The lost art of '90s airport style + warm-weather vacay packing.

Travel-wear for your upcoming hot trip (manifesting one for you).

Feb 02, 2024

How do you airport outfit?

Denzel Washington in Yankees cap and belted denim; Winona Ryder in black suit & white tee, carrying a kids’ suitcase; Whitney Houston in high-tops & straw hat…The list goes on and on of epochal (see me trying out words besides the dreadfully overused “ic*nic”) airport outfits worn by celebrities. But the airport get-up sightings are diminishing as the gap between celebrities and riffraff like us normal people continues to grow. Celebrity private fliers may wish to set a style tone by posting pictures of their in-flight fit to their social media, but I refuse to include private jet outfits on my mental moodboard, for obvious reasons. The previously commonplace inspirational “airport outfit” has become a more rare occurrence, given the famous & uber-wealthy share little to no spaces with the public. But who really needs to be dictated to on wardrobe by celebrities, anyway—especially these days when it feels like they’re more out of touch with the average person’s life than ever before? Why not be the ‘90s celebrity of your own life, and dress like all eyes are on your plane-exit look?

Similar to my fascination with mixing sleepwear & regular clothes to run errands, I love the confused nature of an in-transit uniform. Maybe the layers don’t totally make sense; maybe there’s an out-of-place, but-essential-to-the-look, accessory; or maybe it’s a totally put-together luxe lounge ensemble, à la Lily van der Woodsen. If you’re anything like me, it’s a little nonsensical, yet methodical, and always in the camp of #nocheckedbags.

Since I was just on vacation in Puerto Rico, I’m going to walk you through the best categorical items to bring on your next warm getaway, and how they’re intertwined with your airport style. Also, my last post on trousers was hyper-technical, so let’s keep it light this time around with a little light-packing & styling advice! Side note: I’m a backpack & carry-on suitcase traveler, but I’m in the market for a better version of both—however I’m obviously a clothes+shoes person, not luggage, so if you have recommendations for me on bags, I’m all ears.

While I relate deeply to wanting comfort on a flight, I’m anti-athleisure or shlubby all-sweats outfits on a plane—you’re in public, c’mon now. And there’s nothing worse than bare feet or shorts on a plane, as Larry David displays in Curb with his (of course) confrontation with a stranger wearing shorts. That being said, there’s a way to wear a “real” outfit and still be comfortable.

For my in-flight fit, I opted for a lighter-weight cotton sateen pinstripe pant (mine are second hand Joseph trousers) because it’s a wrinkle-resistant fabric & cotton is the most breathable fiber. And given my pants’ navy-hue, they’re seasonless. Layers are a travel necessity, so I went for my favorite vintage Mickey Mouse pique cropped V-neck T-shirt + oxford men’s button-down over top, and a hoodie over top that. For footwear, as we all know, you must wear your heaviest shoes instead of packing them, and mine happened to be sandals—but I wouldn’t be caught dead without socks accompanying them at the airport or on a plane.

From cold→hot climate airport outfit recipe:

Breathable woven pant: cotton sateen, twill, or cotton/linen
T-shirt: boxy fit for breathability
Layered button-down or cardigan depending what you packed to wear w/ it OR a blazer, if you feel so inclined to bring to a hot climate (keep it linen, if so)
Hoodie: If you sleep on a flight, the hood makes all the difference for comfort/warmth/covering your face from the air/light
Chunkiest shoes (if sandals, include socks, for the love of God)

Similar to my airport outfit links below:

Get to packin’.

So we’ve covered your airport fit, but I’d like to recommend some packed items, too, with a focus on the non-functional items, naturally. I trust you all know your way around bringing the basics like socks, underwear, t-shirts, sleepwear, and swimsuits. But for dinners out or tourist-exploring, these are my tried-and-true hot climate clothes.

1. The calm before the storm 2. It's windy as hell 3. I've accidentally flashed ppl driving by

L.B.C.D.: Little Black Cotton Dress.

Cotton is breathable and lightweight and a poplin weave has its own kind of wrinkle-resistance. I love my Ellery smocked bodice poplin mini (remember how designed smocking, i.e. all-over on a bodice is great, but that cheap placement smocked chunk at the back of some dresses is a no-go). Smocking is an easy hot-temperature pick because you don’t have to fuss with zippers and it’s fitted without being constraining. An LBCD pairs great with a strappy sandal and a be-extra silk headscarf. Although the night I wore my LBCD to dinner, we did walk home and it happened to be the windiest night I’ve ever experienced, so I subsequently (& unintentionally) flashed passerby lol.

