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.

Sid Mashburn’s 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! Sid Mashburn also makes a less expensive nylon version that looks just as sharp. [Editor’s note: This price doesn’t include shipping fees.]

Since the rest of your look is pretty understated, why not give it a little FLAVOUR with this J.Crew cashmere sweater in a great shade of pink. If the pink is too much flavour for your taste, it comes in 13 other colours, 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 your stature should wear a pair of proper shoes. These Church’s brogue boots are elegant but outfitted with a big-boy shit-kicker commando sole. Suitable for all occasions.

Top it off with a tonal gray pair of sunglasses from Oliver Peoples. Perfect for leaving that power lunch at La Scala. No one will ask for your bus pass, I promise.

A handful of my friends and relatives are turning 30 over the next few months. I need to get gifts for each and want them to be slightly more special than your normal knick-knack or bottle of Veuve. Any ideas?

I hope your friends and relatives have good taste! I agree a £45 bottle of Veuve isn’t unique. But if the birthday girl/boy loves the sauce, get them a proper vessel to enjoy it from. A set of two Baccarat Clear crystal Harmonie tumblers will make any spirit taste better.

Something for the home is always nice. This sculptural Strøm Bowl from Raawii comes in a myriad of colors (I am partial to coral blush and vibrant orange) that would make anyone happy.

In that same vein, you cannot go wrong with a clear Aalto Vase. Introduced in 1937 at the World’s Fair, the wild shape is iconic and looks great in most settings.

It’s always nice to receive a print or exhibition poster from an artist you like. I would love it if someone gave me this “Mark Leckey, Fiorucci Made Me Hardcore” limited-edition signed print from Leckey’s exhibition at the Tate Britain. Anyway, pick something appropriate, get it framed, and make someone so happy that they forget they are turning 30. [New Found Glory voice: “Cause it’s all downhill from here …”]

What do you look for in a winter scarf? I’m interested in something simple but cozy.

Cashmere, baby. I only want luxe fabrics touching my sensitive neck. But, a scarf is also an excellent opportunity to get a little funky, an easy way to play with prints and colours. Let’s … explore.

Let’s go to Mars! Missoni added its signature space-dyed stripes to this simple navy cashmere-and-wool blend. Just the right amount of pop.

If you want to keep it preppy, classic, and affordable, cop this tartan merino-cashmere blend from Barbour. Maybe it will help you attract that horse girl you have been lusting after.

A version of this story originally appeared on the Strategist US.

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Ask Chris: What Casual Wear Should a Man Over 50 Be Buying?