosing versatile options like Chukka boots, sneakers, or penny loafers, avoiding overly dressy shoes like Oxfords for casual outfits.

“Think of your ensemble as a cohesive unit where formality and style harmonize; this approach simplifies decisions about fit, color, and footwear.” [15:10]

F. Suit Vest Button Rules

[15:56] Mike from Bed Stuy: Inquires about the etiquette of leaving the bottom button of a suit vest unbuttoned.

[15:42] Derek Guy: Confirms that traditionally, the bottom button of a vest should remain unfastened. He explains the historical origin of this rule and notes that while some modern vest cuts may not allow buttoning the last button without affecting the jacket's fit, the general guideline remains to leave it open to maintain a polished appearance.

“Generally speaking, the bottom most buttons should not be fastened, adhering to the classic rule to maintain the vest’s proportion and functionality.” [15:42]

G. Suits for Larger Frames

[19:42] Mike: Seeks advice for taller and larger individuals (6’7”) on selecting suits without relying solely on custom tailoring.

[20:13] Derek Guy: Acknowledges the challenges faced by larger individuals in finding well-fitting suits due to the decline of the tailoring industry. He suggests seeking out specialized stores like O'Connell’s in Buffalo, New York, which offer larger sizes and custom paper patterns. Derek emphasizes the importance of focusing on fit specifics, such as shoulder alignment and jacket length, and recommends shopping in person when possible to ensure garments accommodate unique body dimensions.

“The most important thing is the fit of the shoulders and ensuring you can move comfortably without the suit feeling restrictive or ill-fitting.” [20:13]

H. Color Coordination: Black with Blue

[22:35] Derek Guy: Discusses the appropriateness of pairing black with blue, asserting that it depends heavily on context. He distinguishes between formal combinations, like black ties with navy suits, and less traditional pairings, such as navy shoes with black suits, which he considers unconventional and stylistically inconsistent.

“A black silk tie looks fantastic with a navy suit, but navy shoes with a black suit don’t align with traditional styling norms.” [22:35]

I. Suit Pants and Ankle Length

[23:34] Listener Inquiry: Requests advice on the ideal length of suit pants—whether they should cover the shoe or show the ankle.

[23:51] Derek Guy: Advises adhering to classic guidelines: trousers should either have a slight break where the hem touches the top of the shoe or have one subtle break. He emphasizes consistency with the shoes worn during hemming and suggests that any deviations, like cropped or stacked pants, should align with a deliberate aesthetic choice rather than casual experimentation.

“The pant should either have a shivering break or one break, maintaining a straight line from hips to shoes for a classic and versatile look.” [23:51]

J. Fashion Pet Peeves

[25:14] Derek Guy: Expresses his disdain for "dress sneakers," which he considers aesthetically compromised. He explains that these hybrid shoes fail to fit seamlessly with either formal or casual outfits, recommending instead the use of distinct dress shoes and casual sneakers to maintain clarity and cohesiveness in one’s wardrobe.

“Dress sneakers look like a midway point between dress shoes and casual sneakers, failing to work well with either formal or casual ensembles.” [25:14]

5. Conclusion

[26:04] Alison Stewart: Wraps up the interview by thanking Derek Guy for his insights and contributions as the "menswear guy" behind Dye Workwear and his influential presence on social media.

[26:16] Derek Guy: Thanks Alison Stewart for the opportunity to share his expertise.

Notable Highlights and Insights

• Cultural Language of Fashion: Derek emphasizes that fashion serves as a form of social language, enabling both individual expression and group identification.

• Evolving Menswear Trends: He highlights the shift from niche, humor-based content to more informative and educational threads that resonate with a broader audience.

• Practical Fashion Advice: From sourcing quality garments online to understanding the nuanced rules of suit styling, Derek provides actionable tips for listeners to enhance their personal style.

• Industry Challenges: Addresses the declining availability of custom tailoring and offers solutions for individuals with unique sizing requirements.

• Aesthetic Consistency: Stresses the importance of maintaining coherence in outfit formality and style to achieve a polished and intentional look.

Quotes with Timestamps

1. “An easy way to find a good sweater is to search for the fiber you’re looking for, like cashmere or lambswool, and then include the country of origin, such as Scotland, to filter high-quality options.” [06:16]

2. “Clothing is a form of social language, a way to identify with a group and express yourself as an individual within that group.” [10:34]

3. “Generally speaking, the bottom most buttons should not be fastened, adhering to the classic rule to maintain the vest’s proportion and functionality.” [15:42]

4. “A black silk tie looks fantastic with a navy suit, but navy shoes with a black suit don’t align with traditional styling norms.” [22:35]

5. “Dress sneakers look like a midway point between dress shoes and casual sneakers, failing to work well with either formal or casual ensembles.” [25:14]

Final Thoughts: In this episode of All Of It, Derek Guy offers a wealth of knowledge on men's fashion, blending historical context with practical advice. His ability to demystify complex fashion concepts and address listener inquiries underscores his role as a trusted authority in the menswear community. Whether discussing the origins of classic garments or navigating the challenges of finding well-fitting suits, Derek provides valuable insights that empower listeners to cultivate their personal style with confidence and understanding.