jackets to wear over dress shirts

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!

WHAT TO WEAR IN LONDON: A FIRST-TIMER’S PACKING GUIDE

London, a city of iconic landmarks, rich history, and vibrant culture, can also be a bit of a fashion enigma. With its unpredictable weather and a blend of classic and contemporary style, packing for your first trip can be daunting. But fear not! This guide will equip you with essential packing tips to ensure you’re stylish and comfortable throughout your London adventure. Whether you’re planning a summer stroll through Hyde Park or a winter visit to Buckingham Palace, we’ve got you covered. Let’s dive into the art of packing for London!

CURIOUS ABOUT WHAT TO WEAR IN LONDON?

Lucky you! If you’ve been following this blog for a while, you know I’m a dedicated anglophile. I’m always planning my next trip to London, and I firmly believe the British capital is the greatest city in the world. Sure, other cities might have better food, nicer weather, or fewer tourists, but, as J.K. Rowling aptly put it, you can’t beat “the history and mystery of London.” The city boasts some of the world’s greatest museums, proximity to excellent day trip destinations, vibrant nightlife, the West End, stunning hotels, historic and cutting-edge shopping, and, of course, that unique pub life.

With all that said, dressing for London as a tourist can be quite the challenge. You want to look stylish in one of the chicest cities in the world, but you’ll also be walking up to 15 miles a day, standing in long lines, and heading out for fancy meals. Plus, it could rain at any moment, often unexpectedly and for varying durations.

But don’t worry! With several trips to the U.K. under my belt, I can help ease your packing anxieties and create the perfect London packing list. So, check that weather forecast (spoiler: there’s a chance of rain), and let’s get those bags packed for an unforgettable trip to London!

REMEMBER TO BRING YOUR PACKING CUBES!

No packing guide would be complete without mentioning my secret weapon: packing cubes! They keep everything organized before, during, and after your trip. I love how they help keep small items neat and tidy in the hotel room, and they’re also perfect for packing souvenirs on your way home!

WHAT’S THE WEATHER LIKE IN LONDON?

Weather is a key factor when packing for any trip, and in London, the ever-present chance of rain often takes precedence over seasonal changes. London experiences the typical four seasons, but temperatures are generally milder compared to the extremes found in the central U.S. For example, July averages around 74°F during the day and 59°F at night, while December sees temperatures of about 48°F during the day and 40°F at night. So, while summers are warmer, they’re not excessively hot—leave the short shorts at home, as many homes and public places in the UK lack air conditioning. On the flip side, you probably won’t need that heavy Canada Goose coat in winter.

DOES IT REALLY RAIN THAT OFTEN IN LONDON?

Yes, it does rain frequently in London. While you might encounter an occasional all-day downpour, it’s more common to experience unexpected showers, often in the afternoon or at inconvenient times. Londoners seem unfazed, often carrying on with their day in wool suits as if the drizzle doesn’t bother them at all. This can put a damper on your sightseeing plans, so having a reliable umbrella and a durable rain jacket is essential. We’ll dive into more details on this later.

WHAT TO WEAR IN LONDON

A TRENCH COAT

The British trench coat is a must-have for any trip to the U.K. Burberry remains the classic choice, now offered in various shorter and more colorful styles. If you prefer a subtler look, a darker, less conspicuous trench is a great option. J.Crew also offers some stylish trench coats that are worth checking out!

A BARBOUR JACKET

Barbour, a quintessential English brand, offers a range of jackets from traditional waxed styles to lighter, quilted options. The waxed jacket is particularly waterproof and, with the addition of a hood, is ideal for a day of sightseeing. Regardless of the season, Barbour is my top choice for exploring London. You’ll enjoy the classic charm of a British brand while staying prepared for any unexpected showers.

The Queen was famously fond of her Barbour coat. When she sent it in for refurbishment—a common practice with Barbour coats, designed to last a lifetime—the company offered her a new one. She graciously declined, preferring to keep her well-loved old coat!

A FEW TOPS

Finding the right sweaters for your trip to the U.K. is essential, as the damp weather can feel chillier than it might actually be. Even if it’s not extremely cold, you’ll appreciate having cozy sweaters to keep warm, especially when enjoying classic British comforts like pubs, tea, and a Sunday roast.

Unless you’re visiting during the peak of summer, packing at least one warm sweater is a must. I prefer turtlenecks for colder months, including spring and fall, as they eliminate the need for a scarf. Brands like Eileen Fisher offer excellent options. Ensure your sweaters fit comfortably under the coat you plan to bring by trying them on together before you leave. For additional options, consider checking out Orvis, LL Bean, and J McLaughlin for dressier sweaters.

