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derek guy @dieworkwear.bsky.social · Apr 5

Gitman's oxford button-down shirts, made in the USA

December 2024: $205
April 2025: $235

A screenshot from Internet Archive, which shows what Gitman's website looked like on December 11, 2024. The product page for Gitman's Blue Oxford shirts shows a price of $205.

The same page on April 5, 2025 shows the same product being sold for $235. Nothing else about the shirt has changed.

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derek guy @dieworkwear.bsky.social · Feb 16

If your aesthetic is driven by homophobia, you'll always be chasing the latest code, unaware of how those styles landed in your wardrobe. Instead, I encourage you take inspiration from all of culture, including menswear and womenswear, and create an aesthetic that expresses you.

A screenshot of the original Twitter poster who wrote: "Wearing women’s clothes has never been in style, homo"

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derek guy @dieworkwear.bsky.social · Feb 16

Some men can wear dainty items like Belgian loafers—which feature a little bow—and look *more* masculine. Others can wear the same item and look a bit feminine. How gender is expressed through style is complex. It's not just about the item; it's also about body and personality.

A man wears black suede Belgian loafers with a blue denim trucker jacket and blue flared jeans.

A man wears brown suede Belgian loafers with a blue kurta and patched-up tan chinos.

A man wears suede leopard patterned Belgian loafers with a black graphic t-shirt and blue jeans.

A man wears black suede Belgian loafers with a black velvet blazer, blue turtleneck, and grey houndstooth trousers. He also has big sunglasses with yellow tinted lenses.

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derek guy @dieworkwear.bsky.social · Feb 16

Few people fit these cartoonish binary representations of gender—most people are on the gender spectrum. The issue of "men in womenswear" is less about thinking of which styles are "legitimate vs taboo," but rather considering how style can be expressed.

Lenny Kravitz wearing flared blue jeans, a leopard print top, big sunglasses, and a black silk neckerchief.

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derek guy @dieworkwear.bsky.social · Feb 16

In 1973, feminist scholar Carolyn G. Heilbrun wrote an article for the New York Times titled "Androgynous World," which encouraged readers to think of gender as a spectrum. "[B]etween the quarterback and the cheerleader, we have lost too much of our humanity," she cautioned.

A screenshot from the New York Times article. It reads:

"For the hostile, who in some sense feel threatened by this unfamiliar idea, further assurance is required. Androgyny does not mean the loss of all distinctions; those who are terrified by the word probably envision everyone, man and woman, dressed indistinguishably, like members of the Chinese Army. Those who are terrified further assume that in robbing us of clearly delineated sexual models, androgyny will rob us of all order and sanity. If we are to have more than two accepted role models—in youth, the quarterback and the cheerleader, in later life, the corporation manager and the corporation manager's wife—will we not in fact be diving off the edge of an ordered world into the abyss?

To which one must answer: between the quarterback and the cheerleader, we have lost too much of our humanity; we have come close to losing humanity altogether. What is more, the possibilities for companionship between men and women can only be heightened by androgynous energy. For androgyny implies not only that couples may find or create their own pattern of passion or conversation, but that marriage may become joyful for those who are neither quarters backs nor cheerleaders and do not now wish to play those roles."

A screenshot from the same article. It reads:

"The received ideas of masculine and feminine have operated in three destructive ways. First, by insisting on the masculinity of men and the femininity of women, we have locked individuals into prisons of gender, where their response is likely to be either a mindless acquiescence, or violence and rebellion. Second, the overly defined distinction between the received ideas of masculinity and femininity has brought about a sexual polarization in our society that deprives both men and women of their common humanity in relation to one another, and has separated what should have been joined. Third, by placing in power those men at the most “masculine” end of the spectrum of human possibility, we have endangered our own survival. My hope for the idea of androgyny is that it will not become another fad, briefly puffed up by the media, but soon mentioned only to groans of boredom. That is the danger. But if, as I believe, the androgynous ideal reaches back into the very roots of our literature, religions and ancient wisdom, it will prevail. Present at the birth of every religion, submerged or subverted in most religions thereafter, androgyny hints at a new equilibrium in an unbalanced world. Those who are unmoved by an appeal to humanity's mythic origins might reflect upon the undeniable impact of modern technology, which has freed the sexes from biologically differentiated social and economic roles and from the behavioral patterns traditionally associated with them."

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derek guy @dieworkwear.bsky.social · Feb 16

There's nothing inherently feminine about Kendrick's jeans (IMO, the longer length suits the style of the outfit). It's true that Hedi Slimane, who designed these Celine jeans, said he originally made them for women. But then he said they're unisex. So now what?

Kendrick Lamar wearing flared Celine jeans at the Super Bowl.

