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7 ESSENTIAL STYLE TIPS FOR MEN OVER 50 BEFORE YOU SHOP

Navigating the world of fashion in your 50s (and beyond!) may seem daunting, but trust me, it’s entirely achievable. While I can’t personally guide every man receiving an AARP membership in the mail, I can offer you this comprehensive guide to dressing for mature men.

If you’re new to my writing, you might be asking yourself: Caroline, as a 29-year-old woman who spends her free time watching Nordic crime dramas and perfecting my homemade macaroni and cheese, what do I know about the style dilemmas faced by men approaching early retirement?

Well, for one, I have a soft spot for well-dressed older gentlemen.

Every man over 50 has unique wardrobe needs that reflect his personal style and lifestyle. Whether you’re searching for casual attire, looking for shopping recommendations, or simply wanting to elevate your fashion game, dressing well at this age can be just as exciting and diverse as it is for younger men.

Not sure where to begin? No need to fret! Below, 7 tips on nailing mature style for men:

Get a tailor

Everyone I’ve spoken with in the realm of men’s style, especially for those over 50, agrees on one crucial point: the difference between “a guy wearing clothes” and “a well-dressed man” often comes down to good tailoring.

Building a relationship with a tailor is essential for any mature man looking to elevate his style.

Consider your tailor your clothing’s doctor. Just as you have a dentist for your teeth, an internist for your health, and a dermatologist for those pesky moles, it’s time to have a tailor on speed dial to ensure your wardrobe is in top shape.

Now, I can already hear you thinking: “The clothes I own fit me just fine!”

But let’s be real—no man, and I mean none of you, can wear off-the-rack clothing perfectly.

Sure, you don’t need to have every t-shirt tailored or sweatpants hemmed, but those button-down shirts you wear daily with jeans or chinos? Get the sleeves adjusted to the right length.

And don’t forget about those jeans and chinos! 

What about the blazer you wear for dinner with your spouse each week? Could it use a little adjustment to fit you better?

Think of this process like visiting a doctor. You don’t go in every day for every little issue, but for the significant matters, you want to consult a professional. 

Focus on the finishing touches 

When it comes to presentation, the key differentiator between well-dressed men and those who simply wear clothes is the extra attention to detail. These subtle touches may not be immediately noticeable, but once you see them, they make a significant difference.

This attention to detail extends beyond your clothing to grooming, including a well-maintained beard (and nose hairs!), clean nails and cuticles, and a pleasant scent. Just look at the smart tie and coordinating socks worn by Stanley Tucci—voted the most stylish man of 2023 by Style Girlfriend followers!

Accessories are an excellent way to elevate your style as a man over 50. A beautiful scarf can enhance a simple blue overcoat, while the right shoes can complete your outfit—just as easily as the wrong ones can ruin it.

Investing in accessories is a smart choice for your wardrobe. Timeless pieces, like a classic pair of glasses, will never go out of style, and if you choose quality items built to last, you’ll enjoy them for years to come.

I’d like to highlight timepieces: they’re one of the first things I notice on a man. If you wear a watch, I can’t help but notice which one it is.

Let me be clear: you don’t need to spend a fortune on a watch. However, if you can invest in a quality timepiece, it’s often worth it. Even an affordable tank-style Seiko can make you look polished and distinguished.

Invest in forever pieces

By avoiding fleeting trends, you can invest more wisely in your wardrobe. Why? Because when you focus on timeless pieces, you know you’ll wear them for more than just one season.

Instead of purchasing multiple inexpensive shirts and trousers, consider buying one or two high-quality staple items. Then, invest in having those pieces tailored to fit you perfectly. The final step? Embrace the ease and simplicity of cultivating a signature personal style!

Look for brands that prioritize craftsmanship and quality. 

While you may not have the budget to splurge on every item in your closet, you can be strategic about your spending.

Identify the pieces you wear most frequently. If you rarely wear sweaters but often don blazers—think of a post-presidential Barack Obama—prioritize your budget accordingly to reflect your lifestyle.

