How to Be Timeless

Co-authored by Christina Santelli

Ever notice how some famous people seem to become beloved icons while others seem to fade into nothingness? As an example, rappers J-Kwon and Jay-Z both had major hits on the Billboard Top 100 in 2004, but only one of them is still putting out successful albums and scoring prestigious guest spots today.^{[1]
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Research source} There's no sure-fire way to predict what sorts of looks and attitudes will be popular in the future, but with a few common-sense strategies, it's not hard to give yourself the right ingredients for lasting popularity — the rest is a mixture of hard work and luck!

Method 1

Method 1 of 2:

Looking Timeless

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Choose clothing with "classic" appeal. If you're interested in looking timeless, start by considering clothing choices that have already been proven as timeless. While many trends in fashion come and go, some basic outfits stay more or less the same over time. Below are just a few outfit ideas for men and women that have been popular for at least a quarter-century and likely will be for the near future:
- Women: Skirts with blouses, jeans with tee shirts, black tights, simply-patterned dresses, flats, heels.
- Men: Shirt-and-tie combos, suit jackets/blazers, fitted dress pants, medium-to-dark jeans, polo shirts, medium-length tee shirts, sneakers, dress shoes.
2
Prioritize simple, minimalist outfits over complicated ones. Having a timeless look is often as much about what you don't wear as it is about what you do wear. A timeless look is one that doesn't "try too hard" to catch others' attention. Instead, it lets the wearer's natural good looks speak for themselves. Try to wear mostly simple, unpretentious pieces of clothing, rather than flashy, overly-showy pieces. Whites, blacks, one-color items, and simple prints are good ideas — neon colors and overcomplicated patterns are not.
- Not only will this give you a timeless look, but it will also save you money in the long run as you shop for clothes. Simple pieces of clothing (especially items that are either white or black) can be used in a huge range of outfits and still look good, while flashy pieces usually give you much more limited options and require you to buy more clothing to compensate.
- For a great example of timeless fashion from the world of TV, consider the cult classic 90s show Twin Peaks. In show that's filled with sometimes-garish late 80s/early 90s fashion choices, the show's main character, detective Dale Cooper, looks about as good today as he did back then. By wearing mostly simple, elegant suit-and-tie combinations, he avoids looking like a stereotypical member of Generation X and instead achieves timeless appeal.
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3
Wear clothing that fits you naturally. Almost every outfit will look best on you if your clothing fits well. While it may occasionally be fashionable to wear clothes that don't fit properly in a conventional sense, these sorts of fashion choices are unlikely to beat the long-term appeal of clothing that fits you well. If you're shopping for formal clothes, don't be afraid to spend a little extra money at a tailor's to get your outfits looking just right. For casual clothes, you can be a little more forgiving about getting your fit exactly right, but it's still in your best interest to pick clothes that fit your figure comfortably without being too loose.
- As a very general rule, clothing that's especially tight or especially loose is often part of a temporary trend or fad. For example, think of the tight pants worn by men in the disco scene in the 1970s — they were popular at one point, but today, it would be almost unthinkable for a man to seriously wear skin-hugging white polyester slacks. Keep this in mind if, for example, you're considering shopping for skinny jeans to give yourself a modern hipster look!
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Don't go overboard with accessories. One or two great accessories can be the "cherries on top" of a timeless outfit — on the other hand, wearing a dozen flashy accessories can be a great way to date yourself. Below are just a few great accessory ideas for men and women — try to pick one or two at maximum and tend towards simple, elegant accessories rather than large, attention-seeking ones.
