How to Pack for a 3-Day Trip (4 Different Scenarios)

This. was not easy packing for a trip sounds pretty straightforward until you start thinking about everything you actually need to bring a weekend getaway business trip a few days somewhere warm or a winter escape four different trips each one just three days long but each presenting a completely different challenge for one it's about having the right clothes for different occasions for another it's figuring out how to pack a suit and when you're dealing with bulky winter clothing there's the question of whether everything is even going to fit so in this So in this video, I'm going to walk you through Exactly how I'd approach each trip, what I'd bring, how I'd put the outfits together, and finally, how I'd get everything packed into one carry-on suitcase. This video is sponsored by Carl Friedrich. Now, before we get into the four trips, I want to get in front of something because I'm not just packing clothes here. There are two categories of essentials I'm bringing on every trip, and since they take up space, I know someone's gonna ask, well, what about this? What about that? So hopefully this takes care of those questions, assuming I haven't forgotten anything. First up, tech stuff. Laptop, laptop charger and cable, Kindle, phone charger and cable, Oura Ring case, AirPods, and the AirFly 2 just in case. And then we have our miscellaneous essentials. Dopp Kit, glasses case, catch-all, watch case, because I gotta have two, pen, travel shoehorn, a few pairs of underwear, and a few pairs of socks. Color subject to change. Now, all of the tech essentials and a couple of the miscellaneous items will go into this integrated front pocket, which is one of my absolute favorite features of this suitcase It means I don't need to carry an extra small bag and everything is still easily accessible. The remaining items will go in the suitcase and that's going to be part of the challenge. All right, first up is going to be our weekend getaway. And let's say we're heading to a nice hotel in the countryside for a couple of nights. We're leaving Friday afternoon, getting checked in, maybe doing a little exploring, and then heading out for a casual dinner that evening. Saturday, we're spending the day walking around town, checking out some shops, grabbing lunch. But we've got reservations at a really Really nice restaurant that night. And Sunday, it's just breakfast, checking out, and heading home. So overall, pretty relaxed weekend, but with a few different occasions to dress for. I wanna be comfortable while traveling and walking around, but I also want to look appropriate for dinner without packing a completely separate outfit for every activity. So here's what I'm bringing. For the casual outfits, I'm building everything around one pair of medium blue 501s, my Coyo sneakers, and this L.L. Bean fleece vest. The jeans and sneakers are going to work for pretty much Everything we're doing during the day and the vest gives me an extra layer without having to pack another jacket. Then I've got a few different shirts to change the look depending on what we're doing. The green sweatshirt for traveling on Friday, a vintage tartan shirt for dinner that night, a brown rugby shirt for exploring town on Saturday, and a gray chamois shirt over a cream t-shirt for the trip home. Now, Saturday dinner is where I'm making a completely different choice. I'm bringing this gray Prince of Wales sport coat, white dress shirt, charcoal flannel trousers, a burgundy cashmere tie, And I'm finishing that off with a pair of cordovan tassel loafers. Could I dress up the jeans and make them work for dinner? Maybe, but for the kind of restaurant I'm imagining, I'd rather have a proper tailored outfit. So in terms of how this all comes together, for Friday, we have our travel outfit and then transitioning into our casual dinner look. Saturday, this is the daytime look for exploring town and a casual lunch, and then changing into something much smarter for the upscale dinner. And finally, Sunday, another simple and casual travel outfit. All right, next up, a business trip, and this one's gonna be a little more challenging because we're bringing a suit. I'll be traveling on Friday, getting checked into the hotel, and then there is a networking event and dinner that evening. Saturday is an important presentation, so a suit and tie are definitely in order, and then another dinner and some socializing that night. And finally, Sunday, Just traveling home. One thing to note is that I do not want to pack a separate outfit for Friday night, so whatever I wear for the travel portion also needs to be appropriate for the networking event that same night. So here's what I'm bringing. For Friday, I'm starting with this brown and gray houndstooth sport coat, a medium blue oxford cloth shirt, navy cotton trousers, and my cordovan tassel loafers. It's comfortable enough for traveling, but I can go straight from checking into the hotel to the evening event without having to change. For Saturday's presentation, I'm bringing my navy Amadeus suit, Thin striped dress shirt, a yellow tie from Eden Ravenscroft, a white pocket square, and black Oxfords. Then for Saturday evening, I'm changing into this flannel sport coat, a medium gray cotton pique shirt, and charcoal flannel trousers. I'll wear the cordovan loafers again also. And for Sunday, it's back to the houndstooth jacket and navy trousers, but I'll swap the blue Oxford for the striped shirt I wore with the suit. And here's how everything comes together. Here is our Friday travel look, which is designed to transition seamlessly into the evening networking and dinner. It's Saturday, getting suited up for the important business presentation before changing into something a