Also, pack a couple of lightweight long-sleeved shirts that can easily fit under your jacket. If you need a few nicer tops for evenings out, include them, but don’t overpack blouses. In most cases, a light sweater or long-sleeved shirt will suffice, especially if you’re spending most evenings in the pub.

FEW PAIRS OF PERFECT PANTS

A fun fact to note is that in the U.K., “pants” refers to underpants, so use “jeans” or “trousers” when talking about what Americans call “pants.” For your trip, a pair of jeans and some casual black trousers should work well. I recommend Eileen Fisher’s crepe pants for comfortable travel. As for leggings, they are acceptable in London, but make sure to pair them with a longer shirt or tunic for a polished look.

THE RIGHT SHOES

Finding the right shoes for a trip to Europe can be challenging, but it’s essential for both comfort and style. For London, I recommend packing:

Knee-High or Ankle Boots: These are versatile and great for dealing with rain and walking long distances.

Loafers: Ideal for days when the weather is milder or when you want a break from boots. I’ve found Sam Edelman loafers to be particularly comfortable and stylish.

Clean Sneakers: Opt for a pair that’s not too sporty, like Veja, which are both fashionable and comfortable.

If you’re visiting during the summer, consider bringing a pair of sandals for quick outings, but skip the beach flip-flops, as they can look out of place and get dirty quickly. For rainy months, waterproof boots or booties are a must. Riding boots offer excellent coverage and comfort, but if they’re not your style, ankle boots or lug boots can work as long as you can walk in them all day.

For those with evening plans, sticking to boots or loafers might be your best bet instead of packing high heels. And while sneakers have become more acceptable, sticking to clean, stylish options like Veja will keep you looking chic and comfortable, just like Kate Middleton.

A NOTE ON DRESS CODES…

In the U.K. and across Europe, some establishments such as upscale restaurants, clubs, and religious sites (though less so in the U.K.) may have dress codes. It’s a good idea to check the websites of any restaurants or theaters you plan to visit to confirm their policies on jeans and sneakers. Some places might also require men to wear jackets. As an everyday tourist, this is likely to be less of an issue for you, but it’s worth verifying to avoid any surprises.

​DRESSES

On sunny days in London, a dress with a light jacket and loafers is perfect for exploring the city. Europeans typically reserve beach flip flops for the beach, so opt for more appropriate footwear. Boden offers excellent dress options ideal for enjoying the weather or attending a West End show.

Even on warmer days, it’s smart to carry an umbrella, as British weather can be unpredictable. To stay prepared for occasional drizzles, choose fabrics that handle rain well and consider adding tights, leggings, a scarf, and black riding boots. This will ensure you stay cozy and stylish, regardless of the weather.

PURSES FOR LONDON

When choosing a purse for London, the most crucial feature is that it should close fully to deter pickpockets, especially at popular tourist spots and on public transport. While I found London to be less prone to pickpocketing compared to other cities, it’s still wise to avoid large, open tote bags.

Opt for a small, lightweight purse that can carry just the essentials: an umbrella, money, credit cards, your phone, and an Oyster Card. A small crossbody bag is a great choice for ease of access and security. If you prefer more space, the Longchamp Le Pliage is a classic option, even if it’s not British—it’s stylish and practical, and if it’s good enough for The Princess of Wales, it’s good enough for me! For a British touch, check out The Cambridge Satchel Co., known for its beautifully crafted, traditional handbags. I picked up a saddle bag with a long crossbody strap there, perfect for easy touring.

WINTER COAT AND UMBRELLA

When packing for London, consider that it doesn’t usually get extremely cold. If you’re short on space, you might skip a winter coat in favor of a heavy Barbour jacket. However, if you’re traveling between December and March or plan to spend time in colder regions of the U.K., including a winter coat is advisable, especially for evenings out when you might want to dress up.

Avoid bringing your nicest wool coat due to the frequent rain. If you do bring a winter coat, consider packing a trench coat as well. For rainy days, an umbrella is essential. I recommend a compact umbrella that fits into a coat pocket or a small purse for convenience. If you prefer a larger umbrella, it’s often best to buy one once you arrive or borrow one from your hotel rather than lugging it with you.

KEEPING KIDS DRY

Keeping kids dry in London’s persistent rain can be a challenge, but it’s essential for a happy trip. Invest in high-quality waterproof jackets and pants that are both practical and stylish. Don’t forget sturdy, waterproof boots to keep little feet dry. Pack plenty of layers so you can adjust to changing weather conditions. And remember, a good sense of humor and a positive attitude can go a long way in embracing the rain!

CONCLUSION

Packing for London might seem tricky, but with a little planning, you can be ready for anything the city throws your way. Remember, layers are key, and don’t forget that iconic London style often involves a mix of classic and contemporary. So, embrace the unpredictable weather, pack versatile pieces, and get ready to explore this incredible city in style. Happy travels!