- Women: Jewelry/earrings, purse/backpack, sunglasses, light makeup/lipstick, bracelets, painted nails, scarves
- Men: Dignified watches, ties, simple cufflinks, backpack/messenger bag/briefcase, sunglasses, jewelry or medallion (preferably worn around the neck and under the clothes)
- For a textbook example of how to use accessories, look up photos of Audrey Hepburn in her prime. The most famous photo of the actress shows her in-character for the movie Breakfast at Tiffany's with plenty of jewelry and a long, skinny cigarette holder that would look fairly out-of-fashion today. However, the photos of Hepburn out-of-character are another story — she usually wears simple, one-colored tops accompanied with elegant earrings and light makeup for a look that's as striking today as it was decades ago.
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Keep a natural, clean-cut hairstyle. Some hairstyles belong to a certain time and place, while others virtually never go out of style. For example, it's difficult to think of a "beehive" hairdo without thinking of out-of-date style that housewives wore in the 1960s. On the other hand, a woman who wears an ordinary bob or simply lets her hair grow out won't necessarily scream, "2010s!" in a few years. Below are just a few ideas for hairstyles that aren't likely to go out of style any time soon:
- Women: Bobs, "fringe" cuts, long natural hair, layered cuts, ordinary ponytails, braids, bangs (optionally)
- Men: Crew cuts, buzz cuts, short parted hairdos, shaved heads. Light application of gel or pomade is OK.
- As a very general rule, hairstyles that require lots of maintenance or upkeep are less likely to be timeless than others. For example, a spiky liberty mohawk, which requires daily application of hair products to keep it standing up, will almost always call to mind the punk scene of the 70s and 80s. There are, however, some exceptions — dreadlocks, for instance, can require some work to maintain, but can be a perfectly timeless look for someone with naturally kinky hair.
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Be conservative with tattoos and piercings. When it comes to being timeless, modifying your body permanently is something you'll want to be very careful about. You can always throw out or donate tasteless clothes, but piercings and (especially) tattoos can be much harder (and more expensive) to get rid of. Never get a tattoo or piercing on a whim — instead, talk to your friends, your family, and your tattoo artist/piercer to discuss whether it would be a smart long-term choice. When in doubt, err on the side of safety and don't get the tattoo or piercing. It's never embarrassing not to have any tattoos or piercings.
- Keep in mind that, unfortunately, potential employers may make judgements about you based on your tattoos or piercings. It's not fair, but it's true — many employers report that tattoos (especially those on the hands or face) can make an otherwise-qualified applicant seem unsavory.^{[2]
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- Women have a little more freedom with piercings than men do. For example, it's not at all unusual for a woman to have earrings, but it's still sometimes considered unconventional for men to wear them, especially in formal settings. Many women can even pull off wearing a simple nose stud in a formal context, while this would be very unusual for a man to do.
- As a general rule, if you're getting a tattoo, it's wisest to get it somewhere on your body that isn't ordinarily exposed (like your chest, ribs, back, and so on.) This way, even if your tattoo ends up being a source of embarrassment in a few years, you won't have to show it to anyone you meet.
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Beware of styles that became popular only recently. If there's one major rule to take away from this section, it's this: avoid fashion trends that are popular today but weren't popular in the past, because these are almost certain to become unpopular again sooner or later. Fashion trends are constantly changing — a piece of clothing or a haircut that's "in" today may be majorly embarrassing in just a few years' time. However, by sticking to the classic, timeless suggestions above (which have changed only a little over the last few decades) you'll stay looking great for years to come.

