Men’s Shoes Over 50

This chick’s picks for fab footwear. Looking for the best men's shoes for all occasions? Sheri Radel Rosenberg has you covered.

One of my favorite pieces I have ever written was about men’s shoes. LL Bean boots, in particular.

I opined how hot it is for a man to wear duck boots because it speaks to a preppy ruggedness that I have always found extremely attractive.  But WASP envy aside, you can tell a lot about a man by the shoes he wears, and when it comes to style, size doesn’t matter. So when I was asked to pen a shoe story,  I didn’t hesitate.

Fact: women talk about and shop for shoes like nobody’s business. Saks in NY has a shoe floor that boasts its own zip code; it’s so large. But as we get older, our relationship with shoes truly changes. Because as much as we love the latest shoe, we secretly thank our stars that most of the shoes du jour are built for comfort. Take the current fixation on the Boston style of the Birkenstock. Both men and women are clamoring for it, and though it entirely reminds me of a Nutter Butter, I’m down with it, particularly on a particular type of man. I’d say tall, lanky, and sort of Bourdain-like is the proper brief. That or a blonde surfer dude. Otherwise, it could get very Tolkien. I’m guessing most men don’t want to look elfen so take that with a fine grain of salt.

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So what is suitable for guys past 50, then?

It depends on your lifestyle, work style, and, most of all, comfort zone. And by that, I mean your cushy, happy, comfy place where your feet don’t hurt, and life’s too short to wear painful shoes.

The sneaker

My 52-year-old husband always wears classic Nike Jordans and loves the original look like these here. We live in New York City, and these feel just right for an urban lifestyle.  The founder of this publication is a fan of the Nike Tailwind 79, which is sleek, versatile, and very comfortable. I also am a personal fan of a Converse Jack Purcell in the warmer months because they are classic and somewhat rebellious at once. And a guy who wears Stan Smiths always looks confident and cool. They are such an iconic kick that you can’t go wrong with them. 

Nike Jordan 1
Nike Jordan 1.
Nike Tailwind 79
Nike Tailwind 79.
Converse Jack Purcell
Converse Jack Purcell.
Adidas Stan Smith
Adidas Stan Smith.

The desert boot

If you feel like sneakers are past due for you besides in the gym, may I offer up the desert boot?

I wrote about these a few weeks back and stand by their laid-back but put-together appeal. Pop these on with anything from jeans to a suit. A desert boot has youthful coolness that works well for a mature moment in life. To me, they say “comfortable in my own skin or feet.” These are good, too.

Todd Snyder Nomad Boot
Todd Snyder Nomad Boot.
J.Crew MacAlister Boot.
J.Crew MacAlister Boot.

The Chelsea boot

This is one of my favorite boots for dudes because they are rock and roll sexy at their best. I love them with black jeans and a blazer with a button-down. This Saint Laurent take is the ultimate, in my opinion, but there are lower-priced options to be had like these from Zara.

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Saint Laurent Wyatt Chelsea Boots
Saint Laurent Wyatt Chelsea Boots.
Zara Chelsea Boots
Zara Chelsea Boots.

The cold weather boot

And when it comes to boots, you can’t go wrong with a classic hiking boot; whether indoorsy or outdoorsy, they work well for “heartier” climates, aka cold weather. Here at AGEIST, we love the Aether varietal, and I prefer the moto lace up to the alpine boot, but you do you. This boot from Rag and Bone is also quite good, wearable, and more grown-up than a Doc Marten. Don’t hate me. A more affordable take like these from Thursday Boot Co.

Aether Dolomite Boot.
Aether Dolomite Boot.
Rag & Bone Grenson Dodger Boot.
Rag & Bone Grenson Dodger Boot.
Thursday Boot Co. Caption Boot.
Thursday Boot Co. Caption Boot.

The dress shoe

Now let’s chat about dress shoes because they’re tough (too pointy, too shiny, too cheesy). 

