StyleFall 2026
8 Style Moves from the 90s That Have Us Excited for Fall
The trends of our formative years have circled back. Turns out we still like a lot of them.
Thanks to Thursday Boot Co. for supporting Primer's mission and partnering on this piece.
Sometime in the mid-2000s, I read in Esquire that straight fit jeans were out and skinny jeans were in. I did not take it well.
Lesson one about trends: they change whether you'd like them to or not. Live long enough and you get lesson two: they circle back, every 20 or 25 years or so. (See: pants, loose, after a decade of slim and skinny.)
When that happens, a certain guy says “been there, done that,” like he's evolved past it and the rest of us haven't caught up. Fair enough. But lately, instead of dreading the comebacks I don't like, I've been trying to remember the ones I do instead.
Middle and high school were when most of us first started paying attention to clothes, and a surprising amount of it fits into my current personal style. Fall is when getting dressed gets fun again.
MOVE â„– 01
Funky sweaters
The 90s did not do subtle. Teal and purple was the color scheme for sports teams, that paper cup, and every bus seat in the country. Bring some of it back:
- Brighter colors
- Bigger patterns
- A looser knit
All three de-business-casual a sweater. If you wouldn't wear it to a job interview, you're on the right track.
The Original Westerley Cardigan Pendleton
Also pictured: Vintage Soft Boxy Tee, Gap
We featured it this spring as an alternative to the Project Hail Mary sweater, and it's finally cold enough to wear it. I bought mine a size up for the full drapey, cozy effect. Worn large, it's hard to ignore, which is funny for a beige sweater mostly worn by grandpas and The Dude.
Also pictured: Court in Earth Suede, Thursday Boot Co.
Think of it as the opposite of a quarter-zip. Playful, and clearly on purpose.
TopcoatMOVE â„– 02Peacoat
The short wool jacket
Station Jacket in Elmwood Thursday Boot Co.
Also pictured: Denim shirt (similar: Flint and Tinder, budget: Levi's), M-51 Cargo Pant, Relwen
A good wool coat used to mean a topcoat (too formal, too warm for some men) or a peacoat (great, if the naval thing is your thing). Thursday Boot's Station Jacket is the third answer, and it gets there by sharing its cut with your denim trucker, waist length and all. Which means you already know how to wear it. Over a dress shirt, it's dressy. Over a band tee, it goes just as easily.
Thursday built it like real outerwear: 18 oz. wool with a quilted, insulated interior. Also in olive, navy, and black, mine is the Elmwood, a brown glen plaid houndstooth straight out of 90s prep.
True to size with room for layers (mine's a medium).
Origin note
Glen plaid, briefly
Glen plaid is a Scottish wool check built from two ideas: blocks of houndstooth, that small four-pointed check, and fine stripes running between them. Together they stack into bigger boxes.
Weave it brown on brown and from across the bar, it looks like rich, textured wool. Within arm's reach, surprise: plaid. A reward for standing close.
MOVE â„– 03
Fuller pants, worn higher
Rise
The khakis and chinos of the 90s sat at your natural waist and had real room in the leg. Many of us were sagging our jeans, sure, but anything dressier got worn fuller and higher, which is higher than the last fifteen years trained us to wear anything. I've learned to love the comfort and proportions they add to an outfit's silhouette again.
Leg
On the label, look for relaxed fit or classic fit. Then mind the break, which is how much fabric bunches up where the leg meets your shoe.
Break
A fuller pant that looks sloppy is usually just a fuller pant that's too long.
Keep it to a half break, or a conservative full break, and all that fabric hangs straight and clean from waist to shoe. Don't feel like visiting a tailor? Flip up a cuff.
MOVE â„– 04
Chunky boots
Confession: the first thing that got me excited about looser pants, before I'd even come around on the pants, was the boots. Your boot silhouette is almost entirely decided by your pant silhouette. Skinny jeans wanted something like a slim, low-profile Chelsea, and for a decade they got one. Put that same Chelsea under a fuller leg and a perfectly good boot goes missing.
More pant wants more boot: a bigger shape, a thicker, chunkier sole.
