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

By,a style columnist at the Strategist since 2019.He is also a co-host of ‘How Long Gone’ and the founder of Done To Death Projects.
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If you’re looking for the most powerfulhair dryeror the handiestchef’s knife, those things can be easy enough to find. Other objects of desire are a little more taste-based. What’s the next statuswater bottleorhand wash, for instance? Chris Black (he’s a partner at brand consultancyPublic Announcement) is here to help, in the form ofa 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 strategist@nymag.com.

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 afriend’s dadwhen we ran into each other in Istanbul. Over an ice-cold bottle ofUludağ 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.

RRL Slim Fit Selvedge Jean
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Start with a pair of simple RRL five-pocket slim-fit selvedgejeans. 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 Cashball Traveler’s Trench
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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 alsomakes a less expensive nylon version that looks just as sharp.

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

Church’s McFarlane Boot
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Men of a certain age often make errors withfootwearwhen trying to seemyoung and hip. Some might adviseConverse Chuck Taylorsto 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 ofproper shoes. These Church’s brogue boots are elegant but outfitted with a big-boy shitkicker commando sole. Suitable for all occasions.

Oliver Peoples Grey Sheldrake Sunglasses
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Top it off with a tonal gray pair ofsunglassesfrom Oliver Peoples. Perfect for leaving that power lunch at La Scala. No one will ask for your AARP Card, I promise.

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

Baccarat Harmonie Tumbler, Set of 2
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I hope your friends and relatives have good taste! I agree a $60 bottle of Veuve isn’t unique. But if the birthday girl/boy loves the sauce,get them a proper vesselto enjoy it from. A set of two Baccarat Clear crystal Harmonie tumblers will make any spirit taste better.

Raawii Strøm Large Bowl
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Something for the homeis 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.

iittala Aalto Vase, Large
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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.

Mark Leckey, Fiorucci Made Me Hardcore, at Tate Britain, 2019
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It’s always nice to receive aprintor exhibitionposterfrom 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 current exhibition at the Tate Britain. Anyway, pick something appropriate, send it toFramebridge, and make someone so happy that they forget they are turning 30. [New Found Glory voice:] “Cause it’s all downhill from here…” [Editor’s note: The price below has been converted from British pounds.]

What do you look for in awinter 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 andcolors. Let’s … explore.

Burberry Fringed Checked Cashmere Scarf
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My No. 1 suggestion has got to be the classic Burberry check. A timeless scarf that will instantly give you that’70s and ’80s “Sloane Ranger” style. I owned one of these during my party days and left it in a booth at some disgusting bar below 14th Street. It might be time to buy another one.

Missoni Space-Dyed Cashmere and Wool Blend Scarf
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Let’sgo to Mars! Missoni added its signature space-dyed stripes to this simple navy cashmere-and-wool blend. Just the right amount of pop.

Barbour Fringed Tartan Scarf
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If you want to keep it preppy, classic,andaffordable, cop this tartan merino-cashmere blend from Barbour. Maybe it will help you attract thathorse girlyou have been lusting after.

The Strategistis designed to surface the most useful, expert recommendations for things to buy across the vast e-commerce landscape. Some of our latest conquests include the bestacne treatments,rolling luggage,pillows for side sleepers,natural anxiety remedies, andbath towels. We update links when possible, but note that deals can expire and all prices are subject to change.

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