7 Tips to Know Before You Shop

By Caroline Reilly | Last Updated: Jul 7 2022

As Team SG’s resident dad style-whisperer, there’s nothing I love more than helping a mature male styling client fall in love with clothes.

It’s especially satisfying dealing in fashion for men over 50.

Figuring out how to dress in your 50s (and beyond!) can feel like a challenge, but I’m here to tell you it’s totally doable. And since I cannot personally counsel every guy out there finding an AARP membership in waiting in his mailbox, the next best thing is this—a definitive guide to dressing for mature men. 

Now, if you’re new here, you might be wondering: Caroline, you’re a 29-year-old woman whose primary hobbies include watching Nordic crime shows and perfecting homemade macaroni and cheese. What could you possibly know about the style trials and tribulations of a man closing in on early retirement? 

Well for starters, I love a well-dressed older man.

My first crush was the Professor on Gilligan’s Island! To this day, my hall pass remains Senator Sheldon Whitehouse of Rhode Island (if you’re reading this, Shelly, let me help you pick some new ties!) 

Beyond that, I’ve done the work. I’ve interviewed some of the most renowned costume designers, tailors, and stylists about style for men over 50. 

The woman who dresses Larry David? She told me all his must-have items. The tailor who makes the suits for the cast of Billions? He shared the tips and tricks those guys use to look their best. I even spent two months interviewing male supermodels over 50 about what style means to them. 

…I know, it’s a tough job, but someone’s got to do it!

Any time I watch a show or a movie my eyes are trained on what the older men are wearing. How are their clothes tailored? What colors complement their grey hair? 

But here’s the thing. Age really is just a number. Maybe your hair has gone grey or you’ve lost it completely. Or your body doesn’t look the way it did when you were in college—honestly, it would be crazy if it did—but I bet you’re not sleeping on a mattress on the floor anymore, either! 

Bottom line?

Growing older doesn’t need to make you less fashionable, or less cool. 

And look, what a man over 50 needs in his wardrobe changes by the guy. Maybe you’re looking for casual clothes for older men, or want to know where to shop in your 50’s. Fashion for older guys can be as fun and varied as clothing for guys in their 20’s. 

Don’t know where to start? Don’t worry.

Here are my top tips on mature style for men:

1. Get a tailor

Every single person I’ve spoken to who works in style for men over 50 (and men in general for that matter) says one of the main things that distinguishes “a guy wearing clothes” from a “well-dressed man” is good tailoring. 

Building a relationship with a tailor is a really important part of being a well-dressed mature man.

So, think about your tailor like a doctor for your clothes. You have a dentist to take care of your teeth, an internist to check your blood pressure, a dermatologist to check out that weird mole on your back. It’s time to get a tailor on call to make sure your wardrobe is in good health, too. 

And I know what you’re thinking: the clothes I own fits me just fine! 

Well, not quite. 

No man – and I mean not a single one of you – fits into clothing perfectly off the rack.

And no, you don’t need to have your t-shirts tailored, or all your sweatpants hemmed – but the sleeves on those button downs you wear everyday with jeans or chinos? Have them tailored to the right length. 

And those jeans and chinos, too! 

Or how about the blazer you wear to dinner with your spouse every week? Could you have it taken in or let out to fit you just a little bit better? 

RELATED: Wardrobe Essentials for your 50s

Again, think about it like going to the doctor – you don’t go every single day for every little thing that goes wrong, but the big things? You want to bring in a professional. 

2. Target personal style, not trends

Here’s a secret: this is also advice I give my younger clients–but older guys especially look their best when they dress for who they are and not to keep up with the latest and greatest trends. 

By midlife, you’ve seen a lot of trends go in and out of fashion. This just means it will be that much easier to figure out what cut trouser looks best on you and what colors and textures complement your aesthetic.

Like, what kind of clothing best suits your lifestyle, and what pieces don’t really make sense for a guy like you.  (And if you’ve still got questions, you can sign up for a styling session with yours truly, or another member of Team SG here.) 

Try not to think about this guideline as limiting. After all, every guy, whether he’s a buff 20-year-old or a first-time grandfather, can think of clothes that make him look his best, and clothes that don’t look quite right on him. 

Instead, consider this permission slip to to skip trends as a luxury! 

As men age, they get more distinguished – the nickname“silver fox” is a compliment for a reason. 

Allyson B. Fanger, the costume designer for Netflix’s Grace and Frankie, told me that one of the joys of dressing older characters like Robert and Sol, played by Martin Sheen and Sam Waterston, respectively (both 81!), is that these are men who have lived a lot of life.

The show follows two lawyers who leave their wives for one another after their kids are grown, and their style? It’s on point.

Robert and Sol aren’t evolving any further in their style, and Fanger told me that’s what makes dressing them so enjoyable.

