A Men’s Guide to Tasteful, 90s-Inspired Outfits

three men wearing different 90s style outfits

It seems every few years or so, the general public decides that some decade or other is officially “back.”

Perhaps out of desire for nostalgia, our culture seems to periodically revive various eras of music, film, art, pop culture – and fashion. Only, in more recent years, it feels as if we as a society have elected to entertain multiple decades at once.

After all, why only dedicate our collective hype to the 80s, when the 70s were arguably just as fun, just in a different “font?”

Side by side images of a man wearing a 60s, 70s, and 80s outfit

Vintage and retro styles may not be as unfamiliar to you as you might imagine. Even a lesser-trained eye can often distinguish between various decades of dress, because each one had its own signature elements and unique flavors.

Among the most nostalgic decades, for many, is the 1990s, the close of the twentieth century. “90s kids” alone have become something of an early internet meme that persists to this day, and much of the media from that era, sitcoms, movies, music, video games, and more, hold a special place in the hearts of many who lived through it all.

Perhaps a bit more divisive to some, is the fashion of the 90s. The thing is, 90s menswear, like it or not, definitely served its own incredibly unique vibe. In recent years, this vibe has been revived from time to time, whether that’s the return of chunky white New Balance sneakers, slouchier suits, or bright, expressive colors.

man wearing a vintage 90s style track suit in blue and yellow accent colors

With the revival of some of these trends, it’s proven that despite their arguably “dated” look, some styles never truly go out of style – at least not forever. It may always carry with it that sort of 90s connotation, but that’s not necessarily a bad thing.

A lot of people love 90s styles, and we’re quite partial to many of its elements, as well. So, if you’re looking to try out a bit of tasteful, retro-inspired aesthetics, here are a few ways to get started without screwing up.

90s Sneakers

One of the easiest ways to dip your toes into the world of 90s style is by treating them to some old-school kicks. In the late 2010s, the chunky “dad” sneaker trend saw the reemergence of brands like New Balance, Asics, and even Skechers as cool, exciting style sources with a touch of modern hype.

chunky white New Balance style sneakers

Almost everyone who grew up in that era can remember the types of sneakers their dad wore: big, chunky sneakers in either highly neutral or oddly colorful palettes, oftentimes leather, mesh, or some hybrid of both – usually from New Balance or a similar brand.

On the other end of spectrum, slimmer sneakers like the ever-popular Adidas Samba were equally huge in the 90s, often taking up space in skater subcultures and the like.

Adidas Sambas

Footwear is arguably the simplest way to try out a bit of retro style. In the case of evergreen shoes like the Adidas Samba and the like, it’s hardly even a statement, given how popular they are today, but either choice of chunky or slim sneaker can lend a bit of 90s flare to your wardrobe without committing too much of yourself to any given aesthetic.

90s Athletic Wear

Another easy, laid-back method to getting comfortable with simple and accessible 90s style is through their athletic wear trends, which, thankfully, are easier to replicate now than ever due to their resurgence in popularity as of late.

We’re talking no slim Lululemon jogging leggings or dri-fit running jackets, and instead going for a looser, natural-fiber-based ensemble. A good pair of cotton sweatpants is a good place to start (with elastic in the waist, but that doesn’t count in our book).

Make sure the leg opening is wide rather than tapered or of the elastic “jogger” variety, allowing your sweats to spill over your sick-ass 90s sneakers in a satisfying and laid-back way.

man wearing loose gray sweatpants with a wide leg opening and a matching gray crew neck sweatshirt with a red number 90 on the chest

Then, a matching crew-neck athletic sweatshirt is a fine addition, too. You’re going to want a slightly boxier fit and a medium crop on the hem. Brands like Russel, Nike, Champion, New Balance, and more, are all your friends here.

For a great, slightly exaggerated take on a more 90s-adjacent pair of sweatpants, check out new brands like Poolhouse New York, or if you’re on a slightly tighter budget, check out some of Uniqlo’s more recent options.

90s Denim

If you’re ready to start taking 90s style a bit more seriously, particularly within the denim department, you’re in luck, seeing as how the majority of contemporary clothing brands today have been offering jeans in 90s-inspired cuts and fits for a few years now.

While there is no one definitive style of jeans that the 90s claims full ownership of, in general things were a lot looser than the slim-skinny trends of the 2010s. It’s hardly a secret that slim-fit bottoms have been on the out these last few years, but now more so than ever, looser jeans are having a true moment.

Don’t worry though – loose doesn’t have to mean baggy if that’s not your speed. We’re just talking about a relaxed fit through the seat, thigh, and leg, but if it fits you properly on the waist, you’re golden.

man wearing relaxed fit light wash jeans with white chunky running shoes and white tee shirt

A really great pair of 90s-esque jeans will often be a medium to light-wash, though any wash will do, with a medium rise and a wider leg opening to allow for a visually interesting “pant-shoe interaction.”

In a lot of fashion spaces, that phrase is the subject of some eye-rolling, but its a very real thing that does indeed affect the overall vibe of an outfit.

A leg opening that’s too small or tapered won’t rest as well over your shoes, leading to a look that just doesn’t give off the cool, laid-back energy of the best 90s-style jeans. So, keep it in mind!

For an easy, accessible gateway into decent denim that fits the way a 90s pair of jeans should, consider offerings from brands like Madewell, Levi’s, Abercrombie & Fitch, and more.

