please advise

Ask Chris Black: What Should a Man (Well) Over 50 Buy to Update His Casual Wear?

Photo: Amardeep Singh

If you’re looking for the most powerful hair dryer or the handiest chef’s knife, those things can be easy enough to find. Other objects of desire are a little more taste-based. What’s the next status water bottle or hand wash, for instance? Chris Black (he’s a partner at brand consultancy Public Announcement) is here to help, in the form of a regular column. If you have a burning question about the next fanny pack or Noah rugby shirt, drop us an email with the subject line “Ask Chris” at

What types of clothes would you suggest to a man (well) over 50 who wants to update his casual wardrobe?

Funnily enough, I just had a long discussion about this with a friend’s dad when we ran into each other in Istanbul. Over an ice-cold bottle of Uludağ Premium Sparkling Natural Mineral Water, he explained that he never felt truly comfortable shopping, and therefore his default setting was ultracasual. I told him, as I will now tell you, stick to classics, make sure it all fits well, and swag out baby! Age ain’t nothing but a number.

Start with a pair of simple RRL five-pocket slim-fit selvedge jeans. Ralph Lauren might be the best-dressed man (well) over 50. You cannot go wrong, and with proper care, they will last forever.

This navy Sid Mashburn trench coat is filled with the leftover cashmere fuzz (!!!) collected while making sweaters. A proper trench that can also keep you warm? Brilliant and chic! If you like the look of it, Sid Mashburn also makes a less expensive nylon version that looks just as sharp.

Since the rest of your look is pretty understated, why not give it a little FLAVOR with this J.Crew cashmere sweater in a great shade of pink. If the pink is too much flavor for your taste, it comes in 13 other colors, too.

Men of a certain age often make errors with footwear when trying to seem young and hip. Some might advise Converse Chuck Taylors to complete this outfit; NOT I. I still have PTSD from when every rich older guy with a young girlfriend and a David Yurman bracelet was wearing those John Varvatos washed canvas laceless Converse. Yikes. A man of y