Pair of Kings: A Fashion and Culture Podcast · Pair of Kings

How to Dress Better in 2026: An Actual Men's Style Guide by Pair of Kings | 13.19

·1 hr 29 min·5 clips

A tailor can make cheaper clothes look better than expensive clothes off the rack.

1. Pair of Kings: A Fashion and Culture Podcast closes Season 13 with a menswear episode about dressing better in 2026. 2. Saul Thompson hosts with cohost Michael Smith, and both are named on the show as Instagram-linked style commentators who wear the clothes they discuss. 3. The episode asks what a real style guide should do instead of acting like an affiliate-link shopping list. 4. Saul says many style guides are “glorified shopping lists” and complains that GQ disclosures appear before useful advice. 5. He reads a GQ preppy-style headline about “resurgent Ivy look” and contrasts it with the actual history of Ivy style at Yale. 6. Saul mentions post-Jim Crow university integration and says fashion writing should explain how a look was formed, not only what to buy. 7. The hosts criticize the habit of citing ASAP Nast as a style reference without much explanation of his music or influence. 8. Michael shifts into memories of Rick Owens outfits, Fear of God joggers, St. Laurent pieces, and the older online fashion forums where these labels circulated. 9. Saul objects to “investment piece” language and says clothing should not be treated like a commodity or resale strategy. 10. He argues that people should buy clothes they will actually wear to work, bars, dinners, and ordinary outings. 11. Saul’s first concrete rule is to find a tailor and learn terms like “full break” and “half break.” 12. He says a cheaper suit that is tailored can fit better than a much pricier off-the-rack suit. 13. Michael backs the point with a long-running rule: wear new clothes often so denim, boots, and jackets break in properly. 14. He says many garments look bad at first and improve after years of wear, repair, and repetition. 15. The hosts connect style to daily life by saying clothes should match a job, hobbies, and routines instead of waiting for a vague special occasion. 16. They also argue that people should learn how to wash and care for garments, especially by avoiding dryers for many items. 17. The tone stays conversational and argumentative, with jokes about Joe Pesci, Belgian accents, old boots, and fashion-nerd memory tests. 18. The format mixes critique, personal wardrobe examples, and a running back-and-forth between practical advice and jokes. 19. People who like menswear, tailoring, and fashion-critique podcasts will get the most from it. 20. People looking for a quick shopping list or celebrity outfit roundup may skip it.

As heard by us

A blunt, funny reset on style-guide talk that keeps its advice practical.

Pair of Kings spends this finale on a familiar target: style advice that sells itself harder than it teaches. Saul Thompson and Michael Smith keep the talk loose, and the strongest moments are the plain ones, where they talk about buying with intent, tailoring, and looking after…

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Why you'd press play

Skip the affiliate sludge and get a blunt reset on dressing better.

Read the full recommendation in PlayNext →

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