please advise

Ask Chris Black: What Are Some Nice, Warm Winter Boots for the Brutal Season Ahead?

Photo: Eric Chakeen

If you’re looking for the most powerful hair dryer or 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? Regular readers of the Strategist will know that we’ve previously turned to resident Cool Guy Chris Black (he’s a partner at brand consultancy Public Announcement) to help us answer both of those questions. For more of Chris’s advice, he’s now answering reader questions for us in 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

You’ve shown us rain boots and fall boots, but I don’t currently own a pair of solid winter boots. Any recommendations for nice and somewhat warm boots for the brutal season ahead?

Thank you for reminding me that pure hell, a.k.a. winter in New York City, is quickly approaching. Nothing I look forward to more than trudging through dirty snow on a cold, dark morning. Being prepared is critical; wet socks will make any day worse.

I swear by my Vasque Sundowner GTX boots. Simple, classic design, fully waterproof (GORE-TEX, baby!), and durable. For the price, you really can’t beat them. Pair the boots with baggy Levi’s 501s and a North Face Nuptse for the full “REAL HIP HOP” look.

Another pair I have been considering is the Hoka One One Sky Kaha. They are fully waterproof, have a Vibram sole, and are much lighter than any other option. The black-on-black style is perfect for the city.

If you must have something more upmarket, Prada makes its version of a classic Blundstone. Textured leather, commando rubber sole, and neoprene inserts. Your dogs won’t be barking in these bad boys!

The Strategist recently helped a female reader find a “short, cool” puffer for $180 or less. Can you point me to some men’s puffers that meet the same criteria? 

I didn’t embrace the puffer until a few years ago. I always felt a bit silly in them, and thought I looked like the Stay Puft Marshmallow Man (maybe I do?). Then I quickly realized that the puffer is the most practical style of winter jacket on the market. I haven’t looked back since.

My No. 1 will always be from the gods at Patagonia. The Micro Puff Jacket may be a little more than you want to spend (though both REI and Backcountry are now selling a handful of new coats in past seasons’ colors at a discount), but it will last forever, and if anything goes wrong, the brand offers to fix or replace stuff bought from it or authorized retailers. A true investment. Also, so many fun colors! I love the Peppergrass Green above, but black is probably a more practical choice.

The Ultra Light Down Puffer from Uniqlo is thick, puffy, and water-repellant, and comes in at the right price. I love the orange! Think of it as a mood lifter for those dark winter days.

Montbell also makes a well-priced ($179, perfect!) and cool-looking down jacket. Very light, incredibly warm, easily packable — it comes highly recommended by people I know who actually enjoy doing shit outdoors. Since walking to Whole Foods in January is my version of hiking … I trust them.

I’m starting to think about holiday gift shopping, and one thing you read about everywhere as a great gift is candles. But they’re so prevalent that I’ve developed a bit of candle fatigue. What are some other relatively inexpensive but substantial-feeling things to give that might strike the same note as a candle, but aren’t a candle?

Candle fatigue! It could never happen to me. But I see your angle. A candle, while a wonderful gift, will eventually cease to burn. The opposite of the gift that keeps on giving. Something in a similar price range, with a little more lasting power, should do the trick. May I?

A chic hand soap still gives the gift of scent but lasts a little longer than 60 hours. I keep a bottle of Byredo’s Vetyver hand wash from in my water closet, and it receives rave reviews.

I also like Grown Alchemist’s sweet orange, cedarwood, and sage hand soap. It smells great and is infused with coconut oil, making it super hydrating — something we all need during the colder months.

What about something useful (and beautiful) for the kitchen? A classic French press is a kitchen staple, and Yield Design Co.’s handmade glass version in an alluring shade of amber would look good in use or just sitting out on the counter.

If that doesn’t work, go with a classic from Le Creuset. I am partial to the white, but as with anything Le Creuset, there are many more colors to choose from. The options are practically endless!

A well-designed corkscrew is something any home should have. Italian designer Alessandro Mendini created a cult classic for Alessi in 1994 with the Anna G. Corkscrew. It also comes in a myriad of colors.

Another good option is the sky corkscrew from Georg Jensen in a sleek polished stainless steel. I don’t even drink, and I want to buy one!

The Strategist is 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 best acne treatments, rolling luggage, pillows for side sleepers, natural anxiety remedies, and bath towels. We update links when possible, but note that deals can expire and all prices are subject to change.

Ask Chris Black: What Are Some Nice, Warm Winter Boots?