90s Knitwear

Once you’ve got your jeans all settled, we’d recommend you consider the world of 90s style knitwear! Sweaters during this decade did see some slip-ups, like a growing reliance on synthetic fibers, but there were still plenty of pure wool and cotton options to be found.

man wearing a chunky cable-knit sweater and an image of a man wearing a brown wool sweater vest cardigan over a white tee shirt

A good 90s sweater was at its best when it was chunky and offered a generous fit, especially in the width of the sleeves. The humble sweater vest also received a bit of fanfare, making its way into business casual wardrobes of young professionals.

Don’t believe us? Just ask Chandler Bing from Friends. Or some of the costume designers over on Seinfeld.

90s Suiting

In many ways, some of the most distinguishably 90s looks are derived from the suiting and tailoring trends of that decade. In the 1980s, suits became reinforced as symbols of aspiration and wealth, with Wall Street and various business sectors propping up the iconic “power suit,” usually something dark, double-breasted, with big, padded shoulders and a drapey cut.

man wearing an 80s style suit, navy blue, pinstriped and double breasted

In the decade to follow, a lot of these trends carried over, but they did relax a little bit for the majority of the population.

While this decade was probably when the suit first began to see a real decline in popularity, tailoring was still standing on some fairly strong legs.

Looser, drapey cuts were still big, but some of the shoulder padding and overall jacket structure was lost on many of the favoured styles of the era. Both styles really existed simultaneously, in truth.

man wearing a 90s style, relaxed, unstructured speckled gray wool sport coat over a white tee shirt and blue jeans

Shades of navy, gray, and tan were quite popular in the business world, with longer, proper length jackets and wide-fit pleated pants that still sat comfortably high on the waist. Striped dress shirts were a popular pairing with the suits of the day, as were tasteful uses of color to add some contrast.

For some of the best illustrations of iconic 90s tailoring styles, one need only examine a vintage Armani ad from the era. Like we said, a lot of the 80s trends were carried over, but instead of coming with a sharp, powerful edge, the tailoring of the 90s was often a bit less structured and sometimes styled a bit more casually.

For the best of both worlds, try finding a more structured-yet-drapey fitting double breasted suit with wide lapels and pleated pants in shades of either navy or gray – pinstriped/chalkstripes are fair game, too!

On the other side of the spectrum, try styling a relaxed, unstructured sport coat made from materials like silk or wool blends, with low gorges on the lapel for good measure.

80s/90s style gray double breasted suit with a low buttoning point

One of the unifying details you’ll find on a lot of 90s suiting, existing in both camps, are lower buttoning points on the jacket, often situated quite close to the waist. This creates an elongated lapel and provides a lot of room to show off an interesting tie or patterned shirt.

90s Suiting Accessories

Lastly, on the subject of accessorizing, we’ll pick up where we just left off – accessories as they relate to the world of suiting.

The neckties of the day took a very abstract shift from the more geometric patterns of the 80s, but like a lot of the trends, there’s some overlap to be found. Some of the colors and patterns utilized during this era might appear a bit, well, ugly to some people today, But in our opinion, that’s what makes them interesting! They were a bit risky, and often, it worked!

two ties side by side, one is purple and features an 80s-eque geometric pattern, the other is also purple but has a more abstract design

Additionally, there’s the matter of suspenders, or “bracers” as the Brits call them. These saw a massive revival in the 1980s, and for those still trying to channel the vibes of the classic “power suit” in the 90s, they did see some continued popularity.

What made the suspenders of this time period rather unique were their bold patterns and colors, often made from fine silk.

Playing off the rich designs of an appropriately 90s necktie, and there’s a recipe for some real magic here.

The 90s, Wrapped

There’s so much more to the world of 90s style, but looking at it as a whole, it can be difficult to tell where to begin confidently if you’re trying to experiment more with retro aesthetics.

That’s why some of the identified looks featured in this article were written as they were – to inform, educate, and advise you on which 90s looks can be pulled off with minimal effort, and which ones work today with ease.

Thanks to the popularity and lasting influence of 90s style, you won’t look out of place with this gentle experimentation, and once you’ve got the basics down pat, you can continue to explore more and more of the exciting, and wildly unique styles of the 1990s.

FAQs – 90s Style Guide

Where can I find quality 90s-inspired clothing today?

Look for vintage shops, thrift stores, and online platforms (like Depop or Etsy), plus modern brands that feature retro collections.

What 90s hairstyles or grooming trends work well with these outfits?

Consider low-maintenance cuts like textured layers or a subtle mullet, and incorporate accessories like scrunchies or minimalist headbands for that retro touch.

How do I adapt 90s fashion for a professional or business environment?

Opt for tailored 90s-inspired suits or blazers with the era’s relaxed structure, and pair them with modern accessories to keep it polished and workplace-appropriate.

What common mistakes should I avoid when recreating a 90s look?

Steer clear of over-accessorizing, extreme bagginess, or clashing color schemes. Aim for one statement piece paired with updated basics.

Are there any 90s trends best avoided in a modern wardrobe?

While nostalgia is fun, excessively baggy jeans or overly bright athletic gear might feel dated unless styled thoughtfully.

Can I integrate 90s style into everyday wear without looking like I’m trying too hard?

Yes—you can start by incorporating a single retro element (like a classic pair of 90s sneakers or denim) into a largely modern outfit for an effortless nod to the era.

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