Is it better to look fabulous or to travel lightly? This common packing dilemma hangs on the choice between fashion and function. But where there's a will, there's a way to master the art of dressing well—no matter what the weather—and packing intelligently. With the right combo of versatile, classic, and seasonally appropriate pieces, you can look chic and put together in any season. Here's our guide to packing well in spring, summer, fall, and winter.
When traveling during spring, the most important thing is to be prepared for unpredictable weather. Clothes should be multifaceted. Wear light layers such as swingy linen sweaters, featherweight cardigans, and silky camis in neutral colors. Looser-knit sweaters and cardigans layered over tees and camis will generate a sufficient mishmash of outfit possibilities. Add a classic jean jacket, which can be paired with either shorts and a tee or a simple silk dress for a more elegant appearance. The Pilcro Avie Denim Jacket from Anthropologie, with a slightly distressed look and a darker wash, is a versatile piece.
That multifaceted requisite goes for shoes and accessories, too: Loafers, slip-ons, oxfords, and ballet flats are fantastic spring shoes, especially when they can transition from day to night. These Jeffery Campbell d'Orsay flats look just as chic with shorts as they do with a more formal frock.
Spring, with its unpredictable downpours and fluctuating temperatures, calls for clothing that can effortlessly accommodate everything from a balmy, sunny afternoon to a brisk, rainy morning. In terms of accessories, a good-quality, travel-friendly umbrella is essential. And you might want to pack a raincoat, too. The Trail Model Raincoat from L.L. Bean offers plenty of coverage with its longer length, and it folds up into its own pocket for seamless packing. Waterproof shoes aren't crucial, but shoes that can withstand rain are a smart choice for trips to temperate climes where spring brings unpredictable and often rainy weather.
For comfort in the midst of weather fluctuations, think layers. Pack one light sweater and one blazer, which can be worn together or separately, depending on how cold you are. Long-sleeved cotton or synthetic-blend button-down shirts with sleeves that can be kept long or rolled to the elbow will help you deal with weather changes as well.
Sun protection is key on a summer trip. We like Warby Parker's Flannery aviators, a timeless shape that can be purchased with or without prescription lenses. Lightweight scarves provide additional shielding from the sun when wrapped around your head or shoulders, and a squishable, packable hat is even better.
Yes, linen and cotton wrinkle. But we nonetheless pack these breathable, versatile fabrics for summer travel. (If wrinkles happen, take them out with a travel-sized bottle of Downy Wrinkle Releaser or use the iron in your hotel room.) This cotton two-tone dress from ModCloth in gray and green seersucker can be worn with flats or sandals or dressed up for dinner with a blazer, heels, and a statement necklace.
During summer, it's all about T-shirts and polo shirts—especially if you're traveling to a tropical or beach destination. A tee can go from the beach to dinner when worn with a blazer or cardigan and cotton pants.
A pair of lightweight shorts shouldn't take up much room in your bag. During a particularly hot summer trip, you might want to forgo jeans. They're heavy to pack and they're warmer than, say, a nice lightweight pair of khakis on a sunny July day.
Let's talk shoes: Sandals are tricky. Sure, they keep your feet cool. But in some destinations, sandals aren't appropriate attire for dinner or other less casual events. A pair of sandals like these waterproof Newport shoes from Keen are ideal for hiking and long walks but would look a bit out of place in an upscale Italian restaurant. In lieu of sandals, perhaps try slip-on sneakers, like this pair from Coach. They're pretty versatile: They go equally as well with shorts as with khakis and a blazer.
Don't forget sunglasses and a hat to block the sun, both essential for summer travel.
One of our favorite fall tricks: Use a dress as a skirt by wearing a pull-over sweater over the dress. For example, this long-sleeved dress from Anthropologie would work well on its own on a not-so-cold fall day. But throw a cable-knit sweater over it and you've got an entirely new (and warmer) outfit.
When it comes to accessories, scarves are a very smart choice for fall travel. They can change up your look, add interest to an outfit, and add warmth on chillier days. J.Crew's classic silk-cashmere wrap has a very lovely drape, comes in several neutral colors, and can be worn with a dress on more formal occasions.
Like spring, fall demands lots of layering, as well as some thoughtful preparation for unpredictable weather. At least one sweater or sweatshirt, in addition to a nicer jacket or blazer for less casual excursions, will afford lots of options for fall outfits.
Depending on when you're traveling, you'll want to get strategic with your coat. Early fall trips with more summerlike weather might necessitate a lighter coat, like J.Crew's lightweight Broadmoor Quilted Jacket.
Simple shoes such as brogues or loafers are perfect for fall weather. Brogues work well for business or pleasure; they're comfortable, but they look perfectly presentable worn with either a suit or jeans and a button-down. Frye's Phillip Oxford is a great choice. The shoe's classic profile and slightly distressed look help its wearer transition from casual to business.