The two characters have their favorite brands, their go-to color palettes, and they know how to find clothing that makes them feel like themselves because they really know who that is. 

Robert is traditional; he likes his button downs and his chinos – he’s a Brooks Brothers guy through and through.

Sol, on the other hand, is a hippie at heart. He loves his Cubavera camp shirts and his comfy Tommy Bahama linen pants.

The two are actually a perfect example of how, no matter what your taste is, no matter what your style – there is a way to pull off top-notch personal style at any age.  

Knowing who you are and being confident in that is the most important part of any man’s style and it’s a lot easier to achieve when you’ve spent decades learning about yourself. 

3. Invest in forever pieces

Forego fleeting trends and you can invest more money in your clothing. Why? Because you know you’re going to wear whatever you buy for longer than just one season. 

This means, instead of buying a bunch of inexpensive shirts and trousers, buy one or two of each staple item for your wardrobe. Then, have those items tailored to perfection. The last step? Embrace the ease and simplicity of having a signature personal style! 

Look for brands that put a premium on craftsmanship and quality.

You might not have the liquid cash to splurge on every item in your closet, so be strategic about where you spend your money.

Think about the items you spend the most time in. If you only occasionally wear sweaters but live in blazers, like a post-presidential Barack Obama, prioritize accordingly when you’re budgeting. 

4. Adopt a wardrobe uniform

Larry David, 75, is a big fan of uniform dressing. We often think about uniformed dressing for men as the traditional suit and tie but Larry is a great example of how versatile uniformed dressing can be.

He’s a casualwear king – in fact, if you are on the hunt for casual clothing for men over 50, the Curb Your Enthusiasm star offers a great blueprint. His go-to wardrobe staples consist of crewneck sweaters and zip ups, AG 5-pocket chinos, and soft shoulder blazers. 

If you’re the kind of guy who gets overwhelmed at the thought of picking out outfits every single day, you’re a great candidate for this approach to dressing. 

Build a capsule wardrobe with a few pieces that you love. Your favorite pants, a few shirts that make you feel your best, some knitwear or a jacket. 

And don’t be afraid to buy items you love in multiple colors! (This is something else David does.)

This way, every morning you can reach in your closet and know whatever you grab will likely go together.  

5. Lean into a Monochromatic Color Palette 

Monochromatic dressing involves pairing pieces that are all in the same color family to create a cohesive look. Dressing this way elongates your body and keeps you looking sleek, modern, and put together with minimal effort. 

If you watch Only Murders in the Building, the character Steve Martin, 76, plays is often rocking a monochromatic ensemble. Blue jeans a white shirt, with a blue knit sweater or overcoat. 

Easy to put together, even easier to look like a million bucks wearing.

You can do monochromatic a few ways, but our favorite here at team SG is to go the black and blue route – stick to saturated deep blues like navy – or the earth tones look, like tan chinos with a chunky oatmeal rollneck sweater. 

6. Focus on the finishing touches 

When it comes to presentation one of the things that separates the men from the boys is that extra attention to detail that you might not notice right away, but that makes all the difference once you do. 

I’m talking about things like a groomed beard (and nose hairs,) clean nails and cuticles, making sure you smell good. 

Then there are the accessories. A beautiful scarf can elevate a simple blue overcoat. T – the right (or wrong!) shoes can make or break a whole outfit. Accessories are also a great place to invest; you’ll never grow out of a timeless pair of glasses and if you spend money on pieces that are built to last, you’ll wear them for years to come. 

I want to give a special shoutout to timepieces: it’s one of the first things I notice about a man, if he’s wearing one, and if he is, what is it. You don’t have to break the bank here, though if you’ve got the cash for it, few items are worth investing in like a good timepiece. Even a tank style-Seiko will make you look that much more polished and distinguished.

7. Be yourself 

I know it seems silly at the end of a list of style rules to be like, oh and by the way just accept you for you! Because you might be like, well, me is a ripped sports jersey and Crocs. To which I reply: okay, change yourself, please. (I kid.) (Or do I?) 

But what I actually mean is, don’t get too in your head about dressing for a certain age. These style tips are great if you feel like you don’t know where to start, or want to improve your style game, but if you’re someone who’s already got a signature look or you like dressing outside the box, don’t ever for a second feel like you can’t because there’s a 5, 6 or 7 in front of your age. 

The best way to be well-dressed is to show up as the best version of the man you actually are. As we’ve established, getting older just means you know who that is a little more with every passing year. 

Take male model Lono Brazil, above. Brazil is dominating the mature model game right now and he’s the furthest thing from a Larry David dupe or a Brooks Brothers dad when he’s out and about. He loves to rock architectural and avante garde pieces from top designers. And it works, you know why? Because that’s who he is. 

So dress for you you are, and you’ll always be in style. 

Where to shop for clothes in your 50s

Below, check out a few of the brands I often pull for my clients who are looking for better style for men over 50: