25 Ways Style & Grooming Have Changed Since 1999

25 Ways Our Idea of What Handsome Men Look Like Has Changed Since 1999

August 23, 2024

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Humans are inherently social creatures, and visual culture is a huge part of the human experience, too — so it’s no surprise that people have cared about looking good for a long time.

What’s actually seen as handsome, beautiful or stylish changes from era to era, from place to place, and from subculture to subculture.

There’s never been any one way of impressing other people with your looks — which, to a degree, makes the prospect of nailing down the biggest changes in the style and grooming world since this site was founded in 1999. Of course lots of things have changed. That’s part of the appeal.

But outside of the looks shifting, warping and getting weirder, there are still evolutions that are interesting from a philosophical point of view. So to celebrate AskMen’s 25th birthday, we’re taking a look at 25 things about style and grooming that have changed since then.

- with files from Joey Skladany & Cole Cooper

1. Clothes Shopping Goes Online

Guys in 1999 had no choice — if they wanted new clothes, they’d have to buy them IRL. Fast-forward 25 years and the realities of in-person shopping — malls, changing rooms, getting fashion advice from an employee — have all but gone extinct.

These days, the overwhelming majority of clothing shopping happens online, with many contemporary fashion brands kicking off as direct-to-consumer, without even having brick-and-mortar storefronts in the first place. The one thing we’re all waiting for is a Clueless-style clothes selection software to help plan our outfits.

2. Manscaping Becomes Standard

It’s a reality of life — testosterone means body hair. Guys have often dealt with this fact by simply letting it grow, and there’s not anything especially wrong with that — but it’s also not surprising that lots of guys prefer to live life a little more smoothly.

WE COVERED IT: A Guide to Manscaping Your Body Hair

Enter the concept of manscaping, which rose to prominence in the 2010s as it became more socially expected for men to put effort into their grooming — and as shaving technologies became more sophisticated.

3. Standout Product: Le Labo Santal 33

The fragrance market is, inarguably, oversaturated, especially with heritage brands that have churned out the same signature colognes for literal decades. When most men find their trademark smell, they stick to it for many years, if not a lifetime. That’s why it was impressive to see New York-based Le Labo emerge in 2006 with a line of scents that have evolved into cultural mainstays.

Sandalwood-heavy Santal 33, for instance, which was introduced in 2011, can be detected in the streets of practically any major city, while The Noir 29 has emerged as a customer favorite with notes of bergamot, fig, and bay leaves. Even better, most products are unisex and can be shared among partners.

Check out Le Labo Santal 33

4. Tattoos Went From Taboo to Trendy

Though there’s a history of tattooing basically all over the world for eons, in the contemporary West, they were often associated with seedy characters. Though the second half of the 20th century saw them become more common, they still remained a symbol of the counterculture and something that could easily prevent you from getting a ‘straight’ job in 1999.

WE COVERED IT: Peak Tattoo: What the Future Holds for Body Art

Today, however, they’re everywhere, including the boardroom; whether they show it off during Zoom calls or not, your CEO may well be someone with a whole arm sleeve.

5. Guys Start Getting Cosmetic Procedures Too

Plastic surgery is something with a contentious reputation — many people see it as a sign of a sick society or tragically low self-esteem. But you can’t deny that it’s becoming more popular, as those who go under the knife seem to love the effects.

WE COVERED IT: Plastic Surgery for Men

Today, you can encounter treatments like Injectables for more masculine features such as chin or jaw enhancement, botox for men (aka Bro-tox), hair transplant surgery to address male-pattern baldness, as well as the infamous tummy-tuck and facelift procedures.

6. Standout Product: Carhartt Work In Progress Faux Leather Jacket

Carhartt, a brand that’s been sold at tractor supply stores forever, has revolutionized workwear by making it chic. Carhartt Work In Progress (WIP) was created in 1994 exactly for this reason, but the past decade has seen workwear-as-fashion take over. Today, it can be seen on celebrities and influencers everywhere.

This faux-suede jacket takes the classic chore coat, known for being a go-to for manual labor, and elevates it for the technology-focused age we live in today. Complete with utilitarian pockets, this jacket is a beautiful homage to its origin.
Check out the Carhartt Work In Progress Faux Leather Jacket

7. The Rise of Fast Fashion

Clothing is a fascinating, nearly magical aspect of human culture. We’ve been dressing up in radically different ways to impress each other (and ourselves) for millennia. In today’s fast-paced capitalist landscape, there’s a lot of money to be made from satisfying people’s urges to have new and exciting outfits — but the faster the fashions switch up, the more people buy, and the more people buy, the faster the fashions change.

That’s resulted in the current fast-fashion climate, where ultra-cheap, low-quality pieces of clothing are ending up in landfills at an alarming rate. It’s not good for the planet, it’s not good for the industry, and frankly, it’s not good for our souls. When is the slow fashion trend going to take over?

8. Standout Product: Kiehl’s Facial Fuel Face Wash

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A first purchase of Kiehl’s felt like an entrance into adulthood. It was, after all, an upgrade to the store-bought beauty products we were limited to as kids and preteens. As a result, nothing felt more special and more mature than the herbal and menthol-forward scent of Kiehl’s Facial Fuel.