The Diplomat
I've had mine in cinnamon suede for a couple of years and I love them, partly because they feel like boots I had in the 90s. The raised stitch across the toe is the moc toe, and it does two jobs: it gives the boot some visual heft, and it lands the whole thing closer to the J.Crew catalog than the Army Navy store. Fully lined in glove leather, so they're comfortable out of the box, with a cork-bed midsole that forms to your foot. Also featured here in the other outfits in the dark Tobacco leather.
The Explorer
A tall, nine-eyelet boot Thursday calls “a streamlined take on the traditional American combat boot.” I've owned three other pairs of Thursdays in this exact dark olive suede. It's my favorite thing they make. Olive shoes sound flashy right up until you wear them, at which point it goes with everything a brown boot goes with. People will like your boots without being able to tell you why. It's also what helps all that height and heft from looking like you're a paratrooper. WeatherSafe suede on Vibram soles, keeps you vertical and dry well into winter.
MOVE â„– 05
Cargo pants
When I was in my 20s, I bought a '78 Corvette. When it was factory new, that car was cool. Ten years later it was just somebody's old used car. By the time I bought it, when it was 30 years old, it had aged all the way through to vintage. Hate to break it to you, fellas, but we're 30 years out from the Gap and Banana Republic cargo pant trend we loved. Style kryptonite since about 2009, they're on the Corvette's schedule now.
- NEWCool!
- 10
yearsSomebody's used car - 25+
yearsVintage
Cargos are here.
Also pictured: Station Jacket in Elmwood, Denim shirt (similar: Flint and Tinder, budget: Levi's), Diplomat in Tobacco · More cargos: Old Navy
MOVE â„– 06
T-shirt over long sleeves
The official “I like music” look of the 90s and 2000s.
Family Guy even did a whole bit about it. It came up through skate and grunge, on Nirvana and Pearl Jam and everyone at their shows. Before that, the story goes, 80s metalheads and punks pulled band tees over long sleeves so the shirt still showed when it got cold. No designer required: guys were chilly and wanted you to know what they listened to.
Calling it a classic is a stretch for a guy in two t-shirts. Heritage fits better: around a long time, popular for only some of it. Worn now, it comes off as neither defiant nor outdated. And if your fall runs warm, it's layering you won't overheat in.
MOVE â„– 07
V-neck over a crew tee
Peak 1990s, by way of the 1890s.
- Late 1800s
- The v-neck started as late-1800s sportswear, cut low to show off the neckwear.
- 1913
- The crew t-shirt started as Navy underwear in 1913, until Brando and Dean promoted it. Eventually the tee slid into the V where a collared shirt used to sit.
- 1990s
- The 90s made it a uniform, the decade's answer to casual-dressy purgatory: dressier sweater, no collared shirt, looser khakis. You saw it on Friends. You saw it on everyone, really.
Chunkier, looser knit looks more coastal rather than accountant to me. With fuller chinos it sits right alongside the minimalist palette of the 2010s.
MOVE â„– 08
Interesting belts
For most of our lives, a man's belt was a thick strap of leather with a square buckle. It was allowed to have one job, and contributing to the outfit wasn't it. Three that do more:
Big in the 80s and 90s, back by way of Buck Mason, Todd Snyder, and Ralph Lauren.
The belt of the 1990s. Everybody had one. Every father had one. No holes, so it fits wherever you need it to. Wear it a little too long, like a rake.
Under three quarters of an inch, it arrived with the higher-waisted trouser. Buck Mason puts it in a lot of their photos. If you've been following along, this should surprise you. Fuller pants asked for a bigger boot, so a higher rise ought to ask for a bigger belt. It went the other way. The thin belt is there so the waist doesn't get any busier than it already is.
High-waisted pants were everywhere in the 70s too, held up by buckles the size of hood ornaments. The pants returned and the buckles stayed home. Trends come back changed, with different proportions and different company. Which is why none of this looks like a 70s costume, or a 1995 one.
ONE MORE THING
If you came up in the 90s, you don't have to learn any of this. You already have the instinct. You just stopped using it when everyone else did. Go refind the moves you liked, rediscover what you loved about them, and update or incorporate them into the other moves you love now.
