try before you buy shoes

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!

HOW TO DECLUTTER & ORGANISE YOUR WARDROBE

Cleaning out your closet may seem overwhelming, especially when you have a lot of clothes to go through. However, the feeling of accomplishment once it’s done is well worth the effort. A thorough closet clean-out can transform not only how you view your wardrobe but also how you shop, while giving you a refreshed sense of style and organization. In this post, I’ll guide you through 10 practical steps to help you efficiently declutter and organize your closet for a more streamlined and satisfying space.

STEP 1 – TAKE A BEFORE PHOTO

Before you start cleaning out your closet, I highly recommend snapping a picture of your wardrobe as it looks right now. It might be tempting to skip this step—after all, who wants a visual reminder of the current chaos? But trust me, when you finish, you’ll be grateful you have that “before” shot. It will serve as a powerful reminder of how much progress you’ve made. Plus, when you’re halfway through the process and feeling like giving up, looking back at that photo can be just the motivation you need to keep pushing forward.

STEP 2 – EMPTY OUT YOUR WARDROBE

Start by taking everything out of your wardrobe. While it might seem overwhelming at first, laying all your clothes out will give you a clearer sense of just how much you have—and how much you actually use. If your wardrobe is large or space is limited, you can approach this task in sections. It’s normal for things to look worse before they improve, but don’t worry—the mess is temporary, and soon we’ll have everything neatly organized!

STEP 3 – SEPARATE EVERYTHING INTO PILES

Separate your clothes into three piles: yes, no, and maybe. Be strict but mindful during this step. For example, make sure you’re not getting rid of something you’ll end up wanting to repurchase later. This is where the ‘maybe’ pile can really come in handy.

Pro tip: Ask yourself specific questions as you sort your clothes into these piles:

  • Do I wear this item? If not, could I wear it more often?
  • Does this item fit my current style?
  • Would I buy this item today?
  • Don’t hold onto things just because they’re new—if you don’t wear it, it’s not worth keeping.

Feel free to try things on as you go. Sometimes the best way to decide if you still like something is to see how it looks and makes you feel.

For high-quality items you like but that need repairs or alterations, consider setting them aside for tailoring. I’ve done this with several pieces, and while it may seem like extra work, it’s often cheaper than replacing the item. Plus, tailoring can give new life to older pieces. For instance, I’ve had trousers and jeans taken in for a better fit, and they’ve since become some of my favorite pieces—something rarely achieved when buying off-the-rack.

If you’re still unsure about what to keep or get rid of, I’ve created a helpful flow chart to guide you through the process of deciding which items to keep, donate, or recycle.

STEP 4 – REPEAT THE SAME PROCESS FOR SHOES, BAGS AND ACCESSORIES 

You know the routine: go through the rest of your wardrobe, including shoes, bags, and accessories, and sort them into ‘yes,’ ‘no,’ and ‘maybe’ piles. Apply the same approach, being mindful of what you actually use and what aligns with your style.

STEP 5 – CREATE A SEPARATE STORAGE SPACE FOR SENTIMENTAL ITEMS

You may come across a few sentimental pieces that you really want to keep, and that’s perfectly fine—just create a designated space to store them. However, be careful not to hold onto items simply because you once loved them. If it’s something you’ll never wear again, take a moment to reflect on why you still want to keep it.

I understand that letting go of certain items can be tough, especially if you’re someone who attaches emotions and memories to clothing. I’ve been there myself, struggling to separate memories from items. But once I learned to do this, it felt incredibly freeing. What helped me let go was finding comfort in knowing the items would have a new home where they’d be appreciated. The more I decluttered, the easier it became.

I did allow myself to keep a small number of items purely for sentimental reasons. For instance, I kept my high school leaver’s shirt signed by my classmates and the dress I wore on my first date with Damien. It’s important not to throw away family heirlooms or items with real sentimental value, but try to be strict with yourself during the process. Don’t hold onto things out of a sense of obligation.

Remember, the goal is to declutter, so don’t keep things just for the sake of it. It’s okay if you can’t part with everything right away, but be mindful of what you’re holding onto and why. And if you can pass something along to someone who will love and use it just as much as you did, don’t hesitate to let it go.

STEP 6 – RE-ORGANISE YOUR ‘YES’ PILE

If you haven’t already organized your clothes by season, now is a great time to do so. This will help you avoid feeling overwhelmed by clothes you can’t currently wear. Of course, this tip may be more relevant depending on where you live. For instance, if you live somewhere like the UK, where you experience all four seasons, your wardrobe will change throughout the year based on the weather.

Set aside a specific area or create storage for out-of-season clothing or items you won’t need soon, like special occasion wear. I suggest using storage bins or boxes so you can easily tuck these items away until they’re needed again.

STEP 7 – PUT ALL THE ITEMS YOU LOVE BACK INTO YOUR WARDROBE 

Begin placing the items from your ‘yes’ pile back into your wardrobe, organizing them as you go.

Top Tip: Consider replacing mismatched or wire hangers with uniform ones for a more cohesive look. I personally prefer white wooden hangers for their sturdiness, but velvet hangers are also a great option—especially if you’re short on space or need something that holds slippery fabrics, like satin, in place.

STEP 8 – GO THROUGH YOUR ‘NO’ PILE

Go through your ‘no’ pile and decide what can be donated to friends or family, sent to a charity shop, or thrown away. When disposing of old clothes, remember it’s important to recycle them whenever possible to avoid contributing to landfills.

Now, grab your bags and start sorting unwanted clothes into categories such as:

  • Items to sell
  • Charity shop donations
  • Items for friends and family
  • Items to recycle

This will help you stay organized and ensure everything finds the right place.

STEP 9 – ASSESS YOUR ‘MAYBE’ PILE

Examine your ‘maybe’ pile and try on each piece if you haven’t done so already. Consider what you like and dislike about them. If the cons outweigh the pros, you’ll know what to do. Don’t forget to refer back to the flow chart for guidance.

If you’re still unsure about some items, avoid making hasty decisions. Instead, bag these pieces up or store them in a place that doesn’t disrupt your organized wardrobe—somewhere out of sight, like under your bed, could work well.

I recommend giving it at least a four-week period. If you find that you haven’t missed or searched for any items from the ‘maybe’ pile by the end of that time, it’s a good indication that those pieces are ready to be passed on or recycled.

Top Tip: To remind yourself to check back on your ‘maybe’ pile, set a reminder on your phone or mark it in your calendar for one month later. This will help ensure you don’t forget to revisit those items!

STEP 10 – RE-VISIT YOUR ‘MAYBE’ PILE

Now that you’ve lived with your newly decluttered wardrobe for a month, it’s time to revisit that ‘maybe’ pile you set aside. By now, you should have a clearer sense of whether to keep or part with these items. If you’re still unsure, your hesitation might stem from old sentimental attachments. Remember why you started this process and reflect on the benefits you’ve experienced since decluttering.

If you haven’t missed any items from the ‘maybe’ pile over the past four weeks, it’s time to re-home or recycle them.

You Did It!
Take a moment to celebrate your accomplishment! Snap a picture of your newly organized wardrobe and compare it to the before photo you took. This visual reminder will help you appreciate how far you’ve come and can motivate you if clutter starts to creep back in.

Hopefully, this decluttering journey has rekindled your love for your wardrobe. As you add new items in the future, you’ll be better equipped to assess what truly belongs in your space, keeping it well-organized, cherished, and clutter-free!