Lean into a Monochromatic Color Palette

Monochromatic dressing involves combining pieces from the same color family to create a cohesive and polished look. This style not only elongates your body but also gives you a sleek, modern appearance with minimal effort.

Take, for example, the character Steve Martin, 79, plays on Only Murders in the Building. He often sports monochromatic ensembles, like blue jeans paired with a white shirt and a blue knit sweater or overcoat.

For men over 50, these outfits are not only simple to assemble but also effortlessly elevate your style.

You can approach monochromatic dressing in a few different ways. Our favorite at Team SG is the black and blue route—opting for rich, deep blues like navy—or embracing earth tones, such as pairing tan chinos with a chunky oatmeal rollneck sweater.

Aim for leveling up your personal style instead of chasing trends

Here’s a little secret: I often share this advice with my younger clients, but it’s especially true for older gentlemen—dressing for who you are, rather than trying to keep up with the latest trends, makes all the difference.

By midlife, you’ve witnessed countless trends come and go, which makes it easier to identify which cuts and styles flatter you and which colors and textures enhance your personal aesthetic.

Consider what clothing aligns with your lifestyle and which pieces don’t quite fit who you are. 

Think of this guideline not as a limitation, but as a permission slip to bypass fleeting trends. That’s a true luxury! As men age, they naturally become more distinguished—there’s a reason the term “silver fox” is a compliment.

Allyson B. Fanger, the costume designer for Netflix’s (criminally underrated, in my opinion) *Grace and Frankie*, shared that one of the joys of dressing older characters like Robert and Sol—played by Martin Sheen and Sam Waterston, both in their eighties—is that these men have lived rich lives.

The show features two lawyers who leave their wives for each other after their kids have grown up, and their style is spot on.

Robert and Sol don’t need to evolve further in their fashion choices, which makes dressing them all the more enjoyable for Fanger.

They each have favorite brands, signature color palettes, and distinct approaches to style.

Robert is traditional, favoring button-down shirts and chinos—he’s a Brooks Brothers man through and through.

Sol, on the other hand, embodies the spirit of a hippie, opting for Cubavera camp shirts and comfortable Tommy Bahama linen pants.

These characters exemplify how, regardless of personal taste or style, it’s entirely possible to achieve top-notch personal fashion at any age.

Ultimately, knowing who you are and being confident in that is the cornerstone of any man’s style, and that understanding becomes more profound as you accumulate life experience.

Adopt a wardrobe uniform

Larry David, at 76, is a big advocate for uniform dressing. While many people think of a daily uniform as a traditional suit and tie, David exemplifies how versatile and liberating this approach can be.

He’s a king of casual style—if you’re searching for casual clothing ideas for men over 50, the *Curb Your Enthusiasm* star offers an excellent blueprint.

His go-to wardrobe staples include crewneck sweaters, zip-ups, AG 5-pocket chinos, and soft shoulder blazers. 

If the thought of choosing an outfit every day feels overwhelming, this dressing strategy might be perfect for you. 

Consider building a capsule wardrobe filled with a few pieces you love: your favorite pants, a handful of shirts that make you feel your best, and some knitwear or jackets.

And don’t hesitate to buy items you adore in multiple colors! (This is another trick David uses.)

This way, each morning, you can reach into your closet and confidently know that whatever you pick will likely coordinate beautifully.

Be yourself 

It might sound a bit silly to wrap up a list of style tips with a reminder to just accept yourself, but hear me out. You might think, “My style is just a ripped sports jersey and Crocs,” and to that, I say: maybe it’s time for a change! (Just kidding… or am I?)

What I really mean is don’t overthink dressing for a particular age. These style tips are helpful if you’re unsure where to start or want to elevate your look. But if you already have a signature style or enjoy dressing outside the norm, don’t let the number in front of your age hold you back. Embrace what makes you unique and wear it with confidence!

CONCLUSION

In conclusion, navigating style in your 50s and beyond doesn’t have to be a daunting task. Embrace the principles of good tailoring, invest in timeless pieces, and build a wardrobe that reflects who you are. Remember, personal style is all about confidence and authenticity—wear what makes you feel good, whether it’s a classic blazer or a funky shirt.

