Packing Light and Dressing Right

travel light and stylish

The recent passing of the Summer Solstice opens the beginning of travel season; weddings and vacations are now in full swing, and everyone’s starting that pre-trip scramble to make sure they have the things they need. For me, midsummer means another burst of trade shows is about to kick off. As my numerous posts on my packing imply, I find packing for travel pretty enjoyable and I’m always looking for ways to streamline the process. There are many great guides on ultralight packing while traveling, but I find that they generally sacrifice style in the process. Sure, you can travel Europe for two weeks with only a pair of crosstrainers, a tshirt, and zip-off hiking pants, but that’s not the type of vacation that people on this blog dream about. Traveling light is great, but how can we do it without looking terrible?

I think it goes without saying, but here are some benefits of traveling light (for this article, packing light means sticking to a carryon for air travel):

  • Less time at the airport. No time at the checkin counter before, and no time at baggage claim after. Easy win.
  • Less fees. I hate luggage fees, but the great part is that you can just avoid them entirely by simply sticking to a carryon (except for those really miserable airlines that charge you for having stuff in your pockets).
  • It’s harder to lose things. Anyone that has had luggage lost (*raises hand*) knows how miserable this is. It’s pretty hard to do if you can keep all of your belongings with you.
  • You can go farther and go faster. It’s easy to move with just a wheeled carryon, so your “walking radius” increases while your transit time decreases.
  • You can access anything mid-flight. Need to take out your contacts? Grab a sweater? Take an aspirin? Everything’s right there with you.  

With those perks laid out, here’s how I’ve learned to keep it to a carryon – without sacrificing style.

1. Stick to simple, versatile clothing. This sounds like a no-brainer, but it’s worth repeating as it can be surprisingly hard to put into practice. I find that vacations are exactly when I want to wear all of my coolest clothing, but actually attempting to do so always seems to result in overpacking. Don’t bring two things if one thing can do the job, and focus on pieces that can pull double duty. If you can only wear it in one situation, do your best to avoid bringing it unless an event requires it. For me, this means that most of my suitcase is devoted to core pieces like a pair of denim, oxford and chambray shirts, a pair of chinos, a tshirt, and a bit of outerwear. As for footwear…

2. Keep it to two pairs of shoes – one on your feet, one packed. This one is really hard, but it’s the cold truth. Shoes take up a ton of space and can’t be compressed much, so they’re a big space sink. I struggle with this at times, but I try to limit myself to one pair of welted shoes (something versatile like brown chukkas or bluchers) and a pair of sneakers for most trips. There have been times that I’ve gotten away with three – one on my feet, one packed welted pair, and one packed pair of sneakers- but it’s difficult. If you only have to pack one pair of shoes, you’ll be in a good position to keep everything in a carryon. And on that note…

3. Wear your heavy shoes on the plane. I often see advice about wearing loafers for ease of passing through security, or wearing sneakers on a flight since they’ll be more comfortable. Those reasons make tons of sense, but only if you’re ok giving up a bunch of suitcase space for extra shoes. If you’re only bringing two pairs, wear your bigger pair (probably the welted pair) onto the plane. Planning on taking a pair of boots on a winter trip? Good luck fitting those in a carryon.

4. Likewise, wear large outerwear to the airport. If your packing list involves heavy outerwear like an overcoat or trench, plan on wearing that onto the plane. It’s not hard to fold and store these while on a flight, and they double as a blanket if you get stuck on one of those freakishly cold flights where the air is on full blast the whole time. Plus, the many pockets are great for storing things while running through the airport and passing through security.

5. Ditch the dopp kit. I enjoy using a dopp kit and bring one when space isn’t an issue (like on short weekend getaways and road trips), but how important are they, really? It’s just a bulky container that holds smaller containers. A small ziploc will be a lower volume way to keep all of your toiletries separate, and you won’t be as sad if something explodes. Also, don’t forget that many small items like toothpaste and shampoo may be readily available at your destination, so don’t bother bringing them if you don’t need to.

6. Don’t be afraid of washing clothes on a trip. Taking eight shirts, eight pairs of underwear and sixteen socks for a weeklong trip will pretty much consume all space – what if you could do half of that? A quarter? The secret is washing clothes so that they can be reworn – items that don’t change much day by day (like underwear and socks) are the best choice, as well as other repetitive pieces (if you’re going to wear a blue OCBD every day, why not bring less of them?). If you’re staying in hotels, it’s not that hard to clean clothing in the tub or sink and hang dry. If you want to get fancy, you can bring a sturdy plastic bag to wash in and a travel clothesline. And most hotels and city neighborhoods will have laundry services as well, so there’s no need to do it yourself if you don’t want to. No matter how it’s done, though, doing a little bit of laundry every couple of days can be the difference between a stuffed checked bag and a blissful carryon.

7. Think small and light for clothes that don’t matter much. – Since we actually want to look good on our trip, we can’t make as many stylistic sacrifices as a true ultralighter. But for items that cant be seen, why not? When I’m traveling I bring socks and undergarments that are highly compressible. My choice for high-performance and low-volume underwear is Uniqlo’s Airism boxer briefs, which are inexpensive and (in my opinion) a better alternative to popular options like ExOfficio. I also prefer Uniqlo’s new mesh Airism ones over the original because they’re more breathable. Either way, the difference in volume between these and a cotton pair of Hanes is dramatic.

8. Get creative with versatile tailored clothing. If you need to bring tailored clothing on your trip, go for something that can be split up and worn as separates. I commissioned my “blazersuit” for exactly this purpose – it can be a suit, a navy blazer, or a pair of dress trousers. As for how to pack it – sometimes I prefer to wear it onto the plane, other times I use Jesse’s method for packing a suit.

9. Plan out what you’re going to bring, and then put some back. This is also common advice, but it’s worth repeating. Overpacking is easy, so give yourself the time you need to plan everything out and then trim from there. I often catch myself packing several very similar items (like chinos in tan, off-white, and white), and having it laid out in front of me helps me see those redundancies. That’s why I started doing those packing laydowns, actually.

10. Don’t buy any gifts for anyone while abroad. You need that space for that dope new overcoat you just bought – kind gestures towards your loved ones won’t help you fit it in. Just kidding…kind of.

That’s how I do it. Or attempt to, at least. Having the right luggage is key, too; I try to keep everything in a 33L case from Muji and a briefcase from Linjer (or my Ernest Alexander bag for more casual trips). How do you keep your trips to a carryon without sacrificing style?