A screenshot from Hedi Slimane's Instagram. He writes:

"KENDRICK LAMAR’S HEDI SLIMANE FLARED JEANS FOR CELINE . THE SUPER BOWL 2025.

In his Spring/Summer 2020 collection for Celine, Hedi Slimane, who launched the skinny jeans in the late 90’s at YSL and Dior Homme, introduced his first flared jeans as a tribute to Serge Gainsbourg. These jeans were showcased during his Celine fashion show on June 23, 2019.

Hedi Slimane’s “Serge” flared jeans were succeeded by the “Marco” flared jeans, which he initially designed for women for the Bibliothèque Nationale show. However, Slimane’s creations are inherently unisex, reflecting a design philosophy that transcends traditional gender boundaries.

Kendrick Lamar donned Hedi Slimane’s flared jeans for Celine during his performance at the Super Bowl 2025 Halftime Show, highlighting the enduring influence of Slimane’s designs."

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derek guy @dieworkwear.bsky.social · Feb 16

It's difficult to address the original poster's criticism because the very *coding* of clothing can change over time. Flares were originally worn by sailors and cowboys, then Coco Chanel, and then hippies. The codes can change depending on who's wearing something.

Two images of sailors and cowboys wearing flared pants.

Coco Chanel on the beach wearing flared pants.

1970s hippies wearing flared pants. There appears to be men and women in the photo, although the image only shows the people from the waist down.

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derek guy @dieworkwear.bsky.social · Feb 16

Take a closer look at male politicians next time they appear in photos or on television. Many are wearing make-up. I'm not talking about just powder, which is sensibly used to make skin look matte under bright lights, but beautifying products like blush, bronzer, and concealer.

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derek guy @dieworkwear.bsky.social · Feb 16

In the last 30 years, skinny jeans have moved from "womenswear" to "androgynous" to "hip guy" to "passé." As I've said, it's ironic that some of the most critical voices in today's gender wars are wearing a cut that was once seen as a sign of declining masculinity in the West.

Matt Gaetz at the Barbie premiere. He's wearing a pink sport coat with black skinny jeans and black monk-strap shoes.

Matt Walsh at the premiere of "What is a Woman?" He's wearing a small blue sport coat, grey t-shirt, black skinny jeans, and tan derbies.

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derek guy @dieworkwear.bsky.social · Feb 16

This silhouette was then made desirable through bands such as The Strokes and non-gender-conforming hipsters. Men who couldn't afford Dior jeans raided the women's aisle for their denim—a move Levi's celebrated in 2011 when they released their "ex-girlfriend cut" for men.

Members of the band The Strokes. Two of the members are wearing skinny jeans with low-cut v-neck t-shirts.

A screenshot of the Levi's website. The product page shows the "Ex-Girlfriend Jean" in black.

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derek guy @dieworkwear.bsky.social · Feb 16

Back when he was the creative head of Dior, Hedi Slimane made waves by releasing skinny jeans for men, which he later said was an intentional celebration of androgyny, as that type of cut was only worn by women at the time.

A photo of a man during a Dior runway show and a woman on the street. Both are wearing skinny, low rise jeans.

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derek guy @dieworkwear.bsky.social · Feb 16

"But Derek," you protest, "these are pretty niche. Surely normal guys were never wearing womenswear."

Not true. We first have to again recognize that codes change over time. For instance, the slim fit trend today started with non-conforming men.

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derek guy @dieworkwear.bsky.social · Feb 16

Radical drag never took off because ... well, it was too radical for the mainstream. But it did influence protopunk bands such as The New York Dolls, who performed in feminine dresses, long hair, and glitter-glam make-up. And they influenced the glam rock bands of the 1980s.

Members of the New York Dolls in tight pants, big hairstyles, and make-up.

Members of Motley Crue in similar attire at the New York Dolls.

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derek guy @dieworkwear.bsky.social · Feb 16

Taking inspiration from transgender sex workers, many gay men adopted "radical drag," which blurred gender lines by combining extreme symbols of masculinity and femininity. Gold lamé dresses were worn with work boots; pink tutus were paired with Army jackets.

Some men in what appears to be a 1970s photo wearing womenswear. They are strolling down the street.

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derek guy @dieworkwear.bsky.social · Feb 16

IMO, real fashion is not about celebrities—it's about what happens on the ground. One of the most important moments of "men in womenswear" happened in the wake of the Stonewall Riots, which made many gay men tired of hiding in the closet.

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derek guy @dieworkwear.bsky.social · Feb 16

In more recent memory, Kanye wore a Celine blouse at 2011 Coachella. I can tell you that this was widely celebrated and seen as stylish among people interested in menswear. Even Travis Scott later copied the look.