Don’t shy away from experimenting with accessories and details that can elevate your look. And most importantly, don’t let age define your fashion choices. Celebrate your individuality and express yourself through your clothing. After all, style is a lifelong journey, and it’s never too late to redefine your aesthetic!

OLD MONEY AESTHETIC FOR MEN – COMPREHENSIVE GUIDE

In an era dominated by fast fashion and fleeting trends, the old money aesthetic offers a refreshing departure. Rooted in tradition and sophistication, this style exudes a sense of timeless elegance and understated luxury. It’s a look that transcends fleeting fashion cycles, appealing to those who appreciate quality, craftsmanship, and a refined sense of style.

This comprehensive guide will delve into the key elements of the old money aesthetic for men. Whether you’re looking to elevate your wardrobe or simply appreciate the beauty of classic style, this guide will offer valuable inspiration.

WHAT IS THE OLD MONEY AESTHETIC?

The “old money” aesthetic, also known as quiet luxury, draws inspiration from the understated, sophisticated style of those who have inherited their wealth rather than earned it. It emphasizes preppy, monochromatic looks and discreetly luxurious clothing, focusing on high-quality, logo-free designer pieces, expert tailoring, and classic American prep.

This fashion trend is defined by timeless, enduring pieces that prioritize quality over fleeting trends. It’s a nod to the refined elegance associated with historic family dynasties like the Kennedys, Gettys, and Vanderbilts.

In recent years, the old money aesthetic and quiet luxury have gained popularity among Gen Z and Millennials, who are drawn to its nostalgic appeal and commitment to classic, chic pieces that stand the test of time.

Style icons such as Jackie Kennedy Onassis, Paul Newman, and Princess Diana, as well as fictional characters like Blair Waldorf and Chuck Bass, have helped popularize this trend.

OLD MONEY AESTHETIC IN HOLLYWOOD

A quintessential Hollywood character who embodies the old money aesthetic is Dickie Greenleaf, portrayed by the handsome Jude Law in the 1999 film The Talented Mr. Ripley. Dickie epitomizes quiet luxury as a charming, eccentric multi-millionaire who inherited his wealth. He leads a carefree lifestyle in Italy, favoring rebellion over the constraints of Manhattan, where he enjoys anonymity and the freedom to indulge in his desires without scrutiny. In Italy, he feels no pressure to marry or pursue a traditional career; instead, he spends his days enjoying his allowance, frequenting jazz clubs, and escaping the expectations of his wealthy parents.

Another notable character that represents the old money aesthetic is Jay Gatsby, famously played by Leonardo DiCaprio. Gatsby is an incredibly wealthy young man residing in a grand Gothic mansion in West Egg. Renowned for his extravagant lifestyle and lavish Saturday night parties, he remains an enigma—no one knows his origins, his profession, or how he acquired his fortune. Wearing a neatly tailored tuxedo can certainly evoke the impression of an old money mob boss, exuding the refined elegance that comes with inherited wealth.

HOW TO ACHIEVE THE OLD MONEY AESTHETIC FOR MEN

Recently, the phrases “stealth wealth” and “quiet luxury” have come to define the old money aesthetic, which centers on understated elegance and refined sophistication. While the clothing may seem simple or unexciting at first glance, it is typically of exceptional quality. If you aspire to embody the old money aesthetic as a man, here are some styling tips to help you achieve that distinguished look.

MEDIUM-LENGTH HAIRSTYLE IN A CLEAN-CUT MANNER

The “old money aesthetic” for men’s hairstyles often features long to medium-length cuts. Classic, clean-cut styles, such as the undercut, side part, slicked back, wet mop, and messy curtain, serve as the foundation of this look. A prime example is Dickie Greenleaf, a character from The Talented Mr. Ripley, who sports a stylish blend of a messy curtain and side-part hairstyle.

