Men’s 90s Fashion Trends Worth the Comeback

Let’s reverse the clock to a simpler time when choosing a favorite Power Ranger was the dilemma of the day. A time when seeing the Beast chasing Benny in “The Sandlot” was a daily occurrence on VHS. Or, when kids would race home from school to catch the most-requested music videos on “TRL.” If you haven’t guessed yet, we’re taking it all the way back to the nostalgic 90s. Men’s 90s fashion is resurfacing and inspiring a new generation of style enthusiasts. From snapbacks and skater shoes to double-denim looks, we dive into what’s worth bringing back. Ready to incorporate (dare we say) vintage vibes into your current-day outfits? Stay tuned, home skillet, to find out how.

While trends tend to blend from one decade to the next, there was a distinct pendulum swing in the 90s. Moving away from elaborate neon getups of the 80s, the end of the millennium embraced a more laid-back approach. We can sum up the overarching theme of this movement in three words: casual, cool and comfortable. From the streets to mainstream culture, self-expression was a major influence on 90s casual fashion for men. From unkempt grunge styles and oversized, logo-laden outfits to preppy flair, there was something for everyone. Are you chomping at the bit to emulate these throwback men’s 90s outfits? Take a chill pill and keep reading because we’ve got you covered. 

90s-Inspired Grunge Fashion for Men

Music has the power to inspire beyond the stage, and this rings especially true in the 90s. Iconic grunge bands defined not only an angsty sound but also a subculture of style. Plucked from the lyrics of Nirvana song, “Smells Like Teen Spirit,” grunge embraces a “come as you are” attitude. Look to Kurt Cobain, who pulled off  90s grunge fashion for men the best. To copy his unbothered, ever-disheveled appearance, invest in loose jeans with distressing detail. We’re not talking about subtle whiskering or fading but full-on holes, rips and fraying. Pair your denim with a band tee and toss on a well-loved flannel shirt. Matching jeans with shoes is easy for men’s 90s fashion. Skater boy meets punk rocker when you finish off the look with worn-in Vans or Converse sneakers. Lastly, grow out your mane for supreme head-banging abilities. 

Dress Like Your Favorite 90s Sitcom Character

Ever have the itch to dress like sarcastic Chandler from “Friends” or kindhearted Eric Matthews from “Boy Meets World?” If so, please welcome the normcore trend to our men’s 90s fashion conversation. Normcore is, at its core, overwhelmingly plain. Before you dismiss it as sounding boring, just wait. Lovingly referred to as a “show about nothing,” Jerry Seinfeld made average guy attire effortlessly cool on “Seinfeld.” Take a page from the comedian’s playbook with a denim on denim 90s outfit for men. Tuck a chambray button-up into well-fitting 501s with a braided belt. Feel free to match blue on blue denim or mix it up with black-wash jeans. To keep the look authentic, wear a sleek pair of sports sneakers as a nod to the character’s shoe obsession. 

In fact, Complex credits Jerry Seinfeld as a major influence to sneaker culture both on- and off-screen. Other sneakerheads like Will Smith, Martin Lawrence and many others helped athletic kicks transcend from function to fashion. The craze is alive and well today. Dr. Dre, Snoop Dogg, 50 Cent and Eminem all wore fresh kicks during the Super Bowl LVI halftime show. It’s further proof that the 90s are here to stay. If you’re interested in sneaker history or enjoy collecting rare Nikes or Jordans, you’ll fit right in. 

90s-Inspired Street Style for Men 

Inspired by city life, men’s street style is always on-trend because it doesn’t fit into a specific category. It rejects traditional designers and instead caters to real-life scenarios. What are guys actually wearing while they walk their dog or meet up with friends? If you’re interested in 90s street style for men, we’ve got a couple of ideas for you. In case you haven’t noticed, blue jeans and cargo pants were closet staples for gents in this era. Paired with a plain white T-shirt, you have a versatile, blank canvas to work from. Now, you can choose to go in two different directions with your men’s outerwear to top off your 90s outfits

Although there are many interpretations of street style, we couldn’t fail to mention the archetypal windbreakers of this time period. Trickling in from the 80s, windbreakers featuring color blocking in bright colors was a common choice for outerwear. Vibrant hues are topping the charts for men’s fashion in 2022, so opt for a mix of oranges and reds. Keep the brights coming with a pair of high-tops in a coordinating shade of tangerine. This color combo will work for you to ensure you’re looking all that and a bag of chips. 

