Growing up in a hospitality-driven family (my mother works for Alaska Airlines and my father in hotels), getting upgraded was always a coveted possibility. With an employee's handbook in hand, my mom used to chide me on sloppiness before boarding a flight. No sweatpants. (Not even the Juicy Couture kind.) Check. Polished heels with flats to change into. Double check. Granted, some of it was old school, and especially in our casual dressing times, perhaps not necessary, but a lot of it has stuck with me. The truth is, looking good actually helps when angling for an upgrade. Here are a few style picks with the luxuries of first class in mind.
Look 1: First Lady Chic
Nothing stands out in the airport terminal like a cool and collected look. With election season in full swing, first ladies are a good guideline. Their styles tend to be more structured and in favor of texture, like this boxy boucle tweed coat ($280 by Rory Beca) with metallic threads that will (hopefully) catch the eye of the gate agent. For a take on the modern skirt suit, pair with a bateau neck sweater in the same color family ($17.99 at Target) and bright tweed pencil skirt in head-turning cobalt ($75). Though, flats are comfy, stow them in this handsome designer bag by Reed Krakoff ($1,090). This is the time to pay attention to your footwear. A classic pump, especially in this leg-lengthening nude patent ($59 by Nine West), with a moderate heel will go a long way at check-in. (So will batting eyelashes, but you didn't hear that from us.)
Look 2: Movie Star
It used to be first class was a denim-free zone. Those days are long over, so take cues from A-listers who lay all the way back in first class wearing dressy jeans. We like style arbiter Gwyneth Paltrow's style: the mom of two flits between London, New York, and LA looking just about perfect. Paltrow often wears skinny jeans—here, we selected a pair by another famous frequent flier, Victoria Beckham ($265)—tucked into boots like these by Burberry in walnut brown ($850). On top, she sticks with a classic button-down, maybe in a light blue ($117 by MIH Jeans). In case of chilly cabins, bring along a shearling jacket, cut into a hip motorcycle shape ($2,115 by Acne). Budget watchers can try faux versions, or go to Asos.com for more affordable price points. Accent with a simple stone drop necklace ($96)—agates are all the range—and pull all your documents together with a hot pink travel wallet ($145.99). Just remember to take off your Jackie O sunglasses while chatting up the check-in agent.
Look 1: Dandy CEO
Play the part of a mover and shaker. Sure, a regular suit will accomplish the head honcho look, but stylish business casual makes a stronger, cooler impression. British menswear is a good guiding light. Look in your closet for gray trousers, or French Connection makes nice flat-front designs ($198). On top, throw on a striped blue shirt, maybe with a tweak like this Rag & Bone design with partial button-down placket ($205). To highlight English dandy style, slip on wing-tip oxfords ($188 by Allerton) and loop on a menswear print scarf, like this one in houndstooth by Ermenegildo Zegna ($185). But, if there is one category to invest in, it would be outerwear. A traditional trench coat by the Mackintosh or Burberry ($1,295) will last you ages and add tremendously to your wardrobe. Lastly, these Bose in-the-ear headphones ($129.95 for music and calls) will comfortably stay in place hours into your flight.
Look 2: Jet-Setter
These days, first class regulars don't always have your usual desk jobs with humdrum dress codes. So, take inspiration from bad-boy-look-aficionado/millionaire Brad Pitt. Pitt's jet-set look is polished but also kind of rebellious. There's a hint of that in these black motorcycle boots ($219.99) and Ray-Ban folding aviators that neatly tuck into breast pockets ($244.95). On top, the actor usually goes for something basic with an athletic feel, like a three-button henley—we like this one in rich Bordeaux ($18.36). Just add your favorite denim. The finishing pieces are what separate the outfit; a black leather jacket is a must-have, like this Belstaff one with snap buttons ($1,450), and a dapper checked cap in a textured wool blend ($24) adds just the right gentlemanly touch.
Photo credits: Women: First Lady Chic: Top left, Target Brands, Inc.; Bottom left, REED KRAKOFF LLC; Top center, Lord & Taylor; Bottom center, Nine West; Right, shopbop.com. Movie Star: Top left, mytheresa.com; Bottom left, Zappos.com; Center, NET-A-PORTER.COM; Top right, Planet Blue; Middle right, Zappos.com; Bottom right, Matches. Men: Dandy CEO: Top left, MRPORTER; Bottom left, Neiman Marcus; Top center, Bose Corporation; Bottom center, French Connection Limited; Top right, STYLEBOP.com; Bottom right, J. Crew. Jet Setter: Top left, Topshop USA; Bottom left, SINGER22; Center, Sunglass Hut; Top right, Sierra Trading Post, Inc.; Bottom right, Zappos.com