How (And What) To Pack For a Weekend Getaway

All right, here's the situation. It's February, and Robin and I are gonna be spending a weekend in New York City. We're gonna take the train because it's quick, it's easy, and it's relaxing. And while we're up there, these are the things we're gonna be doing. Cocktails and a nice meal, just the two of us, walking around, maybe doing some shopping, dinner with a couple friends, a really nice restaurant, an early brunch, and then finally heading home. So let's get packing. I'm Brian Sacawa, this is He Spoke Style, advice and inspiration to help you dress well, develop your personal style, and be more confident. So in this video, I'll be showing you what I'm gonna pack for this very specific situation. I'll go through the basics, those essential things that I always have to have with me when I travel. I'll show you the specific clothing, shoes, and accessories that I'll be packing. I'll do a rundown of each individual outfit I'll be bringing. And finally, I'll show you how I actually pack it all. Now, although this is very specific to my particular situation, if you follow the framework that I laid out at the beginning of the video, it'll be very easy for you to adapt it to your specific needs when you're planning your next trip. The first thing to consider is when you are going. What season is it? What's the weather gonna be like? It's the first step in planning what to pack. Second, how long are you going for? This'll start to help you focus in on the amount that you'll need to pack, how big of a bag you're gonna need, and also some specifics like how many pairs of underwear you should bring. Third, where are you going? Different destinations require different clothes. So what I bring for a weekend in the city is gonna be very different than what I bring for a weekend ski trip. Fourth, how are you traveling? Car, bus, train, plane? That impacts not only the type of luggage you'll bring, but also the outfit you'll wear when you travel. And finally, and probably most importantly, what are you going to be doing while you're on that trip? Knowing your itinerary, where you're going, where you're eating, the dress code or vibe of each of those things is essential to planning each specific outfit for your trip. And planning ahead is what this all really boils down to. Knowing when you're going, where you're going, how long you're going for, how you're traveling, and what you're gonna be doing makes it so much easier to pack more effectively and efficiently. All right, so now let's actually talk about the basics and I'm gonna head over to the desk to talk through those things beginning with my luggage. So the bag I'm gonna take is this rolling carry-on. It's very lightweight, it's got plenty of room. The two dividers here make it really easy to secure everything inside. It's very easy to stow and both the telescoping handle and wheels make it really comfortable and easy to maneuver. For weekend trips by car, I will typically use a duffel bag, but since this trip is gonna involve train stations, taxis, and subways, the wheeled carry-on makes a lot more sense. Now, two of the biggest challenges when packing any type of bag are keeping things organized and having enough space. And one of the easiest ways I've found to solve both of those problems is by using packing cubes. I absolutely love these things. Everything is organized and contained. Things aren't getting mixed together or coming out the side of the suitcase when I'm trying to close it. For a short trip like this, I will use one of these in place of my regular Dopp kit just to save some space. But my favorite part about these is that they are compressible, which really helps you maximize the space in your suitcase. Now, when I travel, I like to read, but the problem with bringing a book is not only is it heavy, but it takes up a lot of space. That's why one of my basic travel essentials is a subscription to Audible, today's video sponsor. In addition to lightening my suitcase and giving me more space, what I love about Audible is the incredible selection of audio books, literally hundreds of thousands of titles that they have across every genre. Right now, I'm in the middle of Spare by Prince Harry, which I highly recommend checking out. It's very interesting and inspiring. As an Audible member, you're able to choose one title a month to keep from the entire catalog, and that includes the latest bestsellers and new releases. Members also get full access to a growing selection of included audio books, Audible originals, as well as thousands of podcasts, and you can download and stream all included titles as much as you want. Let Audible help you discover new ways to laugh, be inspired, or be entertained. New members can try it free for 30 days. All you gotta do is visit audible.com slash hespokestyle or text hespokestyle, all one word, to 500-500 to try Audible free for 30 days. Up next, a couple of small things. First, gotta have some headphones to listen to those audio books, podcasts, and music, and I always take a power bank or two with me to keep my phone topped up throughout the day. Nothing worse than running out of battery. Now, anytime you are stuffing clothing in a suitcase, it's gonna get wrinkled. There's no way around it, and that's why I always travel with a steamer. I never rely on my hotel to have one, and if you've ever tried to use an iron as a steamer, you know it doesn't really work that well, so that's why I always make room to pack my own. Another clothing maintenance tool that I always travel with is a clothing brush. Helps me keep everything lint and pet hair free, as well as looking clean and new. And finally, we have a watch roll. You guys know me, I like to have options for the wrist, and for the variety of things we're gonna be doing, from casual to formal, I'm definitely gonna need more than just one watch. All right, so those are the basics. Now I'm gonna quickly run down my entire packing list to include all the clothing, shoes, and accessories I'll be bringing with me. I'm only gonna bring one coat with me, so it needs to be warm, it needs to be versatile, so I'm going with a classic camel overcoat. Next, brown plaid sport coat and gray chalk stripe flannel suit for my tailored items. Because it's winter, I'm going heavy on cashmere sweaters. I've got a black turtleneck, a cream turtleneck, and a navy v-neck. Two shirts, a light blue button-up, and a denim button-down. Three pairs of pants, mid-gray flannel, blue jeans, and black jeans. Since space is at a premium, I'm