Let’s Talk About Men’s Fashion for Fall

Sheri Radel Rosenberg speaks about happiness, essential pieces, and truth with a men's style expert.

For those on the East Coast, fall has always felt like a crunchy, sepia-toned gift after an oppressive summer. And though many people I know are strictly summer folks, fall has always been my favorite time of year. I love the air, the buzz in the city on the weekends when everyone is back in town, and the kids sitting on their stoops posing for their first-day-of-school photos. I love the fall holidays and foods and the inevitable switch from iced cold brew to warm lattes. Plus, fall colors suit me best, as do fall clothes. My ultimate fall poster woman is Ali MacGraw in Love Story or Carolyn Bessette Kennedy walking through Tribeca in a long skirt and sweater. There’s a class that comes with the season. A beautiful coat. Rich colors. Turtlenecks and scarves. Boots. I love it all. 

And it’s not just women who get to switch things up for the season; men, too. My husband loves “hoodie season” and can’t wait to warm up in something comfortable and relaxed. So as we ponder a new season, I asked one of the most stylish men I know, Alex Young, Chief of Haberdashery at menswear brand Todd Snyder, who helped design David’s custom suit he had made for weddings this past summer and is now a friend of ours. I love his insights on men and style, in general.

Dressing at a certain age is simply finding the best options that just make you feel good

When I asked him about what’s important when it comes to wardrobing yourself past 50, he noted that fit, timelessness, and a general sense of comfort in your environment (and own skin) is what counts. For him, clothing is “giving a vocabulary and guidance” to feel happy because, after all, style is about happiness. As a man, finding your happy place is feeling confident and, as we get older, we know that place, because we’ve been through it all and tested the limits (you never really were a hat guy anyway) and dressing at a certain age is simply finding the best options that just make you feel good. For Alex, that’s classic with a bit of a twist, as is true to his British sensibilities. 

And though it’s true that men’s fashion can be about trends the way women’s fashion is, it’s more about “the psychology of your personality and how to dress your body with an element of taste and connected confidence as we age.” In terms of trends, he did note a loosening up of pants for men which we both agree is a welcome change. My husband just purchased these and they look so fresh. And when it comes to suiting, mohair blends are historically lovely for cooler weather and add texture, durability and function while being stylish and unique and, ultimately, not trying too hard. And as a woman, I’m here to tell you there’s nothing sexier than quiet confidence

And with that, here are his picks for the key pieces men should have as the leaves begin to fall:

The soft-shoulder sport coat. Even though we are in a way-casual moment of time, a good sport coat will always be chic and work with everything in your wardrobe. This Italian wool blazer has a relaxed yet dressed up vibe that just works and as Alex says, you can “make it a part of your life.” Not too bold. Just right. He loves the navy blue and suggests wearing with jeans or trousers. I also love the navy pinstripe for a bit more sartorial splendor.

The tweed blazer. Classic. Timeless. A little bit Robert Redford and a little bit Savile Row. The tweed blazer has been around for generations and is perfectly masculine. Alex suggests pairing it with shades of blue and putting a hoodie underneath to “take away the strictness” and make it more casual. And gray tweed is as ubiquitous to cool weather as a single malt.

The wool scarf. I’ll never forget being in Paris for my 40th and seeing all the men and women rock scarves in such cool ways. A thick wool scarf adds class, warmth, and intellectual texture. Alex loves a Drake’s version, and I myself love this green color. Add it to that tweed blazer with a pair of jeans and a button down and, instantly, you look cooler than most. 

The perfect high-end hoodie. Wearing a hoodie is like wearing a blanket.  This soft cotton Champion hoodie is so perfect for a Sunday drive in September.  I dig the army green but that baby blue is gorgeous; just consider your skin tone and what looks best. Accessible luxury at its finest. 

The suede jacket. Having shopped at Todd for a while now, I can say this is the piece I would want to wear as much as any man would. The Dylan jacket in suede is hands down the most versatile, luxe, mature-with-an-edge piece that’s a super-flattering must have. It comes in different colors like blue, rust, navy, and cappuccino as well as different fabrics, but we both agreed that the classic black suede is eternally cool and perfect on all skin tones. To me, this jacket is something you’ll look forward to putting on year after year.

The classic jean. It’s not shocking that Alex’s denim of choice is a vintage Levi’s 501. If there is any element of story to style, jeans say it all; and they should have a life and get beaten up and lived in to take us wherever we need to go. He also notes that high/low is key to mixing up your wardrobe. A pair of relatively inexpensive jeans with a more sumptuous piece like a blazer or suede jacket is what true style is all about. 

The desert boot. If a male shoe can have some sex appeal for its understated coolness, it’s the desert boot/chukka. I love how it’s age appropriate and a step past a sneaker and a step before a dress shoe. It’s all about that quiet confidence from head to toe, and these wear well with everything from casual pants to jeans to a suit. Alex’s pick is this classic, sandy tan if you only buy one pair, but the green is also good for a bit of a twist.

As a man, if you’re wondering what works wardrobe-wise as we age, I leave you with this wonderful quote from my new men’s style Jedi, Alex, and that is: “As you get older, your story becomes more complicated and detailed and interesting. Your clothing should reflect that and tell a real truth about yourself.” Amen to that, and welcome to fall. 

To connect with Alex about having something made to measure, drop him a line at alex@toddsnyder.com

See medical disclaimer below. ↓


  1. I don’t know any men that dress like this but wish I did. Everyone in New York dresses better than the rest of the country. I like the hoodie under the sport jacket and the inverted pleats are very cool. Where are these men?


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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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