5 Foolproof Airport Outfits for Your Flight Home for the Holidays

If you’re heading home for the holidays, chances are good that you’re already dreading navigating the airport, getting through security, and trying to come out the other side with all of your belongings in tow and your dignity intact. Though it might not seem like the highest priority, figuring out what you’re going to wear to the airport can actually end up alleviating some of the stress that results from sharing a public space with hundreds of your closest friends. After all, if you’re dressed the right way, you’ll look good but feel comfortable, and you’ll stay cool but have options if you need to get warm.

The key to mastering airport style is to think in layers. If you’re trying to pack efficiently, you’ll often end up wearing the coat or jacket you need for your trip to the airport and onto the plane. That usually works out just fine, but don’t think that just because you’ll have your coat, all you need is a thin tee under it. Wearing the coat will probably be too hot, but wearing only a short-sleeve tee in the cabin is bound to get chilly. So it’s a good idea to wear light layers to make it more probable that you’ll be comfortable both in the airport and on your flight.

Another important consideration when you’re choosing what to wear to the airport is your footwear. You might not think that it sounds too terrible to have to unlace a pair of shoes as you approach the security checkpoint, but trust us: Everything goes much more smoothly if you come prepared with a pair of shoes you can get off and back on without much fuss.

To make things easy for you, we’ve assembled five formulae for foolproof airport outfits. The one you choose will depend on your style, the type of trip you’re taking, and what clothes you’re taking with you. But at least one is likely to work well for you to make your next trek through the airport a little bit easier, more comfortable, and more stylish.

1. Sport shirt + jacket + chinos + chelsea boots

Foolproof airport outfits no. 1

Source: Brooksbrothers.com

If your style is casual but classic, this should be your go-to airport ensemble. Start with a comfortable sport shirt, like this red plaid sport shirt from the Red Fleece line at Brooks Brothers. Add a dark pair of chinos, like this garment-dyed pair, which will be extra comfortable thanks to the modern cut of the Red Fleece line. Add in a travel-friendly jacket, like the Red Fleece three-in-one jacket, which can be worn as a parka with a down channel quilted jacket lining, as a parka on its own, or as a down channel quilted jacket on its own. And round out the look with a pair of sleek chelsea boots, made in collaboration with Edward Green, for a pair of shoes that will enable you to get through the TSA checkpoint without hassle, or easily make a brisk walk across the terminal in case of a last-minute gate change.

2. Henley + shawl-collar cardigan + trousers + driving shoe

Foolproof airport outfits no. 2

Source: Ralphlauren.com

If you’re packing your heavy winter jacket, or are flying somewhere that you won’t need it, you can wear a cardigan instead of a coat on the plane. That means that your warmest layer will be more comfortable to wear in your seat, and easier to stash in the overhead bin if you’re warm enough without it in the cabin. Start with a comfortable long-sleeve tee, like a classic henley from Ralph Lauren. Add your favorite cardigan, or a budget-friendly style like this one from Ralph Lauren’s Denim & Supply line. Then, choose a vintage-inspired pair of trousers to continue the classic look, like these trim herringbone pants. Complete the look with a classic but simple pair of shoes, like a leather driver in black or tan, and you’ll have a cozy outfit that looks timeless and won’t get in your way.

3. Oxford + vest + jeans + loafer

Foolproof airport outfits no. 3

Source: Mrporter.com

If you’re carrying a heavy wool coat with you, it takes a little bit of ingenuity to figure out an outfit that will enable you to stash your coat in the overhead bin, but not get too cold without it when the cabin gets drafty. That’s where a vest comes in handy. Choose a trim style with lots of layering potential for layering later in the trip, like Barena’s splurge-worthy shawl-collar gillet. For the flight, pair it with a simple button-front shirt, like Club Monaco’s trim flannel shirt. Add a pair of rigid selvedge jeans, like A.P.C.’s slim-fit Petit Standard. Add a slip-on but weather-proof shoe, like Quoddy’s boat shoe made of Horween Chromexcel for a comfortable and hassle-free shoe for the airport and for each day of your vacation.

4. Tee + chambray shirt + jeans + canvas sneakers

Foolproof airport outfits no. 4

Source: Nordstrom.com

If your head is really in weekend mode, you might as well run with it and go with a super-casual ensemble, particularly if you’ve already stuffed your coat into your suitcase and aren’t worried about getting too cold on the plane. Start with a trim tee shirt, like a heather gray v-neck from The Rail. Top it with your favorite chambray shirt, or pick up a new one like this workwear-inspired style from Wallin & Bros. To further the weekend vibe, wear it with a comfortable pair of jeans, like this Naked & Famous style that incorporates just a little bit of stretch for a more comfortable flight. Add a classic pair of canvas sneakers, like a navy blue pair of Jack Purcells.

5. Shirt + suit + double monks

Foolproof airport outfits no. 5

Source: Bloomingdales.com

On the other hand, if you’ll be all dressed up at your destination and are trying to figure out how to transport your suit without it wrinkling irreparably in your bag, consider wearing it on the plane (particularly if your flight is only an hour or two long). Start with your most comfortable suit (bonus points for a grey style, like Theory’s donegal silk and wool suit), and add a white dress shirt, like Brooks Brothers’s pinpoint shirt. Finish the look with a pair of double monks, like Paraboot’s sleek cognac version, which you can get off and on more easily than a traditional lace-up dress shoe.

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