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!

15 WAYS TO STYLE THE LITTLE BLACK DRESS

The little black dress (LBD) is a timeless classic that never goes out of style. Once reserved for specific occasions, it’s now a versatile option for almost any event, including weddings and formal gatherings. Every wardrobe should include at least one LBD because it’s adaptable for all seasons and styles. In summer, keep it simple and cool, and for winter, layer it up with chic outerwear.

This effortlessly stylish piece can be dressed down with a denim jacket and slides for a casual day look, or elevated with sparkly accessories for a more formal vibe. If you’re a wedding guest looking to create an elegant outfit, try refreshing your LBD with a few thoughtful styling choices from the ideas below to make it uniquely yours.

HOW TO WEAR LITTLE BLACK DRESS?

Here are some essential do’s and don’ts for styling your little black dress:

DO’S

  • Layer Up: Add denim or leather jackets for an edgy touch.
  • Incorporate Patterns: Use stoles or scarves to introduce some color and pattern.
  • Elevate with Footwear: Choose statement heels, stylish sandals, or chic boots to enhance your look.
  • Accessorize Wisely: If your outfit feels plain, opt for statement jewelry or stylish bags, but be careful not to overdo it.
  • Belt It: Wearing a belt can define your waist and create a flattering silhouette.
  • Dress for the Occasion: Always consider the event and choose your accessories accordingly.
  • Add a Blazer for Work: For an office-appropriate look, pair your LBD with a formal blazer.

Don’ts

  • Skip Shiny Leggings: Avoid wearing shiny, metallic leggings underneath your black dress; they can clash with the overall style.

By keeping these tips in mind, you can effortlessly style your little black dress for any occasion!

TIPS TO STYLE LITTLE BLACK DRESS

DENIM LOOK

Our favorite combination features a little black dress (LBD) paired with a worn-out denim jacket. This perfect blend of comfort and style inspires us to create a chic outfit. For a girly and youthful vibe, consider statement jackets adorned with embroidery, sequins, or studs. This daytime look is ideal for Spring and Summer, perfect for those laid-back days. The nude block heels add a touch of sophistication while keeping the outfit balanced. We adore the addition of a chain bag and stylish shades, making for a casual and fun ensemble.

HOW CELEBRITIES WEAR BLACK DRESS

BFFs Kendall Jenner and Gigi Hadid are the epitome of both friendship and fashion goals. They consistently wow us with their style, whether strutting down the runway or strolling through the streets of New York. Here, they both shine in stunning black dresses that are truly red carpet-worthy. Kendall’s long silk gown features exquisite lace detailing, exuding elegance. In contrast, Gigi’s mesh dress showcases geometric patterns, giving her a cool and edgy vibe. Both stars opted for minimalism with sleek black shoes, foregoing any bold colors. However, for those looking to add a splash of color or flair, statement heels or eye-catching bags would be perfect accessories to elevate these looks.

LITTLE BLACK DRESS WITH BOOTS

Kim Kardashian’s Yeezy boot trend shows no signs of fading anytime soon. We’re obsessed with how this black dress is styled with over-the-knee boots, creating a striking Fall look. The trendy waist slit adds a unique twist, setting this dress apart from the rest. This casual street style is sophisticated enough to make a great outfit for a coffee date. To complete the look, consider accessorizing with a long handbag or a stylish tote for added flair.

STATEMENT NECKLACE

A wide neckline like this one makes it effortless to style with chunky statement necklaces. This vintage piece of jewelry can beautifully elevate a basic black dress. It’s not just for formal events; you can also wear it on days when you want to feel a bit more dressed up. Whether you’re going for a casual outing or a night out, this necklace adds a touch of elegance to any look.

FORMAL STYLE

How adorable is this minimalistic yet formal evening look? To recreate it, pair your little black dress with stylish stockings and cute lace-up pumps. The tiny handbag and watch serve as the only accessories, maintaining a chic and understated vibe. For a touch of shine and sparkle, consider adding small pearl danglers to complete the ensemble. This look is perfect for any elegant occasion!

