My friend Gary Jewkes always looks “put together.” He’s retired but active in a wide variety of extended family gatherings, community book clubs, political interest groups and advocacy organizations. He doesn’t wear expensive clothes, but somehow he always seems to dress just right for every occasion.
He could write the book on dressing for success after 70. I asked him about it recently.
“It’s not about impressing anyone,” he said. “It is about being taken seriously. At our age, we already have at least one strike against us. Ageism is subtle, but it is everywhere.”
“I’m not ready to dress like a twentysomething just to be taken seriously,” I said.
“If you dress that way, you definitely won’t be taken seriously,” he replied. “What Stanley Tucci, who plays Nigel in ‘The Devil Wears Prada,’ calls dressing ‘like a kid’ is a sure way to be seen as disconnected from reality and thereby dismissed.

“It’s not about wearing expensive clothes; it’s about having clothes that fit,” he explained. “It’s not about looking younger but instead about playing the part of the seasoned travelers that we are by evoking a little gravitas.”
“Yeah, well, lots of things don’t fit anymore,” I replied. “These jeans are holding on to who I was yesterday. Sadly, I’ve outgrown them overnight!”
“They can seemingly ‘shrink’ by the hour,” he said laughingly. “But wearing clothes that don’t fit are like saying: ‘Call me Mr. Irrelevant.’”
“My grandson told me I looked vintage,” I said. “I told him I’m not vintage, I’m just hard to replace. I don’t wear Prada; I wear history.”
“I think the conversation for men in our age demographic needs to shift from ‘fitting in’ to ‘commanding the room,’” he said. “If we are going to be ‘seen,’ as younger people like to say these days, we need to look like we have something to say that is timely — maybe even timeless — rather than giving comments or wearing clothes that are tardy or out of touch. Like it or not, our clothes will speak for us before we can get a word out ourselves.”

“So what makes a difference?” I asked him. “What are your rules for old guys like us who don’t want to be ignored right off the bat?”
Here are his seven rules for sensible seniors:
- Avoid graphic tees. Don’t broadcast where you’ve been or who you voted for. Save that for later discussions.
- Get rid of baggy pants and oversized shirts that hang like tents and look like a shapeless silhouette. Form, fit and function matter more than fashion or fleeting trends.
- Match belt and shoes. This is a tried-and-true measure of being either with it or behind the times.
- Use a steamer to remove wrinkles in shirts and pants or risk being called “Rumplestiltskin.”
- Wear polos with solid colors made from fabrics like pima or Supima cotton or merino wool knits.
- Dump the sweatpants. Nothing says “I just rolled out of bed” like workout clothes all day.
- Have a few distinctive finishing touches. A watch, a lapel pin, eyewear, pocket squares or striking footwear can let others know that you pay attention to details — and that you are a force to be reckoned with, not dismissed.
Wearing appropriate clothing for any occasion can be facilitated by addressing three helpful questions:
- Does this fit my body now?
- Does this fit my lifestyle today?
- Does what I’m wearing help me “meet the moment”?
The bottom line is that people respond better to older men not when they are wearing expensive clothes but when their clothes are aligned with their identity: considered, calibrated and curated.