The brand, of course, offers so much more than a standout face wash, but it seemed like every dude carried (and continues to carry) the icy blue bottle that has practically become synonymous with men’s skincare. It also just feels good on the face, especially in the a.m., with a unique cooling sensation that jump starts a day like an ice bath or cup of strong coffee.

Check out Kiehl’s Facial Fuel Face Wash

9. Metrosexuality Expands to Encompass Everything

In the late ’90s and early 2000s, the term ‘metrosexual’ was coined to describe straight men who cared enough about their looks that they might as well be gay. The idea that any guy who wasn’t somehow ‘other’ might think to dress nicely or use products to positively impact his appearance was so strange that it required a term to describe.

WE COVERED IT: Are You A Metrosexual?

But the term lost relevance over the intervening 25 years as taking care of your body and looks stopped being such a strange concept, and became, well, the new normal.

10. Standout Product: Merrell Hydro Moc

It's official — Crocs are everywhere, and other brands are doing their own spins on the concept. We love the Merrell Hydro Moc, which is designed to be ultra-comfortable, breathable, durable and just plain strange. But strangeness makes this pair unique and fun, and isn’t that what fashion is all about? Made of EVA foam with designated openings along the top, these mocs are water-friendly and breathable.

A heel strap ensures a snug fit for active outings or walking around town. Whether you’re wearing these for a quick trip outside or dressing them up for all-day wear, you’ll step out in comfort and stand out in style.
Check out the Merrell Hydro Moc

11. The Fanny Pack Becomes the Cross-Body Bag

Was there any cringier item of apparel in the ’90s than the dreadful fanny pack? If so, we must have missed it.

Anyone who was alive at the time may have found themselves confused in the past half-decade as the fanny pack reappeared in full force — this time, with a whole new spin (literally) as it was worn diagonally across the torso, rather than horizontally across the waist. Maybe a slightly new angle was all the much-maligned fanny pack really needed to become the sex symbol du jour for young men.

12. There’s a New Focus on Skincare

Rollers to combat under-eye bags. Korean skincare masks. Moisturizing creams and oils. Face-specific sunscreens. As female beauty trends expanded from makeup to include skincare in the 2010s, men’s skincare began to crop up too in a way that simply didn’t exist in the late ’90s.

WE COVERED IT: Men’s Skin Care Products That Actually Work

These days, there are enough skincare products to absolutely blow the mind of any guy from 1999, no matter how avant-garde or dialed in he was to grooming trends. The average guy in 2024 probably isn’t too invested in them, but the idea of a man having a skincare routine is no longer outlandish, either.

13. Standout Product: Salt & Stone Natural Deodorant

There was a recent shift when men, like women, decided to pay more attention to the ingredients that went into their beauty products. And it seems like this revolution was spearheaded by the natural deodorant industry with Salt & Stone as its fearless leader.

Now that the no-frills, neutral tone-labeled brand has developed a cult-like following, they’ve expanded to include body washes, body sprays, hand creams, and even candles. The Santal and Vetiver scent is typically our top pick, but you can’t go wrong with the three that round out this environmentally friendly family: Bergamot and Hinoki, Black Rose and Oud, and Neroli and basil.
Check out Salt & Stone Natural Deodorant

14. Wet Wipes Are for Everything Now

Think like a baby — got a problem? It might be something you can solve with a wet wipe. Whether it’s stinky armpits, a butthole you’ve just pooped out of, stinky feet, or a nose you’ve just blown, some form of wet wipe may be just what the doctor (or the grooming industry) ordered.

WE COVERED IT: Best Face Wipes, Revealed

And look — it’s true that a wet wipe is a nicer thing to rub on your skin than uhh. Essentially anything that’s dry. But the phrase “Dude Wipes” is not a good one in any timeline.

15. Standout Product: Thom Browne Flannel Pleated Skirt

Men can look great in skirts too, and no one does one like Thom Browne. Taking inspiration from East Coast preppy icons, the brand created a skirt that leans more masculine. The tab closure and adjustable back strap look like traditional men’s pants with adjusters. The gray wool/cashmere blend feels warm and luxurious while the pleats add sophistication and visual interest.

With beautiful details like the dropped back hem, four-bar stripe, and the subtle but colorful Thom Browne stripe, this skirt is refined and anything besides ordinary. Easily make a t-shirt feel elegant or dress to impress by adding the matching blazer and/or jacket.
Check out the Thom Browne Flannel Pleated Skirt

16. Subscription Boxes Offer Fashion in the Mail

Though the heyday of subscription boxes has clearly passed, in the mid to late 2010s, they were a hallmark of men’s fashion, as brands like Frank & Oak and Bespoke Post offered to send you new wardrobe pieces every month.

WE COVERED IT: Best Subscription Boxes, Reviewed

The excitement of that promise may have proved to be too much, as, let’s face it, lots of guys may not need or want 12-plus new items of clothing a year, every year, indefinitely. Still, it was a bold new concept that briefly took men’s fashion by storm.