WINTER LOOK

Upgrade your winter wardrobe with a chic little black dress that’s perfect for the colder months. Pair with a cozy overcoat or tailored jacket for added warmth and style. Pair with stylish knee-high or ankle boots to keep your legs warm while looking effortlessly stylish. Finish the look with a stylish scarf and a statement handbag for a polished yet cozy winter outfit.

SPARKLY OUTFIT

This sparkly little black dress is just what you need to ring in the New Year in style. The chic fur pumps perfectly complement the fancy outfit and are on-trend for the season. For a bold statement, add a pop of color with a vibrant red handbag, or keep it sleek and sophisticated with a nude clutch. Either way, you’ll be ready to celebrate in glamorous fashion!

LEATHER DRESS

If you’re a big fan of all things leather, here’s some outfit inspiration for you. Pair your favorite black leather skirt with tights for a cool, edgy look. We love the sunglasses and chain bag as understated accessories.

PRINTED COAT 

The simplest way to give your little black dress a fresh makeover is by embracing a monochrome look. Adding a printed jacket can introduce both pattern and color to your ensemble. We love this black and white jacket, which perfectly enhances the monochromatic vibe. The addition of stylish shades and heels injects a touch of sass into the overall appearance. While this outfit is designed with maternity in mind, it’s versatile enough for anyone seeking a chic everyday look.

SIMPLE JEWELRY & FLATS

Probably an obvious one! Let me explain. I could wear it to a graduation party. I like wearing black with brown boots or shoes and my necklace is actually navy, but it looks good too. Black dresses (or mostly plain dresses) are a great canvas for a variety of jewelry options.

Classic Look

A black dress is the ultimate choice for achieving a classic look. Opt for a timeless silhouette, such as an A-line or sheath style, that flatters your figure and exudes elegance. Pair it with sophisticated accessories like a string of pearls, a sleek clutch, and classic pumps to enhance the refined aesthetic. Finish the outfit with a tailored blazer or a trench coat for added polish, making it perfect for any occasion, from a formal event to a dinner date.

STRAPLESS LITTLE BLACK DRESS

A strapless dress is a versatile choice for events like proms, weddings, or parties. If you prefer to cover up a bit, draping a fur stole or cape over your shoulders adds a classic vintage touch to the look. Pair the dress with sleek black or metallic stiletto heels for an elegant finish, and don’t forget to adorn yourself with gems and jewels to elevate the ensemble. Silver or gold danglers can bring a touch of sparkle, ensuring your black outfit shines beautifully without overwhelming the overall aesthetic.

LITTLE BLACK DRESS FOR WEDDING

There are so many elements of this cute little black dress that we absolutely adore. The ruffled waist detail adds a charming touch, while the crisscross skirt creates a slimming effect on your legs. Minimalist heels and a black handbag complement the dress perfectly, enhancing its overall appeal. As we’ve seen, black is increasingly embraced as a wedding dress color, providing a stunning contrast to traditional white weddings and exuding grace and elegance.

LACE DETAILS FOR SUMMER

You can never go wrong with a timeless classic like this black lace dress featuring intricate cutwork detailing. This versatile piece can be styled in numerous ways; for instance, wearing it over a black t-shirt adds sleeves for a sophisticated and polished look. The nude heels help neutralize the outfit, while the handbag offers a smart touch that keeps the overall appearance formal yet elegant. The turtleneck eliminates the need for a necklace, making it a statement piece on its own.

WITH CAMEL COAT

Here’s how to refresh your little black dress in style! The addition of a beige overcoat brings the ultimate fall vibes, transforming this basic black dress into a chic and sexy outfit. Pairing it with black knee-high boots and a brown handbag adds the perfect touch of sophistication. This combination of class and comfort is our favorite way to elevate any look!

CONCLUSION

The little black dress has stood the test of time, remaining a perennial fashion favorite. Its enduring appeal lies in its ability to adapt to changing trends while retaining its timeless elegance. By exploring these 15 diverse styles, we’ve witnessed the versatility and power of this iconic piece. Whether you’re a fashion-forward individual or a classic style enthusiast, the little black dress offers something for everyone. So, embrace its potential and let it become your go-to outfit for any occasion.