My first jean jacket came from a garage sale in the suburbs of Iowa. Out on a scooter excursion with the child I was nannying that summer, I placed a kid’s toy and the Levi’s classic on a card table. Five dollars felt expensive, when that was about my hourly rate. “You’ll have this forever,” the woman said, folding the jacket into a plastic bag that bounced as it hung from my scooter’s handlebars as we rode home for naptime.
That woman at the garage was correct. Denim jackets are about as close to timeless as any one article of clothing can be. Variations arise with the ebb and flow of trends, but a simple, heavy version in a mid-wash looks as natural on James Dean as it does on Michelle Obama.
Of course, the Americana-inspired jean jacket is always going to be one of those classic staples that will hold timeless appeal. Just like a khaki trench, it’s an essential style item that seems to find a secure spot in our wardrobes year after year—even if it spends a little time in-between hanging in the back of your closet.
For those who may have been keeping their blue jean babies tucked away, here are a handful of no-fail tips from denim experts that are sure to help inspire a whole new era of denim jacket-wearing for you. Read on for their advice on how to style a jean jacket now.
Tess Sullivan in lived-in denim-on-demim
Tess Sullivan
The lived-in look
Despite the many tempting versions and inventive iterations of reworked denim pieces—like cropped jackets, full skirts, and even shoes—we can’t underestimate the power of a jean jacket in its most original form. There’s something to be said for the iconic button front with two front chest pockets and cuffs, and its wonderfully worn-in feel.
Tess Sullivan, head of design and creative at Buck Mason, agrees that a great denim jacket depends on the details, specifically, “rigid 12-13 oz cotton twill, built with authentic details, and a great lived-in wash: The more life it looks like the jacket has seen the better.” Sullivan has built the sartorial world of Buck Mason’s womenswear to feel like the kind of store frequented by your friend who’s always “stumbling” upon vintage lamps at the Rose Bowl or road tripping through Wyoming; it’s cool, but not aloof. A great jean jacket feels the same.
Luckily, jean jackets are pretty easy to come by secondhand, as my own garage sale anecdote attests. And the bonus is that secondhand jackets already come with that “lived in” look.
Denim on denim
Whether you’re digging through thrift bins or buying new, Sullivan has some tips to get that denim jacket je ne sais quoi. Her first styling formula, denim on denim, is your classic Canadian tuxedo effect. “I tend to style denim together with similar washes which makes it feel more like a suit,” she explains, referring to a laid-back jeans-and-jacket pairing.
Photographed by Phil Oh
Lean into light
To achieve a head-to-toe denim outfit without looking like you’re ready for the rodeo, take a street-ready approach to denim-on-denim by coordinating oversized and distressed jean separates in stiffer, structured light-wash denim. Mixing in some of your best accessories doesn’t hurt either.
Denim, dressed up
For a more elevated look, Sullivan offers a second formula, coordinating your jacket with more formal pants, or a skirt. “The jacket takes the seriousness out of a dressy bottom,” she says, adding that the combination works especially well for special occasions. “Show up to an event in a denim jacket and a black tuxedo pant and you’re automatically the coolest person in the room.”
Jesica Wagstaff in her denim jacket.
New proportions
Fit, when it comes to denim of the jacket variety, is everything. Jesica Wagstaff, a writer and expert dresser, welcomes denim jackets in every wash, so long as they’re slightly oversized. “The fitted denim jacket of the early aughts is too limiting in terms of form and function,” she says. “A slightly larger jacket can be worn on its own, over a sweater, or under outerwear as an added layer, ensuring you’ll reach for it again and again.”
In the dark
On one episode of my favorite fashion podcast, Covered by Natalie Brennan and Ruby Redstone, the hosts take a deep dive into Levi Strauss’s three original denim jacket archetypes from the 1900s. Naturally, I suspected they’d have some opinions on how to style a jean jacket for this century—and I wanted to hear them.
“My best tip is to take note of what is catching your eye, whether that’s online, in shops, or on your friend. And if it’s the latter, I really recommend that you ask to try theirs on,” suggests Brennan. That’s how I found my beloved jacket! With denim, finding the right fit is everything.” Her personal preference? Contrast stitching and a dark wash, and ideally, in a set with matching jeans. And, if you are lukewarm on the classic jean jacket silhouette, there is no harm in choosing a denim chore coat, button up, or shacket in denim as a compromise.
Photographed by Phil Oh
Wear it your way
Wearing all of your favorite wardrobe essentials at once is also a no-fail solution for easy, elevated style. A classic blue denim jacket is no exception, looking minimalist and eternally chic when mixed with an oxford shirt, leather belt, and well-tailored trousers. Or, keep it simple with the most basic, but foolproof white tee.
Whatever you decide, it is true that a jean jacket really can accompany any look. But as timeless as it is, denim really is one of the most personal fashion preferences. Everybody’s different. The denim we keep carries memories of nights out, botched job interviews, and lavish summer picnics—and denim jackets are no different.
That’s why, even after years of neglect, I’ll never get rid of the perfect, medium wash Levi’s denim jacket hanging in my coat closet. It’s seen too much.
