Chris Black has returned to the Strategist with a monthly column to answer all of your burning questions — from super-specific style predicaments and workout and tennis recs to foolproof host-gift ideas that will get you invited back to the beach house.
Where am I supposed to keep my keys? I’m done with carabiners!
We are all done with carabiners. Men everywhere have been walking around with keys jingling, performing art-handler cosplay for too long. Buy a nice keychain and put the keys in your pocket where they belong. The piece of metal you use to unlock the door is not an accessory. A nice keychain also makes the perfect gift. The holidays are fast approaching!
I love the look of this, but it is a little puffy. It will probably work better in a bag, but you can’t go wrong either way. The brown is subtle.
I have two of these, one in brown and one in dark blue. The classic Bottega braided leather never goes out of style. It fits comfortably in my back pocket or bag and can take a beating. They look better with age. Highly recommended.
This is so simple and understated — just black leather with a sturdy snap. This can be hooked on your belt loop, but please, just put it in your pocket and keep it moving.
I have given several Various Keytags as gifts over the years. They are simple and fully customizable in a nice range of colors, and the packaging is clever. This does force you to get creative, but I have faith.
Suggestions for a premium tote bag?
The cheap and ubiquitous tote you received free with a magazine subscription is probably worn out, having sat on too many Brooklyn coffee shop floors while you pecked away at your laptop. It’s time for an upgrade, something a little nicer, and maybe more durable materials.
Steele makes some of the highest-quality tote bags in the world. The thick canvas will last forever, and the straps are durable and long enough to go over the shoulder. Think of it as a heavy-duty version of the classic L.L. Bean.
Leather tote bags are just expensive. That’s how it goes. They feel more upmarket and age a little more gracefully than their canvas brethren. This one from Jil Sander has handles and a crossbody strap, which makes it great for travel or the office.
If you want something less understated, Pacific Tote Company has you covered. This open-top canvas tote comes in an eclectic shade of orange that will have heads turning.
The A.P.C. JW Anderson collaborative collection was quite good, but the tote bag stood out. Done in a great shade of deep blue, it features a heavy-duty co-branded two-way zipper to keep your stuff secure.
Best cashmere sweaters?
Once it finally gets cold, nothing is more necessary than a cashmere sweater. Warm, versatile, and appropriate for any situation. The price range in this category is insane, but I think I show options from every category below. If you want Loro Piana, go to eBay.
Isn’t this a great color? The perfect shade of rose in a simple cashmere crewneck from Australia’s P. Johnson. Sure it’s not as practical as navy, black, or even camel, but it is a lot more fun.
[Editor’s note: P. Johnson lists its prices in AUD; the price listed is an approximation.]
I own several Uniqlo cashmere sweaters. The fit is good, and the price is unbeatable. This shade of green I haven’t seen before, but I love it.
Mr. Porter’s in-house brand, Mr. P, is criminally underrated. They consistently churn out great simple garments, and this cashmere navy polo shirt is no exception. I guess this is technically not a sweater, but I think it is just as wearable and can serve the same purpose as a classic crewneck version.
This is a classic crewneck sweatshirt shape (raglan sleeves and all) done in cashmere for added warmth. I love how casual it feels. It could work in the office, but feels even more appropriate for the weekend.
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