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’ll get you invited back to the beach house.
What are some recommendations for affordable-ish jeans?
An age-old question. Longtime readers and known haters will expect me to suggest Levi’s 501s or maybe 505s, but I will resist. Instead, we will dive into new territory today. For years, I have seen people on Twitter denouncing denim, saying, “It’s over.” Boy, are they wrong.
I bought a vintage pair of these on a whim years ago and was very impressed with the fit and quality. No frills, well-priced, and they come in a handful of washes to fit your every mood.
I would never recommend an adult man go out in public with a Supreme logo showing, but understated and well-priced denim is a different story. This 14-ounce stone-washed version is the perfect color, and for this price, you can also get the black to round out your closet.
Sunflower is a design collective from Copenhagen that is pumping out supercool takes on the classics at an excellent price. The denim is no different, but this original-fit pair in a subtle wash is my favorite of the lot.
These are the perfect jeans. Clean, simple, with no fussy details or silly attempts at originality. Five-pocket, white-selvedge Japanese denim — washed once so that they’re easier to break in. These will last forever and just look better and better over time.
I’m looking for a solid pair of chunky black shoes (not Doc Martens) for my 501s.
It’s cute that you think you are maybe too good for Dr. Martens. I used to be like you, but I eventually came around. While we wait, here are some options.
The French-made two-eyelet derby from Paraboot dates back to 1945 and is crafted from supple, smooth leather. It can be dressed up or down. You really can’t miss.
I love an understated shitkicker. These derbys from Nanamica are waterproof and made of a cool brushed leather. The sole is thick enough to put these firmly in the “chunky” category.
This loafer is traditional on top, but the big-dog Vibram sole gives it the chunkiness you crave.
The brogue has taken a back seat in the last few years, and I think it’s time for a comeback. I own this pair from Thom Browne, and I think they look as good with jeans as they do with a suit.
What’s a stylish mid- to heavy-weight waterproof jacket?
One can take two paths when looking for protection from the elements: tech outdoor or classic menswear. I will provide options and let you choose your own adventure. Both have merit!
When you want to take it a step further than Arc’teryx and Patagonia, you must look into Japan’s And Wander. Since 2011, the Issey Miyake alums have been making the coolest mountaineering-inspired gear. This jacket is waterproof and a bit oversize, so you can easily throw a sweater underneath for warmth.
[Editor’s Note: This jacket in charcoal gray is almost sold out at Ssense, but we found it in yellow and light gray at Renegade for $479. There are also more And Wander jackets at Mr. Porter.]
The Bedale is a classic that only gets better with time. You might not hunt, fish, ride horses, or spend any time in the Northeast, which is totally okay. The design is simple, the hardware is rugged, and the lining isn’t bulky. You can send it in to be rewaxed, and it comes back feeling brand new even after years of wear.
I trust Icelanders to make good outerwear. The Keilir Paclite jacket is made from windproof and waterproof Gore Paclite material and features a nice tonal logo. It even has a packable hood for when it really starts pissing.
I have been meaning to buy one of these for years. It doesn’t get more timeless than this. It’s handmade in Scotland, water-repellent, and has a throat latch, underarm eyelets, and hand-finished, fully taped seams. An adjustable interior tab attaches to one of the collection’s interchangeable linings for extra insulation.
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