A gentleman friend is planning a trip to New York City this holiday season, and has asked for our advice on what to pack. His agenda includes lots of walking around the city, an Alvin Ailey performance, a casual holiday party at a friend’s house and a few meals at cozy restaurants around town. His style specs? Earth tones and a “gentle” streetwear vibe – in other words, an effortless balance of smart and sharp. We asked around and checked out some of our favorite menswear websites, and here’s what we found. Ten pieces that form the ideal capsule wardrobe for a December trip to a big city – and it will all fit in a carry-on bag. You’re welcome!
what’s the right packing list for a gentleman’s trip to nyc this winter?
The first thing we do when packing for any trip is check the weather. Is it going to be hot or cold? Wet or dry? This is essential information, and unfortunately you won’t have a precise read on it until a few days before you go. For those who like to prepare and pack early, make some informed assumptions. And opt for layers and waterproof options if that makes sense based on your destination.
The second big decision is color palette. For a trip like this, everything needs to go with everything else. So choose a couple of dominant colors and one “pop” color, and you’ll find it really easy to get dressed in the morning. Our friend has asked for earth tones, so we’re going with a color palette inspired by a winter forest: ivory; chocolate brown; dark green; and charcoal grey. A little bit classic and little bit fresh. Bonus point: the green nods at the winter holiday season, but doesn’t scream “Santa Claus is coming to town.” ‘Cause that would just be wrong.
OK, let’s do this. Here are the 10 essential ingredients to a successful winter weekend in the Big Apple (or really any big city that may be calling your name).
footwear first
Once we have the weather forecast, our cardinal rule of packing is: footwear first. Once you have the shoes figured out, the rest falls into line rather easily.
1. leather (or suede) sneakers.
For our friend’s jaunt to the city at Christmastime, we suggest two pairs of shoes (one of which should be worn on the plane). The first is a soft-soled, somewhat refined sneaker in a neutral color that is totally comfortable and just a little bit chic. These are everywhere right now, and our only request is to avoid visible logos and brands that are just too prevalent right now (looking at you, On Running). Something minimalist and timeless is what we’re after. Like this brown leather pair from Ralph Lauren, for example. For the best effect, think white soles and medium to dark brown leather or suede uppers. Your call on whether or not they should be vegan leather.
BUY NOW: $148.
2. hard-soled shoes (or boots).
The second pair of shoes will need to take our dear friend out and about in the evening, where the dress code is a bit more formal. To keep it simple, we’d stay in the medium to dark brown family, and bring a pair of oxfords, or Chelsea boots. Either would be fine. If the sky’s the limit, this pair of Chelsea boots from British label John Lobb would fit the bill perfectly. For the rest of us, a more practical pick would be something like these classic oxfords from Allen Edmonds.
BUY NOW: $174.
second, slacks
3. casual twill trousers
Assume you’ll need 3-4 pairs of pants for a multi-day trip to NYC – one to wear on the plane, and the rest to pack. We’d definitely have two pairs of comfy cotton or cotton-blend slacks at hand. One of our friends says that her husband lives in Vuori, including when dressing for work or a night out. The brand’s Meta pant comes in a yummy color called “dark oregano” that would work perfectly with our target color palette. This cotton and linen blend pair in sage green, made exclusively for Mr. Porter, would also get the job done. Maybe one pair in some shade of green and a second pair in khaki or ivory?
BUY NOW: $210.
4. wool dress pants
For evenings out, which are colder and also more formal, one pair of “grown up” wool suit trousers seems good to have on this packing list. You can just break up a suit you already love for work, and style it differently for this trip. Or consider buying a new pair, something along the lines of the Bonobos “Jetsetter” pant, which we like in grey or charcoal for our target color palette. If you favor pleats and a looser fit, the brand also offers this option in a luscious dark brown.
BUY NOW: $225.
third, sweaters and shirts
In almost any climate, the secret to comfort is layers. ‘Cause air conditioning. Sudden changes in the weather. You know what we mean. Here are some easy ways to pack so that you’re ready, whatever the weather.
6. a work shirt.
This forest-green work shirt (which can also be called a chore jacket or a “shacket” – half-shirt, half-jacket) would be a cool piece to layer over a slim-fitting lightweight cashmere sweater. Or a striped rugby shirt. The four pockets keep it from looking too precious.
BUY NOW: $390.
7. a button-down oxford shirt.
Wear it to work with a suit and tie, or just a blazer. Lose the tie and wear it under a cardigan. Roll up the sleeves and style it with twill pants or jeans and sneakers. That’s what makes this shirt an essential classic (especially when you’re traveling and packing light). Here’s just one of the many available at Brooks Brothers.
BUY NOW: $69.
8. a cashmere sweater (or two).
Lightweight is good for layering. Chunky is a perfect statement when you’re sallying forth without a coat. Your call. If it were us, we’d bring one of each. For lightweight, we love the color and construction of this fresh white sweater from Mr. Porter. You can find similar looks at every price point.
BUY NOW: $500.
There are also lots of options for a chunkier version of a cashmere or merino wool sweater. And sure, you could opt for a print. However, if you want to purchase something for which you’ll never experience buyer’s remorse, a solid color and a distinctive “touch me” texture is always the best bet. Our male friends on the West Coast still think that Huckberry is their little secret, but it’s out there – and this delicious cable knit merino sweater is an example of why word is spreading so quickly.
BUY NOW: $195.
and finally, jackets, blazers and outerwear
For dress-up occasions, you’re going to need a suit jacket or a blazer. Maybe even a tie! Here’s some food for thought on what would work with the rest of this capsule collection.
9. a wear-anywhere blazer.
Sure, it’s an investment piece. But it’s gorgeous! This single-breasted herringbone cashmere and tweed blazer from Swiss brand Loro Piana can top a button-down shirt or a cashmere sweater with equal aplomb.
BUY NOW: $5,950.
We’ve learned that for alpha males, outwear is a fraught topic. Many forgo any kind of coat, even in subzero temperatures, because they “don’t need a coat.” Unlike the rest of us weaklings, they are impervious to the chill. If you’re one of them, skip this section. If you’d like the fashion punch and protective function of a great coat, though, read on.
10. a perfectly-fitting overcoat.
Our once and future President has been criticized for wearing a black overcoat that is way too large for him, which signals weakness, rather than the strength he is presumably trying to convey. Don’t fall down that rabbit hole! A classic single-breasted topcoat in charcoal gray (not black) like this one from Cardinal of Canada, proportioned properly for your height and weight will make you stand out in the crowd in all the right ways. And keep you warm.
BUY NOW: $1,195.
our thoughts on the right packing list for a gentleman’s trip to nyc this winter
That’s the advice we’re sharing with our friend, and perhaps it’ll help you pack this winter, too! Have fun out there, gents.