little more relaxed for dinner and networking that night. And Sunday, I'm basically repurposing the Friday travel look but changing up the shirt so it looks a little different. Now throughout this video I've been using the Carl Friedrich Carry-On X in the dark olive and chocolate colorway part of their hybrid collection. I've tried a lot of luggage over the years and surprise surprise I'm quite picky especially when it comes to design and this is very thoughtfully designed. It's got a robust polycarbonate shell and a hard-wearing aluminum frame and instead of a traditional zipper you've got two TSA approved locks. Feels substantial, secure and there's something very satisfying about clicking it shut. And you've already seen the integrated front pocket, which keeps my laptop and other essentials accessible without opening the suitcase or carrying an extra briefcase. The smooth spinner wheels and interior compression system are also really practical, especially when you're trying to fit everything into one carry-on. And Carl Friedrich backs its luggage with a lifetime guarantee. So if you'd like to check out the Carry-On X, I'll put a link in the description as well as in the pinned comment below. All right. Moving on now to our third trip and we are going to be heading somewhere warm. And you know what? After the business trip, I'm looking forward to packing something a little more relaxed. Let's take a look at the itinerary. Friday, travel day, getting checked in and settling into the hotel. Then heading out for a casual dinner that evening. Saturday morning, going to be spending some time by the pool or at the beach and maybe exploring town and grabbing lunch. Before, a reservation somewhere nice for dinner that night. Then Sunday, breakfast and heading home. Here is the packing list. Now, since this is a casual trip, I'm keeping the travel outfit casual too. I've got this blue Lululemon set, a lightweight t-shirt, and my Koyo sneakers. And I will wear the exact same thing on the way home. For Friday dinner, I'm bringing this red and white patterned shirt, which I'll pair with some khaki shorts, same sneakers. For the pool or beach, I've got my Orlebar Brown swim trunks and this black cotton textured button-up from Quince. Then for exploring town, I'm going with a blue and white houndstooth shirt from Paul Frederick, tank top from Todd Snyder, navy shorts, and again, the Coyos. And finally, for Saturday dinner, I'm bringing this Merlot colored bamboo sport coat, a black cotton pique shirt, ivory twill trousers, and my black ostrich Belgian loafers. the outfits look like. For the Friday travel look, I'm keeping it very casual and relaxed before changing into something a little more respectable for casual dinner at the resort. Starting out Saturday morning with a pool slash beach ensemble, then this is what I'll be wearing for some afternoon exploring and lunch before changing into a look that's more appropriate for dinner at a nice restaurant later that night. And like I said before, same outfit as Friday for Sunday travel. All right, our final travel scenario is going to be a cold weather getaway, and this is the one I'm most concerned about because cold weather clothes take up a lot of space. We've got sweaters, heavier shirts, boots, an overcoat, and we're still working with the very same carry-on. But let's check out the itinerary. Friday, traveling, getting checked in and settling into the hotel, then a casual dinner at the lodge that evening. Saturday morning, getting outside, walking around, exploring a bit before heading out for an upscale dinner that night. And finally Sunday, breakfast, travel home. Here's the packing list. For the travel outfit, I'm wearing my HSS officer's coat over this waffle knit sweater from Quince and a gray t-shirt, light wash 501s, a cashmere hat, and a pair of oxblood boots. And wearing the coat and boots while traveling means I don't have to find room for them in the suitcase. For Friday dinner, I'm bringing this burgundy Ralph Lauren quarter zip over a cream brushed I'm going with a cream cashmere turtleneck under this gray L.L. Bean chamois shirt, the officer's coat again, light wash jeans, a knit hat from Drake's, and the Bostonian boots. Now, for Saturday dinner, I'm going to do something a little different. I've worn sport coats to nice ski resort hotels before, and I found that they can actually feel a little too dressed up for the setting. So instead, I'm bringing this black Ralph Lauren Fair Isle sweater, a white dress shirt, chartreuse boots, Charcoal flannel trousers and black cordovan penny loafers. I think the sweater and loafers feel a little more relaxed, but the black and gray color palette still gives the outfit that refined look that I want for dinner. Let's see how it all looks. Here we have our Friday travel look. Trying to wear the bulkiest stuff now so I don't have to pack it. And then changing into a nice business casual outfit for our casual lodge dinner. Saturday morning is all about exploring and here's what that one's looking like. Before heading back to the hotel and changing for the evening's upscale And then Sunday, well, same as Friday. So I think the biggest takeaway here is that packing well really starts with thinking through what you're actually going to be doing on your trip. Like I said at the very beginning of this video, this was not Easy. Planning things out takes time, but hopefully seeing how I approach putting together and packing a wardrobe for each of these trips gives you some inspiration and a few ideas for your next one. Big thank you to Carl Friedrich for sponsoring this video. Reminder, link to the Carry On X down below in the description and the pinned comment. And finally, thanks as always for watching and stay tailored.