Kanye West at the 2011 Coachella. He's standing in front of a mic while while wearing a silky Celine blouse in pink, blue, green, and cream. He's also wearing slim jeans and gold chains. The blouse is barely buttoned, so much of his chest is showing.

Travis Scott in a nearly identical outfit, except he has a white t-shirt underneath the Celine blouse. He's also wearing a diamond studded Cuban link chain, rather than just a bunch of gold chains like Kanye.

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derek guy @dieworkwear.bsky.social · Feb 16

Similarly, Prince was known for his ruffled shirts and dramatic lace outfits. He reportedly had over 3,000 pairs of bespoke shoes. These fantastical, steel-bar-reinforced booties were made with glimmering studs, custom zipper pulls, and embroideries.

Prince in a double-breasted suit and small booties.

A pair of Prince's booties. They are made from green textured material in a pattern that mimics leaves.

A white pair of Prince's booties. The heels are studded.

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derek guy @dieworkwear.bsky.social · Feb 16

But there are plenty of male style icons who wore women's clothing. David Bowie, particularly during his Ziggy Stardust era, blurred gender lines by wearing women's blouses, jumpsuits and high-heeled boots.

David Bowie with red hair, red lipstick, make-up, and some kind of shiny, quilted black top.

David Bowie pushing a stroller while wearing a blouse, floppy hat, and very wide legged pants.

David Bowie wearing a blue boa scarf and a knitted garment (perhaps a dress?) along with matching knitted sleeves.

David Bowie in a white jumpsuit and high-heeled shoes.

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derek guy @dieworkwear.bsky.social · Feb 16

Plenty of things started on the womenswear side of the aisle before crossing over into men's. Prior to the 20th century, men carried pocket watches and only women wore wristwatches. The humble t-shirt began as the top of union suits, which was once considered women's underwear.

An illustration of some men surrounding Queen Elizabeth. One appears to be adjusting her watch. The caption reads: For Queen Elizabeth was made the first wrist watch.

An old newspaper ad for women's union suits. There are three illustrations of a woman. She's wearing a union suit, which is a one-piece garment worn as underwear. There's a bit of lace at the top.

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derek guy @dieworkwear.bsky.social · Feb 16

We should first recognize that gender codes are socially constructed. Clothing is not inherently masculine or feminine—codes are contextual and can change over time. Aristocratic men once wore bright red heels. Then they became womenswear until that notion was challenged again.

A painting of King Louis XIV of France. He's wearing an opulent outfit made of furs, lace, and gold. He's also wearing white buckled shoes with a high red heel.

A close-up of the white buckled shoes with a high-red heel. There appears to be a red lace at the top of the shoes.

Fashion influencer Luka Sabbat wearing a black leather suit and black boots with a very high heel.

James Baldwin wearing a white, short-sleeved button-down shirt, white cotton pants, and brown Cuban heeled side-zip boots. He also has chunky gold and turquoise jewelry (bracelet and ring).

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derek guy @dieworkwear.bsky.social · Feb 16

Not true. I'll give you some examples of when styles crossed over from womenswear to menswear, and how men have worn straight-up womenswear or just feminine styles in cool ways. 🧵

A screenshot from Twitter.

The original tweet reads: "Rapper Kenderick Lamar wore size 29 women's jeans to Super Bowl LIX." The tweet garnered over a thousand replies, most negative.

I (Derek Guy) screenshotted that tweet and wrote: "so funny to see history repeat itself. men who wear slim fit and stretch denim—both of which were once considered strictly for women—criticizing kendrick for wearing flares bc they were on the women's aisle. in ten years, you'll be in flares clutching pearls about something else"

Then another user replied to my tweet, saying: "Wearing women’s clothes has never been in style, homo."

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derek guy @dieworkwear.bsky.social · Feb 20

I've been writing a series of essays for PBS on men whose style I admire. The latest is about James Baldwin, a man who knew how to sing through clothes.

www.pbs.org/wnet/america...

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derek guy @dieworkwear.bsky.social · Feb 21

men who dressed like this from 2008 - 2012 had preppy menswear blogs

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derek guy @dieworkwear.bsky.social · Feb 25

Joann had a sprawling retail footprint and was a victim of the slow US decline toward cheaper, more disposable clothing, but they also suffered a blow during Trump's first term. Trump's 2018 tariffs increased cost of imports and US equivalents were too expensive for customers.

Headline from The New York Times: "Joann, 80-Year-Old Crafts and Fabrics Retailer, Will Close All Stores. The announcement that the chain would close all 800 of its stores in 49 states comes after a period of financial turmoil."

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derek guy @dieworkwear.bsky.social · Mar 1

american masculinity is so amazing. caring about clothes as a man apparently makes you "gay" but our position on geopolitics totally depends on whether you wear a suit

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