Chris Black has returned to the Strategist with a monthly column to answer all of your burning questions, from super-specific style predicaments to workout and tennis recs to foolproof host-gift ideas that will get you invited back to the beach house.
What’s a good basic to get my boyfriend for Christmas?
Basics (or wardrobe staples, if we are being nice) are my sweet spot. There are pieces of clothing that men everywhere should own, and I don’t mean Vuori joggers or Alo mesh hats. These foundational pieces of clothing will last a long time and never really go out of style. They’re the perfect Christmas gift category, especially if your man is looking dusty.
An oxford cloth button-down belongs in every guy’s closet. It’s a hard-wearing staple that works at the office or running errands on a Sunday. Drake’s makes my favorite. The collar roll is perfect, and it only gets better with age. When the collar starts fraying, it really gets good.
A pair of black jeans is an underrated staple. Finding the right vintage Levi’s 501 or 505 for a gift would be tough. Luckily, orSlow has you covered. This pair is made from 13.5 ounces Japanese denim and has the perfect cut and wash.
A navy cashmere sweater is about as classic as it gets. I am wearing one right now. This one from Scotland’s Barrie (owned by Chanel) is not cheap, but it is very well made, so the collar and cuffs stay as God intended, no matter how often you stuff it in your carry-on or use it as a scarf.
This is the best (and most stylish) jacket for enduring the elements. It made from water-repellent bonded cotton and hits right above the knee. It will never go out of style and if you need more warmth you can just add a liner.
If I had to wear one sneaker for the rest of my life, it would be this one. A long-standing classic, they work on almost anyone. The tonal grey colorway is the original and cannot be improved on. The fact that they are incredibly comfortable is just a bonus.
Every guy needs a go-to white t-shirt. A lot of the popular higher-end versions are too thin for my tastes. Lady White & Co. is just a little boxy with a strong set-in collar. Made from a midweight cotton, it’s substantial enough and breaks in nicely.
What beanies are we rocking this winter? I can’t do another year of above-the-ear fisherman cosplay.
Beanies (or toques for our Canadian readers) are practical, but many fellas fail to wear them properly. The idea is to keep your ears and head warm. Wearing it above the ears is foolish, making it another corny accessory. I can admit that I have done it before, but it’s been a decade. Don’t get me started on guys who wear beanies in the gym or anyone still rocking the Frank Ocean-approved Arc’teryx version. Let’s do better.
This is as straightforward and high-quality as you can get. Simple and based on the original military-style watch cap, it will keep your head warm (a mix of wool and cashmere) without expressing anything, which is sometimes the best choice.
Aries is one of my favorite London brands. Honestly, I cannot pull most of it off, but I love to admire it from afar. This beanie is an exception. It’s pretty straightforward, and the logo is tonal and embroidered. The “space dye” gives a more low-key Missoni. The price is right, too.
I love cable knit. It feels deeply winter-y to me. The sweaters can often be a little chunky (unless you go cashmere), but this made-in-Scotland cable knit beanie from knitwear experts Howlin’ will keep you warm and put you in the holiday spirit.
I couldn’t recommend beanies without including a little streetwear since the counterculture, along with skateboarding, perfected the art of the logo beanie. I love this rolled-edge version from Stussy that features the logo in a tasteful chain stitch, an application you rarely see on winter headwear.
What are some good alternatives to a classic penny loafer?
Nothing can replace the classic penny loafer. It is arguably the most diverse shoe in any rotation, but I understand the urge to branch out. Below, I have compiled some viable options for when you want to give your pennies a break.
The boat shoe has had a big year, and Saman Amel’s take is the sexiest low-key version. You can wear it with almost anything, and it comes in several flavors (black deerskin, black suede, brown suede, etc.) … It’s a bit of an investment, but it will never go out of style.
[Editor’s note: Saman Amel lists its prices in euros; the USD price shown is an approximation.]
Some may find the Belgian loafer too dainty, but I have always loved how it looks with jeans, shorts, and a suit or tuxedo. This pair from Stockholm’s Morjas doesn’t have the little bow, which probably makes them more wearable for most people. You can even choose between a leather or rubber sole.
I have been campaigning for the driving shoe to make a comeback for a few years. It easily slides on and off, just like a penny loafer. It can lean a little Eurotrash, but that is on you and how you wear it. The suede will age nicely and the “rubber pebble” sole is very comfortable.
The real OG moccasin from Quoddy, handmade in Maine, should be in any closet. The pebble leather molds to your foot, and it slips on and off very easily. This timeless classic can be kept in the mudroom and worn with almost anything.
The Strategist is designed to surface useful, expert recommendations for things to buy across the vast e-commerce landscape. Every product is independently selected by our team of editors, whom you can read about here. We update links when possible, but note that deals can expire and all prices are subject to change.