Much like women, many men don’t have to dress for work anymore. The Don Draper era is long gone, and daily suit wear is the provenance of a very rare few. But if you wear a suit from time to time, a good lace-up is your BFF. We suggest something classic and admittedly spendy, like the Prada version. They look equally cool with a cuffed selvedge jean as they do with a suit, so that’s a win-win. One shoe that I don’t like? A monk strap. Don’t like. Never have. Never will. 

Prada Brushed Leather Oxford Shoes.
Prada Brushed Leather Oxford Shoes.

The loafer

I also am noticing an uptick in men wearing loafers in that classic Weejun silhouette that may remind one of “Happy Days” but are worth a rethink. I recently popped into the gorgeous new J. Press store in midtown and all the guys working there were rocking a stiff, shiny black loafer, and they all looked so amazing (it’s my preppy thing again). If it all feels too Yale Club, check out this take from Paraboot. I love them with khakis, rolled-up jeans, and a suit.

Paraboot Columbia Loafer.
Paraboot Columbia Loafer.

The sandal

Tough one.  As a rule, mandals bug me. If you must, go for the Birkenstock Arizona or a simple flip-flop like these while beach or poolside. That is all I have to say on the subject. Next.

Havaianas Brazil Flip Flop.
Havaianas Brazil Flip Flop.

Regardless of your style or stage in life, shoes do indeed make the man. But so does a sense of humor, strong character, and confidence. That’s my take. And should you want to check out my poetic wax on the LL Bean duck boot, the post is here. It still makes me smile, so let’s hear it for the boys. Of course, never stop wearing your slip-on Vans. They’re the kick back, summer equivalent of my beloved duck boots. And yes, you may have worn them in high school or college, but they are transcendent enough to have ageless, effortless appeal. 

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Vans Classic Slip On.
Vans Classic Slip On.
See medical disclaimer below. ↓


  1. Well I am with you on almost all your choices except I would rather see men in top siders than flip flops over the age of 35. Ugh and men get pedicures….no polish but cut those toe nails if you are going to expose them. I always bought my son Cole Hahn loafers – my favorite. Did you forget them? Loafers are very cool no matter what a man is wearing. The first thing I look at in a man is his shoes as I figure any good salesperson can dress them well down to their ankles and then the guy is left on his own…and this is wear his own personal taste kicks in , so it’s telling. Dress shoes are the hardest and usually dislike most of them. Iffy on the Chelea boot. I hope men take a good hard look at your choices!!! Good job

  2. Ageless style, stepping into a new era These men’s shoes redefine fashion with a mature charm. From timeless loafers to classic oxfords, they embrace sophistication and comfort for the distinguished man. With every step, experience the perfect blend of style and maturity. Celebrate the journey with the best footwear options for men over 50, where fashion becomes a reflection of wisdom and enduring elegance. Step into the next chapter with shoes that age as gracefully as you do


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The ideas expressed here are solely the opinions of the author and are not researched or verified by AGEIST LLC, or anyone associated with AGEIST LLC. This material should not be construed as medical advice or recommendation, it is for informational use only. We encourage all readers to discuss with your qualified practitioners the relevance of the application of any of these ideas to your life. The recommendations contained herein are not intended to diagnose, treat, cure or prevent any disease. You should always consult your physician or other qualified health provider before starting any new treatment or stopping any treatment that has been prescribed for you by your physician or other qualified health provider. Please call your doctor or 911 immediately if you think you may have a medical or psychiatric emergency.

Sheri Radel Rosenberghttps://unapologeticstyle.substack.com/
Sheri Radel Rosenberg is a Philly-born, Brooklyn-based writer who explores style, beauty, culture, and midlife with wit, warmth, and wisdom. Her story includes successful forays in the worlds of trend forecasting, ad agency photo production, ghostwriting, and strategic messaging development for fashion and beauty brands - all while amassing a slip dress collection that would make any Gen Xer proud. At the dawn of social media, Sheri launched her personal blog–which combines her passion for writing with her style obsession–and she hasn’t looked back. As Style Editor for the AGEIST, she’s inspired by the styles of the 70s and the 90s, along with all the beautiful people she sees daily in NYC.


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