Before you even begin packing, you will need a bag suited for the trip ahead. While we have already spoken at length about our favorite travel bags, for winter vacations (which skew on the shorter side), a specific category is paramount: carry-ons. The mobility and flexibility a great carry on provides is unmatched, plus for those flying avoiding checked bag fees and the carousel is a no-brainer. For those looking for the most utilitarian option, a classic leather duffel can’t be beat. From brands like Filson, Gucci or Louis Vuitton, these large bags are packable, durable, and designed for a beating. If you happy to be headed on a longer excursion, a hard case rollaway from Tumi or Rimowa is a timeless classic, with seperate compartments and interior storage aplenty. No matter which you pick, be sure there is enough space for a large dopp kit or medicine bag—arguably the most important travel accessory there is. With the right set up, fitting in all the essentials is a breeze.

Now that you have your bag in order, it’s time to fill it right? Well, technically, yes, but as we see it, your second priority—apart from not forgetting your wallet, socks, and underwear—is a cozy travel fit. Traveling is undeniably painful, so do yourself a favor and wear something comfortable. While we’re by no means suggesting you rock pajamas to the airport, a heavyweight french terry hoodie and sweatshirt (or a matching set if you’re so inclined) make that long flight or car ride all the more bearable. Not only are they good for the journey, the sweatpants double as hotel lounge wear while the hoodie will no doubt be utilized elsewhere in your rotation. Pragmatic and space-efficient, great sweats are a travel must.

Now, finally, we get to packing. Clearly, destination dictates wardrobe, however regardless of where you end up, a few items are a must. As we’ve already mentioned, socks, underwear and toiletries are a given. In terms of actual wardrobe, though, essentially every vacation requires the following: activewear, loungewear and evening wear (but more on that below). If you have followed along so far, you’ll already have the lounge portion mostly covered, though an extra sweatshirt never hurt anybody. As for activewear, unless your vacation is predominantly poolside—in which case all you need is a pair of trunks by the likes of Thom Browne or Stone Island—search for options that work just as well for exploring as they do for casual stunting.

For warmer climates, twill chinos and lightweight cargos from Japanese stalwart Engineered Garments are perfect. Pair them with a whole grip of camp collar shirts by Stussy, Supreme or Prada and you’re pretty much set.

For those headed to headed skiing, clearly you will require something more substantial. While labels like Moncler and The North Face are practically engineered to be worn on or around a mountain, those trying to optimize for "packability" should always keep a packable down jacket on hand. Patagonia and Uniqlo are master of this particular category.

Since luggage space is always a factor, consider packable outerwear options from Arc’teryx or Acronym. Even if you’re not hitting the slopes, you’ll still fit right in.

Footwear is particularly difficult, considering space is limited and—unlike the rest of your wardrobe—shoes don’t fold. While we all wish would could bring along every pair of sneakers in the rotation, in order to avoid the dreaded check-in bag, you will need to show some restraint. For a week-long trip, three pairs should suffice.

In order to narrow things down, versatility is key. First, opt for shoes you can wear on a hike, back the the hotel and out to dinner after. Consider brands like Roa, Salomon and R.M. Williams, whose ethos revolves around day-to-night wear.

Next, an easy pair to wear on the plane—Vans slip-ons or your favorite pair of Jordans for instance. Luxury sneakers, now closer to modern sportswear than ever, are always a strong choice when looking for function and... well, flex.

Lastly, a respectable pair of shoes in the event you have an event or plan on going out—Gucci loafers are our preferred choice.

If you are mountain-bound, a fourth pair of boots may be necessary. While we already have a whole guide on the perfect winter boot, if you’re in a pinch Timberlands never fail you. The best part of all these options? Each pairs exceedingly well with the other items above, and if you pack smart, just a few pieces allow for endless possibilities.

While this doesn’t apply to everyone—particularly those of you headed somewhere remote or tropical— many of us plan on going out at least once during the course of our trip. Whether it's a formal restaurant or just a higher-end bar, there may be a more strict dress code, especially if you are headed abroad. Naturally, a full-suit is not only unnecessary, but wildly impractical given packing limitations. Instead, if you cleverly re-work your day time wardrobe, with just two items day-time casual transforms to nighttime chic.

Consider packing an unstructured blazer and trousers alongside the rest of your clothes. Pair the two with a camp collar and the loafers you should have already packed, and you have a near-perfect vacation fit.

Are patterns too wild for you and don't dig the Miami Vice-vibe? Swap the button-up for a slim-fit T-shirt or (in the case of the mountains) thin turtleneck for a more minimal look. Regardless, with just two easily packable pieces, your predominantly relaxed vacation clothes can tackle just about anything.