Jay Gatsby’s slick back hairstyle perfectly embodies the old money aesthetic, characterized by sophistication and timeless elegance.This hairstyle, often paired with tailored suits and classic accessories, highlights Gatsby’s pursuit of refinement and his enigmatic persona. If you’re looking to achieve a similar look, consider using a strong styling gel or pomade for a sleek finish, and opt for well-fitted clothing that complements the sophisticated vibe.

MUTED AND SOFT COLORS (MEDITERRANEAN STYLE)

Before diving into the specific styles, it’s important to establish some prerequisites for achieving the old money aesthetic. When it comes to color, focus on muted, soft tones like white, cream, and baby blue.

The men’s old money aesthetic incorporates elements of cottagecore and soft boy fashion, but with a more refined emphasis on masculinity and elegance. Steer clear of bright, bold colors that lean toward the progressive. Instead, envision a time when wealthy billionaires spent their days on yachts rather than in underground clubs or racing expensive sports cars.

ALL-WHITE TENNIS OUTFIT

To effortlessly embody the old money aesthetic, consider sporting an all-white, tennis-inspired outfit. Brands like Lacoste and Rolex can provide great inspiration. An all-white ensemble not only exudes a “summer in the Hamptons” vibe but is also incredibly versatile, fitting seamlessly into various aesthetics, including preppy styles.

LOOSE-FITTING LINEN BUTTON-DOWN SHIRTS

When the weather is warm, a loose linen shirt is one of the best options to achieve the old money aesthetic. Opt for neutral colors like white, cream, or baby blue.

A loose-fitting linen shirt, reminiscent of Dickie Greenleaf’s style, sends a clear message: you prefer spending time on a yacht rather than toiling away in a 9-to-5 office cubicle.

CASHMERE SWEATER OR CARDIGAN

As the weather turns colder, layering becomes essential. Consider incorporating cashmere sweaters or cardigans into your wardrobe. Cashmere is often seen as a symbol of luxury among woolen fabrics due to its richness and softness.

This luxurious wool comes from a specific breed of goats native to regions like India, and it has gained a devoted following for its exceptional quality. If you haven’t experienced cashmere yet, it’s definitely worth trying!

WEAR A CARDIGAN OR SWEATER OVER THE SHOULDERS

There’s an undeniable charm in wearing a cardigan or sweater draped over your shoulders that perfectly embodies the “old money aesthetic,” especially when paired with a sophisticated set of sunglasses.

This style not only adds an element of warmth but also enhances your overall look. However, thickness matters—avoid bulky, heavy knit sweaters that can overwhelm the outfit.

Opt for cashmere, as it adds a refined tone and texture to a vintage button-down shirt or polo underneath. Just ensure that the sweater is in a slightly different color from the shirt for a well-coordinated appearance.

POLO SHIRTS AND CHINOS

A polo shirt is a great way to achieve a polished look without appearing overly effortful, especially when styled with a French tuck or tucked in completely. This adds a touch of European flair to your outfit. When paired with tapered chino pants, you’ll perfectly embody the old money aesthetic. A polo is a timeless piece and a wardrobe staple that every man should own.

BLACK OR BROWN LOAFERS

When it comes to footwear, a stylish pair of loafers is the perfect finishing touch for your old money aesthetic outfit. They exude class, especially when paired with straight-fit chino pants. While you can certainly add a pop of personality with brightly colored or patterned socks, loafers are typically worn without socks—or with no-show socks for a clean look.

CLEAN MINIMALISTIC WHITE SNEAKERS

While high-end designer sneakers may be pricey, they tend to clash with the old money aesthetic, leaning more toward a starboy vibe.

Instead, opt for clean, minimalistic white sneakers. The neutral color exudes class and sophistication. Consider styles like Adidas Stan Smith or Alexander McQueen for a refined touch.

CONCLUSION

Remember, the old money aesthetic is about more than just appearances. It’s about embodying a certain ethos: respect for tradition, appreciation for craftsmanship, and a commitment to understated elegance. By embracing this aesthetic, you’re not just following a trend; you’re investing in a timeless style that will serve you well for years to come.