If daring shades aren’t your thing, no worries. Paparazzi often spotted Brad Pitt in 90s menswear sporting a real leather jacket over his jeans and tee. This simple layer proves how easy it is to level up your look without much effort. Lean into the “bad boy” persona with lace-up combat boots and part your hair down the middle. Other heartthrobs like Leonardo DiCaprio and Nick Carter owned this hairdo and current young celebs are following suit. Timothée Chalamet and K-pop boy band members of BTS, just to name a few. Backstreet’s back, alright?

90s-Inspired Hip-Hop Fashion for Men

In the land of TV, some might argue that in West Philadelphia, 90s hip-hop fashion was born and raised. On “The Fresh Prince of Bel-Air,” Will Smith was not only the king of his throne but also of style. Fellas, now’s your chance to dig those snapbacks from the shadows of your closet because it’s their time to shine. In Will’s world on the show, funky prints and primary colors were the names of the game. Attending a 90s-themed party? Honor his original aesthetic with a sideways hat, cotton basketball shorts, geometric-patterned shirt, high socks and retro Wayfarers. For a modern twist on men’s 90s fashion, couple a classic striped T-shirt in subtle hues with overalls. Keep one shoulder strapped for an oversized shirt or wear it with both straps buttoned up. Smell ya later.

All jokes aside, 90s hip-hop fashion wouldn’t be the same without the famous rappers of its time. Tupac, Jay-Z, Notorious B.I.G. and others brought the oversized men’s 90s outfits to life. Baggy jeans and jumbo team jerseys were a coveted combo in the hip-hop industry. If you’re open to exploring looser denim silhouettes, take this as your sign. While slim-fit jeans will always be a classic choice, why not give a relaxed fit a go? To keep things current, opt for a well-fitting shirt to complement your build. Finally, channel LL Cool J and reach for a bucket hat with a prominent logo across the front. Now you’re looking fresh and fly. 

Jet Set In 90s Celebrity Airport Outfits

After a couple of years of staying home, you might be ready to hop on a plane to an exciting destination. If traveling is in your future, tuck the joggers away and dress to the nines. Back in the day, people used to utilize the airport as their fashion runway. Nicolas Cage’s airport uniform in the 90s was an iconic look. In true 90s men’s fashion, recreate his outfit with a killer pair of jeans. The true star of the show was a bomber jacket with a sheepskin collar. Hello, Tom Cruise in “Top Gun.” Reminder: these are 90s-inspired styles, so don’t feel limited to leather. Explore other materials like corduroy or velvet for a different take on texture play. Denim jackets make our travel essentials list as an easy and lightweight layering option. Grab your duffel bag and you’ll be ready to bounce. 

The 411 on 90s Preppy Styles for Men

From the characters on “Clueless” to Princeton-bound Carlton Banks, it’s no surprise preppy attire made its mark on the 90s. Fast forward 30 years, and it’s still going strong. In fact, we’re seeing a revival of Ivy League-inspired outfits as a major focus in men’s spring 2022 fashion. Are you into court sports or love a polished appearance for brunch with buddies? Lean into the preppy 90s clothes of yesteryear for an old-school twist. Think sweater vests, varsity jackets and popped collars. A performance polo partnered with khaki hybrid shorts will serve you well on and off the green. Swap the shorts for trousers and drape a cardigan over your shoulders for supper at the country club. No matter which elements of preppy style catch your eye, you’ll stay looking sharp among high-society elites. 

Men’s 90s-Inspired Summer Fashion

In the 1990s, men’s summer fashion centered around chill vibes and having a good time. Planning to shoot some hoops on the first official day of summer? Do as the 90s kids did and go sleeveless in a tank top paired with drawstring shorts. High-top sneakers reign supreme, along with a flat brim cap to keep the sun out of your eyes. Now, who could forget a prominent accessory of this era? The hip pack, aka fanny pack. A solid place to keep six feet of Hubba Bubba Bubble Tape secure. Guys used to wear packs around their waist, but nowadays, sling them across your chest instead. You’ll also channel the all-terrain vibe of the current gorpcore fashion trend while taking it to the streets. Queue the 90s summer anthems because the sun is out and we’re ready to dust off our Macarena moves. 

Booyah—now you’re up to speed on all things 90s-inspired fashion for men. Are you ready to give these throwback threads a chance? Get started today and share your style goals with a styling expert. A box of five curated items will arrive on your doorstep so you can try before you buy. While you wait, head over to Stitch Fix Freestyle™ to instantly purchase pieces curated for your style and size. Keep what you love and return the rest. Shipping, exchanges and returns are always free.

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