A coat, a hat, gloves, and a thick wooly scarf or two can take up a lot of suitcase space. So, when it comes to winter packing, it's doubly important to get strategic with what you choose to bring. A flannel button-down shirt or a thin cashmere crew offers the warmth of a sweater without all that bulk. It's also smart to invest in a winter coat that's suitable for traveling—one that provides a high level of warmth yet isn't unwieldy.
I'm a big fan of flat, knee-high boots for winter travel. If you can find a comfortable, high-quality leather boot, it may be the only shoe you need to bring on your travels. Make sure your boots are water-resistant if you're traveling to a snowy destination. (In many places, such as European cities, streets may not be shoveled or plowed after a snowfall.) You also want a boot that isn't too tight on the calf, as you don't want to wear anything too restrictive during air travel.
Your winter travel wardrobe should include a hat, a scarf, sunglasses (especially for snowy, high-altitude destinations), gloves or mittens, wooly socks, and, if your destination gets particularly cold in the winter, insulated undergarments like a pair of thermal pants and a thermal shirt.
Picking the right winter jacket can be daunting—you want plenty of insulation but you don't want a coat that weighs 10 lb. and takes up three-quarters of your suitcase. Look for a winter coat that features lightweight insulation, such as the Thermoball Hybrid Jacket from The North Face.
Doing the right thing
Recreate Your Home Environment
One thing that I always do when staying in a hotel is make my surroundings as home-like as possible. At home, I keep my keys and wallet on a table near my door, so I recreate that in my hotel room by placing a bowl or box near the door for my purse, keys, wallet, ChapStick, etc. That way, I never forget to grab something essential as I'm heading out for the day. I also unpack my clothing into the same dresser-drawer configuration that I use in my own dresser at home, and I arrange my cosmetics and toiletries in a similar fashion in the bathroom. I even charge my iPhone in the same location as I do at home. It sounds a bit type A, but it keeps me organized during hectic trips—and it ensures I never leave anything behind.
Use Packing Aids
Packing cubes, folders, and compression bags don't just save space; they also lend your suitcase a military-grade level of organization. Do some research before purchasing any packing aids, since some are bulky, overpriced, or both (we've reviewed a few favorites). In a pinch, grocery bags or gallon-sized zip-top plastic bags work, too.
Use Packing Lists Before and During Your Trip
You should always make a packing list before you even pull your suitcase out of the attic. (And to get started, download a copy of our Ultimate Packing List.) But what about when you're on the road? It may be a good idea to print a duplicate copy and pack it in your suitcase. When you're repacking at the end of a long vacation, you can check items off as you place them back neatly in your luggage.
Since Apple introduced its Passbook feature in 2012, I've found myself using (and losing) fewer printed boarding passes. When checking in for your flight or train reservation, select the option to download your boarding pass to your smartphone. Then at the airport, the gate attendant will simply scan the bar code or QR code that appears on your smartphone screen. (Don't have an iPhone? Similar features are available on Android, BlackBerry, and Windows Phone, and many airlines have built boarding-pass technology into their mobile apps.) This technology is especially handy when juggling multiple itineraries on a multicity trek.
Organize Your Technology
Carry a lot of technology with you on your travels? Then you know how easily cords get tangled and gadgets get lost. Cocoon makes a number of accessory organizers that feature GRID-IT!, an organization system that includes rubberized elastic bands to hold your chargers, headphones, backup storage, and other accessories in place. (Some GRID-IT! cases even come with pockets for your tablet and computer.) These flat, lightweight cases fit easily into carry-on bags and prove invaluable on the road. Never again will you spend the first day of your vacation untangling headphone cords and searching for your lost power cord.
Carry a Well-Organized Wallet
Of course, you can go as digital as you'd like, but you'll still need someplace to stash decidedly analog belongings such as cash, credit cards, identification, and so forth. A high-quality, well-organized wallet is indispensable for travel: plenty of pockets for clever storage, but not too bulky to pack and stick into your pocket or handbag. Brookstone has a number of smart options with sufficient organization for your passport and boarding passes, while Bellroy's leather travel wallet earns praise for its clever, sleek design and included mini travel pen.
Download Itinerary Apps
The days of juggling printouts of flight info, hotel reservations, rental-car confirmations, schedules, maps, and directions is over. With the help of itinerary apps, you can organize all of your itineraries on your smartphone. My favorite is TripIt: Simply forward confirmation emails to TripIt and it will generate a complete itinerary for you; then customize your itinerary by adding maps, directions, and notes. You can even share your account with others, making group travel a cinch. Many apps feature mobile airport alerts as well, so you'll know if your gate changes or your flight is canceled or delayed.
Living out of a suitcase can lead to a very disorganized vacation. When you arrive at your destination, always unpack immediately, even if your trip is a short one. Fold clothing and place it into dresser drawers, hang up any garment that may wrinkle, arrange your shoes in the closet, and unpack your toiletries in the bathroom rather than leaving them in their quart-sized plastic baggie. You'll feel more relaxed and at ease, and you won't be pulling clothing out of a rumpled pile on the floor.