A bright blue turtleneck, high-rise leggings in rich brown and black knee-high boots make a travel outfit feel finished before you reach the gate. The idea is one clear color on top, a soft neutral below and black at the feet, with a single black weekender to carry it all. These are fresh pieces for that look: the blue boxy turtleneck, the high-rise leggings, the low-heel black knee-high boots and the black canvas weekender.
Travel day: straight from the flight to lunch at the Four Seasons in Cabo.
Pull the turtleneck over the leggings and let it skim the hip. Tuck the leggings into the boots for one clean line below the knee, then carry the weekender by hand or on its shoulder strap. The colors are meant to be mixed: blue on top, a warm neutral through the legs, black at the feet.
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The Ruched Crewneck Tops I Buy in Multiples
I have eight of these long-sleeve, stretchy, double-lined crewneck tops with ruching on the sides: four in black and four in white. The side ruching is very flattering, and these tops are versatile for everyday wear. I love them that much. I find the fit so flattering, and I get so many compliments when I wear one. It is a really well-priced piece that I use for workouts, beach walks and travel, and as an underpinning on ski trips.
It runs small. I usually wear a small, but I bought a medium because it is a tight fit, so size up. For me, this is the best top to buy in multiples. ruched crewneck long sleeve top – get it here.
If you prefer stretch cotton, Skims has a fitted Cotton Jersey Long Sleeve T-Shirt in Soot. Browse the cotton long-sleeve T-shirt.
Everlane Boxy Turtleneck in Soladite Blue
A saturated blue turtleneck gives the outfit its color. The boxy shape is roomy through the body and cropped at the hem, so it sits neatly over high-waisted leggings and keeps the top half easy on a long travel day.
Athleta Salutation Stash High Rise Legging in Truffle
The original leggings are sold out. These full-length, high-rise leggings in Truffle are a similar brown-toned option, with side pockets for a phone or small essentials. Browse the brown high-rise leggings with pockets.
STAUD Wally Flat Boot in Black
A black knee-high boot is the sharper part of this otherwise soft outfit. The Wally Flat has a low 25mm heel rather than a tall heel, so the silhouette feels dressed without turning the airport into an occasion for stilettos. The brand notes a narrow fit. I would let the leggings disappear into the shaft and keep the sweater untucked.
BÉIS The NEW Weekender in Black
One black bag keeps the look simple. The canvas weekender has a convertible bottom compartment, a 16-inch laptop sleeve and 42 liters of space, which makes it enough for a short trip.
Shop the full collection: buy it here
Photo credit: Everlane
Photo credit: Athleta
Photo credit: STAUD
Photo credit: BÉIS
Photo credit: Banana Republic Factory
Photo credit: Veronica Beard
Photo credit: Portland Leather Goods
Photo credit: Jenni Kayne
A Tan Trench for Travel Days
The original trench is sold out. This Timeless Trench Coat in Maverick Tan is a similar light layer over a knit for the flight and jeans at the destination. Browse the tan travel trench coat.
Veronica Beard Beverly Skinny-Flare Jean in Indigo Rinse
For a leg-lengthening option, the Veronica Beard Beverly skinny-flare jean in Indigo Rinse is the one to wear on the plane home: high-rise, fitted through the leg with a flared hem, in a soft stretch denim that keeps its shape through a long travel day. It works with the same boots and knits. buy it here.
A Small Brown Leather Bucket Bag
The original suede tote is sold out. This Small Bucket Bag in Coldbrew is a similar drawstring day-bag option, with an adjustable crossbody strap and interior pocket. It is smooth leather, not suede. Browse the small brown leather bucket bag.
A Classic Cashmere Crewneck
For a travel-day knit that works on the plane and at dinner, a classic-fit cashmere crewneck from J.Crew is an easy base layer.
How I would wear it for the flight
Keep the sweater loose over the leggings and let the black boots create one clean line below the knee. Carry the weekender in your hand or on its shoulder strap rather than adding another large tote. If the cabin runs warm, a light layer you already own under the sweater makes it easier to adjust without changing the whole outfit. Wear comfortable socks inside the boots, and keep anything you need at security easy to reach.
The useful investment is the piece you will wear beyond the flight. The sweater works with jeans at the destination; the boots can go straight to dinner. The leggings do the close-fitting travel work. Pick one bag, not both, and leave room for what you will actually carry.
The real test of what to wear on travel days is lunch at the destination. We had lunch at the Four Seasons in Cabo, the kind of midday meal where an easy knit, leggings and boots still feel right at the table. No costume change, no second outfit to pack.
Jenni Kayne Shearling Moroccan Slipper in Smoke
A packable shearling slipper is the piece that makes a long travel day feel like home. The plush shearling upper and suede outsole keep it light in a tote, and the folded back heel means it wears like a mule in the cabin or a closed-back slipper at the hotel.
For more travel-day basics in the same spirit, see this canvas weekender bag and these high-waisted black leggings.
Finally, for the bag and suitcase, see my guide to the best carry-on suitcases.
Reader favorites right now: how to style the L.L. Bean Boat and Tote for fall, Beth Dutton coats and boots, and the DÔEN warehouse sale guide.
Shop the Post
- Everlane Boxy Turtleneck in Soladite Blue
- Salutation Stash High Rise Legging in Truffle
- STAUD Wally Flat Boot in Black
- BÉIS The NEW Weekender in Black
- Timeless Trench Coat in Maverick Tan
- Veronica Beard Beverly Skinny-Flare Jean
- Small Bucket Bag in Coldbrew
- Jenni Kayne Shearling Moroccan Slipper
- classic-fit cashmere crewneck
