Men's fashion expert Jon Simon of Paul Simon Co.

Second-generation clothier Jon Simon of Paul Simon Co. at the Village at South Park is a men's fashion expert. He has a hand in shaping the style of some of Charlotte's best-dressed men of all ages, but here he shares his advice for men 50 and up in a Q&A with The O Report.

What are some of the fashion problems men in their 50, 60, 70s and up are facing? And what are the clothing solutions you recommend?

"The business environment has become much more casual, and senior leaders are having a hard time visually distinguishing themselves. Knit shirts and khakis look good on a younger toned guy, but do not always flatter an older physique. Men this age don’t have the same body they had when they were in their 20s and now they have to turn to clothes to continue to look young and vibrant. The pace of men’s fashion is now moving more quickly than it used to and men in a leadership position need to keep in step. My suggestion is to make your clothes a priority each year. Keep up with what your needs are. Ask your significant other if they will share some of the yearly clothing budget. Find a professional to help you that you trust and are comfortable with."

What are some of the new trends that can help men in that age group update their look?

"I still believe that a sport coat is a difference maker. The shoulders and silhouette of a jacket show superiority, confidence, and give a sense of personal presence. Fabrics with stretch that started in women’s wear have invaded better men’s fashion. It has been helpful having fabrics with stretch coincide with the trimmer fits of today. This has allowed men 50 and up to adopt some trendier looks while retaining a comfortable feel."

What are the key quality wardrobe pieces that men should have by that age?

"A tuxedo for special occasions, life cycle events and galas. Two suits that are current in fit and design. A navy blazer without brass buttons. A nice piece of outerwear for wearing with nice clothes to work or going out in the evening that is in addition to their technical North Face type outerwear. Some ties that are a current width. Two good pairs of jeans, one for hanging out with the kids or grandkids on the weekend and one that is dressier for going out in the evening. And at least one sport coat that is seasonal in fabric and color."

What are your thoughts about untucked shirts?

"Untucked is comfortable, but is not flattering on all body types. There is a time and place for the look. Not all shirts are designed to be worn untucked. A professional can help you determine if the untucked look is right for you or not."

Who are the best-dressed male celebrities, from both the present and the past, that older men can look up to as style role models?

"Michael Douglas, George Clooney, Robert Redford, Tom Brady, Van Jones, Jeremy Piven and Ed Bradley."

How can men dress casually without being sloppy?

"You must have clothes that you feel comfortable and confident in. Get rid of the baggy look. Everything has a more tailored fit today. Make sure you have the right accessories. For example, wearing an old belt with a new outfit will ruin the entire look."

Trask Chukka Boots come in a variety of colors and materials including leather and suede.

What are some of your favorite new pieces for Fall/Winter that would be a great addition to the 50 and up man's wardrobe?

A quilted vest from the Italian brand Waterville.

"Trask Chuka Boots. An updated cardigan knit. An unconstructed soft coat. Five-pocket non-denim pants from Brax. New denim washes from 34 Heritage. A quilted vest from Waterville or Corneliani."