In 1995, high on my love for Keanu Reeves and the scent of Herbal Essences shampoo, I walked into my hometown Gap and spent $20 on a casually distressed denim jacket—arguably one of the wisest wardrobe purchases of my life.
All blue wash and brass buttons, that jacket draped my shoulders through many adolescent triumphs and growing pains. And I still have it today; it's not just a nostalgic relic that reminds me of Jessie Spano or my Green Day phase—it’s actually on active rotation in my wardrobe. And for good reason.
A killer jean jacket is the ultimate in-betweener. It’s a workhorse that can easily add just the right amount of youthfulness or dimension to your look. It’s versatile and classic but can also add a jolt of "now" just by styling it as an unexpected under-layer (try it buttoned-up under your blazer).
So here—to help kick off those cooler temperatures of fall in style—is a shopping guide to five unique jean jacket styles in various shades of indigo (and black!)—all destined to be an epic, memorable purchase.
The Inky Blue Classic
Remember in the season finale of Mad Men, Don Draper had this newly minted man-of-leisure vibe? You can echo it with a medium-wash, trucker-style denim jacket, like this one by Kenzo. Just switch out Don's traditional crisp spread collars for a white crew neck T-shirt, and wear a darker-wash denim on your bottom half, and you’re ready for wherever the Pacific Coast Highway (or the weekend) will take you. ($576, matchesfashion.com)
The Black Waxed
Nothing toughens up a look quite like black. But for an extra dose of ruggedness, add the weathered texture of waxed cotton. The fabric is known for aging uniquely to you, and looks great in the shape of this atypically masculine jacket by Alexander Wang. Bonus points to Wang for the additional hardened details like the leather collar and slanted zip pockets. Wear it with more black, of course. ($1,125, mrporter.com)
When deciding between the two most timeless, no-fuss transitional jacket options—a bomber or denim jacket—why not go with both? A denim bomber like this one by Mr. Start is lightweight yet sturdy, warm but breathable—making for a reliable wardrobe mainstay for unpredictable weather. Wear it with a fine-knit sweater and sneakers. ($475, eastdane.com)
Remember: The perfect denim jacket should mold to your body and be worn-out in all the right places—which is made easier if you pick a light heritage wash like this casually distressed option by Joe Fresh. And if you want to wear it as a layer—under a tailored overcoat or other kind of jacket—choose a trim yet slightly boxy fit and go a size down. The torso should hit right at your waist and the sleeves should reach just below your wrists. Then you can wear it in lieu of a cardigan—buttoned-up and layered underneath your favorite overcoat when the temperatures finally drop below 50 degrees later. ($59, joefresh.com)
The pop of off-white faux shearling at the collar of this retro-inspired jacket by Maison Margiela is the modern equivalent of the standout contrast-collar on the Lee Storm Rider denim jacket—which was made a cinematic and style icon when screen giant Paul Newman wore it in his 1963 film Hud. Team yours with a pair of rugged, brown boots—another Newman-endorsed item. ($1,630, mrporter.com)