6 Menswear Books Every Guy Should Own
Military, workwear, Ivy—these are the books that defined my approach to timeless style.
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THE BEST WAY TO learn about menswear is through physical books. Of course it’s helpful to skim Reddit threads, read articles online, and watch YouTube videos for free. But nothing gives you deeper, more reliable knowledge than a well-researched book.
I’ve learned this as a writer covering menswear for a full decade now.
Another benefit of owning physical books: you can build a library to revisit for referencing and creative inspiration. Just last week, I found myself flipping through my copy of Icons of Men’s Style by Josh Sims—which led me to this story I’m writing today.
The 6 Best Books on Men’s Style
The books I’m about to share might differ from other menswear lists you’ve read. That’s because they carry an Americana lens—rugged, timeless, sporty, and free-spirited. These are books for the Live a Little guy looking to elevate his personal style.
The great thing about Americana style is there’s usually an original reference point to look back to. Many times, those references come from the military, workwear, or Ivy League. Once you understand that history, you can tie almost anything new back to its source, which helps you make smarter investments and curate a wardrobe that’s timeless and easy.
These books are also fun to read. There’s tons of images, historical notes, and pop-culture references that’ll make you go, “Oh, so that’s where that comes from.”
Read more: 46 Vintage Style & Gear Finds for the Adventurous Man
Give this roundup a read and let me know your favorites. At the end, I’ve got a shortlist of seven additional menswear books that belong in every guy’s library.
Icons of Men’s Style
by Josh Sims
Josh Sims’ Icons of Men’s Style is an all-time favorite menswear book of mine. I originally bought it thinking it would break down famous men with great style (hence Paul Newman on the cover), but I was surprised to discover it’s a book that breaks down essential items.
Inside you can get history on items like the peacoat, denim jeans, desert boots, and beyond. I love how the book uses imagery to make the history more digestible. If you buy Icons, I recommend the small “mini” size version with Newman on the cover. It’s harder to find, but it looks cool on a bookshelf and is easy to carry to the park or coffee shop.
The Details: Iconic Men’s Accessories
by Josh Sims (again)
The Details is Sims’ follow-up to the Icons book. The Details zooms in on the smaller items a man should own: watches, sunglasses, cowboy boots. There’s even sections on socks and underwear—two garments I believe should be made uniform and refreshed yearly.
If you want to go deeper on personal style, then it only makes sense to pair The Details with Icons. How you complete an outfit makes all the difference, and The Details helps you master the art of the finishing touch.
The Rebel’s Wardrobe: The Untold Story of Menswear’s Renegade Past
by gestalten, Bryan Szabo, Thomas Stege Bojer
This coffee table book with James Dean on the cover digs into the outlaws, misfits, and counterculture figures who shaped how we dress today. Beyond Dean and the cowboy types, The Rebel’s Wardrobe also covers athletes, bikers, punks, and skaters—basically anyone who intentionally breaks rules.
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It’s the kind of coffee table book you’ll actually use. Rich imagery and with explainers on how everything from denim to fatigue jackets went mainstream. Great for sparking conversation.
Take Ivy
by Shosuke Ishizu, Toshiyuki Kurosu, Hajime Hasegawa, Teruyoshi Hayashida
I mentioned Take Ivy in my winter reading list, but it absolutely deserves a spot here too. Published in 1965, it documents a group of Japanese men who came to the U.S. to photograph American style on Ivy League campuses.
It’s filled with images of college students hanging in dining halls, walking around campus, and studying in the library. If you want to understand the DNA of modern menswear, this is a must-read.
A Man & His Watch
by Matt Hranek
Matt Hranek’s 2017 book interviews men about their favorite watches. It might seem niche, but watches are a vital part to menswear. Watches often carry meaningful stories tied to family or major life moments.
If you understand the importance and lore behind watches, and watch collecting, you can use that knowledge in conversations with new people you meet. One of the easiest ways I’ve found to spark up a conversation with a stranger is by commenting on their watch.
The Outdoor Archive
by Chase Anderson, Clint Pumphrey, Chris Burkard (Foreword)
These days, the clothes we wear often have technical fabrics or functional features that trace back to original outdoor apparel. That’s why the last book I’m recommending revolves around the outdoor industry.
The Outdoor Archive provides a wide landscape of outdoor clothing through vintage advertisements and marketing materials—from heritage brands like L.L. Bean to mountain climbing gear from The North Face. (There are no Patagonia ads, but that’s ok. There’s plenty of source material to dig into outside of them.) Similar to The Rebel’s Wardrobe, this book looks great on a coffee table and makes a fun group read.
