Hugo Ferdinand Boss started small. Born in 1885 in Metzingen, Germany, he launched his clothing company in 1924, stitching workwear in a struggling economy. By 1931, with the Great Depression biting hard, Boss joined the Nazi Party—not just for the ideology, but for survival. Historian Roman Köster, in a 2011 company-funded study, notes Boss was a believer in National Socialism, but party membership also meant contracts. Big ones. From 1933, his factory cranked out brown SA shirts, Hitler Youth outfits, and those infamous SS uniforms, boosting sales from 38,260 Reichsmarks in 1932 to over 3.3 million by 1941.

Here’s the catch: Hugo Boss didn’t design the SS uniforms. That was Karl Diebitsch, an SS officer and artist, with help from Walter Heck in 1932. Boss was just a manufacturer, following orders to produce the stark, militaristic gear that became a symbol of terror. Still, being a cog in the Nazi machine doesn’t exactly make you innocent.

When the Third Reich fell in 1945, Boss faced denazification. Labeled a Nazi “activist, supporter, and beneficiary,” he was fined 100,000 Reichsmarks (later reduced) and banned from business. He claimed he only joined the party to save his company, and by 1948, when he died, he’d been downgraded to a “follower.” The company, though, kept going. Under new management—his son-in-law and nephews—Hugo Boss pivoted to men’s luxury suits by the 1960s, hitting its stride in the ‘70s with stars like Sylvester Stallone rocking the brand.

The Nazi past stayed buried until the ‘90s when lawsuits and a Swiss bank account scandal forced Hugo Boss to confront its history. The company issued an apology in 2011, expressing regret for its role under the Nazis. On X, though, the stigma lingers—users still call it “Hitler’s tailor,” and fake 1930s ads (debunked as Photoshop jobs) keep the myth alive.

Coco Chanel – the iconic French fashion designer, was involved with the Nazis during World War II, and evidence suggests she acted as a spy. Born Gabrielle Chanel in 1883, she rose to fame with her revolutionary designs, but her wartime activities cast a dark shadow over her legacy.

During the German occupation of France, Chanel, then in her 50s, closed her couture house in 1939, claiming it wasn’t a time for fashion. She took up residence at the Ritz in Paris, a hub for German officers, and began a relationship with Hans Günther von Dincklage, a German intelligence officer 13 years her junior. Known as “Spatz” (Sparrow), Dincklage was part of the Abwehr, Germany’s military intelligence, and their affair gave Chanel access to elite Nazi circles.

In 2011, Hal Vaughan’s book Sleeping with the Enemy: Coco Chanel’s Secret War provided extensive evidence of her espionage. Drawing on French, British, and American intelligence archives, Vaughan revealed Chanel was recruited as an Abwehr agent, codenamed “Westminster” (after her former lover, the Duke of Westminster). Her mission in 1943, dubbed “Operation Modellhut” (Model Hat), involved traveling to Madrid to leverage her connections with British elites—like Winston Churchill, whom she knew personally—to negotiate a peace deal that would end the war on Germany’s terms. The mission failed, partly because Chanel’s contact, British diplomat Brian Wallace, distrusted her motives.

Chanel’s actions weren’t just opportunistic. Vaughan documented her deep antisemitism, noting she called Jews “the enemy” and blamed them for France’s defeat. She also used Nazi “Aryanization” laws to try to seize her perfume business, Chanel No. 5, from her Jewish partners, the Wertheimer brothers, though they outsmarted her by temporarily transferring ownership to a non-Jewish friend.

After the war, Chanel was arrested by French authorities in 1944 but released quickly—rumor has it Churchill intervened. She fled to Switzerland, where she lived with Dincklage until returning to Paris in 1954 to relaunch her fashion house. The Wertheimers, who still controlled her perfume empire, funded her comeback, and Chanel’s brand thrived again, her Nazi ties largely buried until recently.

The story of Coco Chanel’s controversial past during World War II, including her ties to the Nazis and her eventual comeback, finds a curious parallel in the history of two German sportswear giants: Adidas and Puma. Like Chanel, these brands emerged from a tumultuous period marked by war, personal rivalries, and complex relationships with the Nazi regime, only to redefine themselves in the postwar era and achieve global dominance. Their origins, rooted in a small Bavarian town and a bitter sibling feud, reveal how personal and political entanglements shaped their trajectories.

Adidas and Puma were founded by brothers Adolf (“Adi”) and Rudolf Dassler in Herzogenaurach, Germany. In the 1920s, the brothers worked together in their family’s shoe business, with Adi, the quieter, more creative sibling, designing innovative athletic footwear, and Rudolf, the outgoing salesman, handling business operations. Their early success came from supplying shoes to German athletes, including Jesse Owens, who wore Dassler shoes during his triumphant 1936 Berlin Olympics performance. However, the brothers’ relationship with the Nazi regime during this period remains a point of contention. Both joined the Nazi Party in 1933, though the extent of their involvement is debated. Adi was reportedly more focused on his craft, while Rudolf’s business dealings aligned more closely with Nazi officials. The brothers’ factory was repurposed to produce military boots during the war, a common practice for German businesses under Nazi control.

Tensions between Adi and Rudolf, already strained by personality differences, worsened during the war. A particularly bitter incident occurred in 1943 when, during an Allied air raid, Adi and his wife sought shelter in a bunker where Rudolf and his family were already hiding. Adi’s alleged remark—“Here come those Schweinhunde [swine] again,” referring to the Allied bombers—was misinterpreted by Rudolf as an insult directed at him. This misunderstanding, combined with disputes over business decisions and personal betrayals, deepened their rift. By 1948, the brothers split, with Adi founding Adidas (named after his nickname and surname) and Rudolf establishing Puma (initially called Ruda).

The postwar period was challenging for both companies. Germany’s economy was in ruins, and the brothers faced scrutiny for their Nazi affiliations. Adi, who remained in Herzogenaurach, was briefly investigated by Allied authorities but was cleared, possibly due to his limited political involvement and focus on shoemaking. Rudolf, however, faced harsher treatment. He was interned by American forces, who suspected him of closer ties to the Nazis, including rumors of SS connections. Rudolf believed Adi had denounced him to the Allies to gain control of their joint business, a claim that remains unproven but fueled their lifelong animosity. Herzogenaurach became a divided town, with residents and businesses aligning with either Adidas or Puma, a feud so intense that locals nicknamed it “the town of bent necks” because people checked others’ shoes to determine their loyalty.

Like Chanel’s comeback in 1954, both Adidas and Puma reinvented themselves in the postwar years. Adi’s innovative designs, such as the Adidas Samba and the three-stripe logo, gained traction with athletes worldwide.

Adidas and Puma have since acknowledged their founders’ pasts, with Adidas publicly addressing its history in a 2016 statement, emphasizing its commitment to transparency and modern values.

Today, Adidas and Puma are global powerhouses, their origins in a small town and a sibling feud overshadowed by their commercial success. Much like Chanel’s ability to rebuild her brand despite her controversial wartime actions, the Dassler brothers’ legacies endure through their companies’ resilience and innovation.