(Hi Ryan)! I'm wearing made in NYC Villeine shortalls + sneakers + bandana & accoutrements

Jump into jumpsuits.

Having learned my lesson after flashing half of San Juan the night prior (I discovered the locals refer to the area we stayed, in Condado, as “a window to the sea”, which opened my heart to find the wind romantic, instead of just super annoying:), I wore my trusty Villeine Roy shortalls the following day. We explored the incredible fortress, Castillo San Felipe del Morro, built in 1539, and walked around Old San Juan. My jumpsuit choice served me well in the wind & heat, and if the Roy Shortalls aren’t for you (can’t imagine why that would be)!, I recommend rompers (I do so hate word) that are unfitted and breathable. Shortalls can serve as your dress substitute: relaxed enough to feel like a dress, but protective and stable enough over your legs for those unpredictable winds. If you go for a long pant option, ensure the fabrication is extra lightweight—and whether it’s shorts or long, cotton or linen (flax) fiber content is the way to go for hot weather.

1. Hi Andrew in the background! 2/3. No we didn't eat at Wendy's but we did want a frosty & they were closed :((

Include a separates look.

I always like to include a “going-out” outfit that isn’t just a dress because you can mix the separates back in with other items for different occasions. And lo and behold, we arrive at my favorite skirt style again: the kilt/wrap. I brought my secondhand Burberry cotton twill wrap skirt. Remember wrap skirts are often adjustable so they provide ease of fit at the waist after a meal, etc. Oh! And I almost forgot: don’t fear packing white clothes; they’re so easy to clean with bleach—BUT pack them in a plastic bag for protection. Lastly, per usual, given my defense of “going-out” woven tops and silk blouses, I brought my Jacquemus cropped button-down with braided+corded strap at the back. This one’s a viscose crepe-de-chine; not the most breathable—but more so than silk, and cropped enough for me to not care on a breezy eve.

I'm wearing eyelet Gigi Hadid x Frankies Bikinis bikini + vintage Laura Ashley nightie

Gauzey waistline-free cotton dress (w/ an accompanying white bikini).

OK so I got zero photos in my white dress (there it is in the bottom corner of the first pic, jAcuZZi-side, though) but I’ve included the original photo (center) from the Poshmark seller lol. This one’s a no-brainer—wear it as a beach cover-up, like I did, or a regular dress and embrace the sheerness. I’m obsessed with my vintage Laura Ashley cotton voile (voile is a super-lightweight fabrication) dress—it gives a perfect nightie-in-which-I-haunt-you vibe. I think it was originally a nightgown, anyway. If you’re looking for something similar, use “vintage cotton nightgown” in your search terms—there’s so much good stuff. And if you want my Frankies Bikinis swimsuit in raspberry, I’ve linked it here for the top, here for the bottoms.

Other misc. outfit essentials.

Jean shorts & rib knit tops/dresses. Rib knit fabric is a great way to look like you’ve tried when you haven’t. It’s fitted but comfy, and easy to tuck in. I love Cotton Citizen for organic cotton, made in USA items (brought my one-shoulder tank from them), and Simon Miller does a handful of great rib knit items which you can also easily find secondhand via The Real Real. And for jean shorts, I packed my trusty, long-hemmed, self-cut Levi’s ‘550s.

To souvenir clothe or not to souvenir clothe?

I’m not easily persuaded to purchase souvenir clothing (I do have the tendency to collect—let’s call them trinkets, instead of random junk—wherever I travel) but when I walked past this perfect tie-dyed iguana-print T-shirt, I knew I had to have it in an XL and wear it as a dress *chef’s kiss*. Maybe I’m riding the tourist-clothing wave since London because it was there that I similarly couldn’t resist a Union Jack hoodie (as you may have picked up on: I packed it with me to PR)—I swear, said sweatshirt was my first endeavor into tourist apparel. But now my thought is, if you’re on vacation, indulge in a stupid t-shirt and look like a f*cking tourist—you literally are one.

Wishing for you a warm upcoming holiday, wherever that may be—I had the privilege in beautiful Puerto Rico. xHannah