Method 2

Method 2 of 2:

Acting Timeless

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Don't be afraid of aging. Having a timeless sense of style is as simple as buying some new clothes and getting a good haircut. Becoming a timeless person, however, is another thing entirely — you'll need to attempt the difficult tasks of unfocusing your attention from the here and now and getting a broader perspective on life. To start, try to place less of an importance on the passage of time in the first place. Don't worry about growing old — trying to stay young forever or recapture past glory days will only date you. There are few things more awkward than someone who's aged out of a certain social group trying desperately to stay "cool" in the eyes of the younger members.
- If you're worried about growing up or aging, it can help to look at the benefits of these things, rather than just the scary and sad parts.^{[3]
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  Research source} For instance, while adults may sometimes fall out of touch with old friends, they also have lots of opportunities to make new ones while devoting their energy to a fulfilling career. Older people also usually have the advantage of maturity and experience over younger people, which can make things that used to seem like a big deal (for instance, peer pressure) seem like no big deal at all.
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Be true to yourself, not passing trends. A timeless person has a self-identity that doesn't change depending on what's currently popular. Don't make any conscious choices to redefine yourself based on what other people think. Instead, any change in the way you see yourself should come about naturally and effortlessly over time. Don't look down on yourself if you don't conform exactly to what's popular today. Popularity is fleeting and can change at a moment's notice — the sense of peace you get from being true to yourself, on the other hand, lasts forever.
- Beware: living your life to be trendy at all costs without considering your true feelings can cause significant problems in the long run: for instance, you may waste time and money trying to get a hold of the latest clothes and consumer goods, you may lose sight of who you truly "are" as a person and suffer identity confusion, and more. Being true to yourself avoids all this.
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Don't compare yourself to other people. In the words of Teddy Roosevelt, "Comparison is the thief of joy."^{[4]
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Research source} It's a common piece of life advice to avoid comparing yourself to other people because it's ultimately pointless and will almost always lower your self-image. This habit isn't just a surefire way to become insecure and unhappy, however — it will also keep you from being timeless. Spending your time worrying about how everyone has a better life than you robs you of the time and energy you need to grow as person. Rather than changing and maturing naturally, you become static, forcing yourself only to make changes as a reaction to other people and never because of your true feelings and desires.
- For young people, avoiding harmful comparisons to other people can be as simple as resisting peer pressure: for example, you shouldn't abandon your tried and true friends once you get a chance at hanging out with the "cool kids." Why be stressed about appearing unpopular when you can simply enjoy your time spent with your true friends?
- For adults, this can be more complex: for example, you won't want to compare yourself unfavorably to a coworker who has all the latest tech gadgets or a new car. These things are sources of fleeting pleasure, not lasting satisfaction, so they have no bearing on your status as an individual. If you're true to yourself and this person is not, you're the happier person, no matter what car you drive.
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Have an appreciation for great things from the past. Someone who's living a timeless life won't be obsessed only with media and art that's currently popular. Instead, she'll have a rich variety of interests that shows an appreciation for the great works of the past and a discriminating taste for the best that the modern world has to offer. A timeless person understands, for instance, that while the language of great books, movies, and music may eventually start to seem old-fashioned, the thoughtfulness and emotional resonance of these works don't diminish with time. Below are just a few select examples of pieces of media that are widely considered to be timeless (there are many, many more.)
- Books:^{[5]
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  Research source}Ulysses, To Kill a Mockingbird, Lolita, Catch-22, Native Son, I, Claudius, Pride and Prejudice, A Brave New World.
- Movies:^{[6]
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  Research source}The Godfather, Citizen Kane, Vertigo, The Shawshank Redemption, Casablanca, Apocalypse Now, Alien.
- Music: Revolver (The Beatles), Dark Side of the Moon (Pink Floyd), Aquemini (Outkast), What's Going On (Marvin Gaye), Blood on the Tracks (Bob Dylan), Thriller (Michael Jackson), London Calling (The Clash).
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Pick timeless role models. A timeless person knows that's wise to pick inspiring people to look up to and to learn from their example when possible. The people who inspire us can be famous people who've achieved great things, people who have shown incredible strength and integrity, or simply friends and family members who have given our lives meaning in some way. Don't waste time worshiping at the altar of pop celebrities — instead, pick a genuine role model with something more substantial and long-lasting to offer you. Below are just a few examples of role models who are truly timeless
- Jesse Owens: A black American who won four gold medals at the 1936 Olympics in Berlin, Germany, single-handedly humiliating Adolph Hitler and disproving the Nazi doctrine of Aryan racial superiority.
- Florence Nightingale: A british nurse who selflessly treated wounded soldiers during the Crimean war whose contributions to the field of nursing helped improved the terrible conditions of hospitals at the time.
- Sri Chinmoy: Indian spiritual leader who founded the Oneness-Home Peace Run, an event in support of world peace.^{[7]
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- Note also that role models don't necessarily have to be real people — fictional characters can also be sources of inspiration in your life. A well-written character like, for example, Atticus Finch from To Kill a Mockingbird can be a great role model. In this example, Finch's tremendous strength of character and sense of justice can be an inspiration to anyone who wants to create these qualities in herself.

Expert Q&A

Question

What makes something classic?

Christina Santelli
Professional Stylist
Christina Santelli is the Owner and Founder of Style Me New, a wardrobe styling concierge based in Tampa, Florida. She has been working as a stylist for over six years, and her work has been featured in HSN, the Pacific Heights Wine and Food Festival, and the Nob Hill Gazette.

Christina Santelli

Professional Stylist

Expert Answer

Something is classic when you reach for it all the time. For example, Diane Von Furstenburg was the first designer to make a wrap dress 50 years ago, but those dresses are just as relevant today. They're iconic because they look good on everyone, regardless of their body type.