I'm Making Room in My Suitcase for These 9 Vacation Outfits Inspired by Street Style

If you're reading this, it means I'm currently in Italy for the 2026 Winter Olympics. I've had this trip planned for months, which means I had time to really consider my packing strategy. In the end, I landed on nine New York-coded outfits that can carry me through my 20-day vacation.

I didn't intend on wearing all-black in Milan (and London, where I'll be spending some time), but I'm born and raised in the Big Apple, so it's practically in my blood. I made sure to include some other trendy colors in my suitcase, though, including on-theme navy blue and bright lemon yellow. But I'm relying on (mostly) neutral pieces that can be teamed together in a myriad of ways. Every single item in my suitcase has something in common: It's available to shop at Nordstrom, Zara, and J.Crew.

Ahead, see the NYC It Girl inspiration permanently on my mood board now guiding my vacation outfits. From sporty track pants to a luxe faux-fur coat, these are all end-of-winter style essentials I can't wait to wear abroad.

All Black (With a Touch of White)

Break up your monochromatic black outfit with a single contrasting piece. Layering a white scarf over your top is an elegant way to do so; I'll also be swapping my usual black crossbody for a zebra-print bag.

Preppy Neutrals

I'm trying to avoid wearing red, white, and blue outright, so I'm leaning into American prep vibes instead. Corduroy trousers are a winter-appropriate piece. Crewneck knits and long wool coats to round out the vibe.

A Statement Coat (And Little Else)

Sometimes, the coat is the outfit. Style this faux-fur one over an otherwise simple, fitted look, and let the jacket do the talking.

Mad For Plaid

Plaid was my favorite fall trend, and I'm not ready to let it go, so it was a natural inclusion on this list. It's a little punkier than the other looks here, and breaks up my normally pattern-free rotation. Keeping the rest of the pieces simple lets the plaid shine.

Feeling Blue

Cool blue is my favorite light-hued neutral, but navy is also flooding my wardrobe in 2026. Pops of lemon yellow keep it feeling unexpected.

Hi, Contrast

I'm leaning into the après-ski vibe of the Winter Olympics with a cropped white jacket. Cosplay as a skier with a knit hood and athleisure-coded layers.

Elevated Jeans

It's going to be a little warmer in Milan than in New York (and thank goodness for that!), so I have the chance to pull out my lighter spring jackets and light-wash denim. J.Crew does the former category particularly well; I'm relying on my classic Levi's jeans to keep the look casual.

A Touch of Print

I've been on a white denim kick ever since Style at Large contributor (and one of my favorite follows) Larissa Mills talked about the category in a recent column. To make it feel more "me," I'm leaning on a cheetah-print jacket and red accessories.

Modern Draping

I'm only five-foot-two, so I rely on elongating silhouettes a lot. Enter: this lace-trimmed tunic. With an oversized blazer, it feels incredibly elegant.