going with only two pairs of shoes, formal and casual. We've got brown Oxfords and white leather sneakers. On to accessories, a tan knit hat, a big brown scarf, a brown silk patterned tie, white silk pocket square, two white t-shirts, two pairs of underwear, two pairs of gray socks, one pair of blue socks. And for watches, we're going with a watch number one on a mesh strap, watch number two on a brown leather strap, and a watch number three. So that kind of seems like a lot, but it really is the minimum that I need for the range of things that we'll be doing. And it also ensures that I'm not gonna be wearing the same outfit more than once. I'll show you how I'm gonna pack everything in just a bit. Trust me, it is going to fit. But before I do that, let me give you a rundown of each individual outfit that I'm going to be wearing. So the first look here is the outfit I'll be traveling in from Baltimore up to New York. We've got the camel coat, black turtleneck paired with some medium blue jeans, big brown scarf, tan knit cap, white sneakers, and the watch. It's casual, but a nice mix of sporty and tailored with the overcoat and the sneakers. But the most important thing is that it's comfortable, which is exactly what you want when you're traveling. Look number two is for our evening out together after we get in. You can see that I've repurposed the black turtleneck that I wore on the way up and paired it with a brown Glenclad flannel sport coat and some mid-gray flannel pants. Anchoring this look are the brown Oxfords. And on my wrist, we have a beautiful watch. Didn't wanna be too fancy, but definitely wanted to be elegant and refined. So a turtleneck with a sport coat is a great way to do that. And of course, camel overcoat pairs effortlessly with this look. So for running around the city the next day, doing a little shopping, we're going with a slight variation of the first travel look. Once again, the camel coat, which I'm pairing with a cream colored cashmere turtleneck, black jeans, white sneakers, big brown scarf, tan knit hat, and the watch. I feel like this look is very New York. It's cool, it's a little edgy. It also feels very simple and effortless to me. So really the perfect look for a morning and possibly afternoon running around the city. I am a firm believer that you really make your own occasions to wear the things that you want to wear. And fancy dinner with friends in New York City is the perfect opportunity to put on my gray double-breasted chalk stripe flannel suit. I'm wearing it with a light blue button-up shirt, which I paired with a brown silk pattern tie to tie in, seriously, no pun intended, with the dark brown Oxford shoes. Dash of elegance in the breast pocket with the silk pocket square, and as well as on the wrist. Throw on the camel overcoat and I am ready to head to the restaurant for a tasty cocktail, delicious dinner, and great company. Look number five needs to pull double duty because we're having a casual brunch before we head to the train station to travel back home. So I'm going with a navy v-neck layered over a denim button-down and paired with some medium blue jeans, white sneakers, big brown scarf, and the watch on the wrist. Nothing fancy at all, just casual and comfortable, great for an easy brunch and a two and a half hour train ride back home. All right, so you've seen my essentials, my entire packing list, what each outfit looks like. Now it's time to pack it all up. All right, so first thing I'm gonna pack up are my tailored items, beginning with my pants. Now the way I fold my pants when I pack them is to just fold them in half once and then one more time so they're folded into quarters. Next, the jackets. Now the trick to folding a sport coat or a suit jacket so it packs well is to basically turn one of the shoulders inside out, then you nest the other shoulder inside of that, make sure everything's lined up, and then fold the jacket in half. Now once again, shoulder goes inside out, other shoulder nested inside that. Everything's lined up and fold it in half. These items go into the large packing cube and I'm not gonna compress it just to keep them as wrinkle-free as possible. Shirts next, now the first thing I do is to button up most of the front of the shirt, turn it over, fold one sleeve over and then bring the cuff up to the collar. Same thing with the other sleeve. Then I will fold the shirt over into thirds and into thirds one more time and that's how I fold the shirt. So one more time here, button up the front, flip it over, fold each sleeve over and bring the cuff up to the collar into thirds lengthwise and then into thirds one more time. Next I'm doing the sweaters, nothing fancy here, just folding the sleeves under and then folding the sweater in half once more. Then in this cube, I'm also gonna put my jeans and two white T-shirts. All that goes into the cube, zip it up and compress to save some space. Socks and underwear into the small cube, zipped up and compressed. For my tie, I do have a travel case that I like to use. I'll fold the tie in half twice, put it into the case, buckle it in and zip it up. Toiletries next, as I mentioned, using another cube instead of my regular Dopp kit to save space in my bag. Now the fun part of packing everything into the carry-on. On the left side, that's where the large packing cube with my tailored items goes. I'm also going to put one shoe on the side as well as the watch roll. On the right side, first the medium packing cube up there, then I'm going to lay the tie case to the left of that. Toiletries next, followed by the second shoe. Clothing brush goes here, travel steamer goes here and the cube with the socks and underwear goes here. Cinch that down, throw the power bank in right here and the pocket square over here. Then all I got to do is close it up, zip it up and I am ready to go. And voila, there you have it. I'm packed up, I'm ready to go. I actually really need to get out of here to make it to the train. But before I do, I've got two things for you real quick. First, of course, I want to thank Audible for sponsoring this video. Reminder to go to audible.com slash HeSpokeStyle or text HeSpokeStyle, all one word to 500-500 to try Audible free for 30 days. And second, if you want some more winter outfit inspiration, got that playlist right over there for you. Click that, there are eight videos and whether you're looking for suited looks, casual looks, sweater looks, or just some ways to upgrade your winter style, that playlist will have everything you need. I'm out of here.