When it comes to mastering the art of the travel wardrobe, it’s no surprise that our favorite fashion insiders also moonlight as packing pros. In My Packing Style, we tap some of the most well-traveled people we know for a peek inside their travel bags and vacation wardrobes to see how they take their style on the road.

You’ve bookmarked the trip, you’ve screenshotted the outfits; now, a look at how it all comes together.

Not everyone can reach into their closet, grab what’s on top of the stack, and confidently throw it into a carry-on knowing it’ll work. Then again, Alyssa Wasko Stein isn’t just anyone. The Donni. founder has built a brand of coveted essentials around do-it-all styles in lively colors, prints, and textures that belong together without the need for overthinking.

Her main strategy, as she explains it, is to pack a few basics she can mix and match, then add in accessories to create interest and give her looks a personal feel. A short gold chain brings balance to a long charm pendant, while a black leather pouch from The Row works overtime to organize sundry items in her travel tote, doubling as an evening purse when the occasion calls for it.

A generously sized weekender is her go-to for short trips, sometimes even in place of a carry-on. In it you’ll find everything from a cozy scarf and an oversized sweater to ward off cabin chills (she won’t risk feeling cold on a plane), to a rotation of small bags (she’ll always have room for a colorful suede clutch), and a collection of cherished jewels to elevate her capsule wardrobe.

We caught up with Wasko Stein as she returned from a work trip in Telluride, Colorado, and had her give us a peek into her bright red Kallmeyer tote. “Can all work trips be in Telluride? Asking for a friend. I am from Colorado so this was a real treat; I will be back,” she adds.

Are you a pre-packer or a throw-in-and-go type?

I typically do it the night before; it’s my version of living on the edge.

Do you pack in outfits?

I don’t! I usually pull things that are in my current rotation or that I feel excited to wear and hope for the best that they’ll come together when I arrive to my destination. I love the colors on this baseball tee, and this slinky V-neck is so special. It took us such a long time to get right—it reminds me of vintage St. John.

What’s your go-to brand for vacation dressing?

My wardrobe is mostly Donni. and vintage. The only jeans I wear that aren’t vintage Levi’s are Still Here’s Life jeans. For bathing suits, I love Eres.

What’s your go-to travel bag right now?

Kallmeyer’s Cottage Tote. It’s more than a weekender. It has room for everything I need—sometimes I don’t even bring a carry-on. Also, it’s great when I’m traveling with my kids as it fits so much.

Do you have a travel outfit formula?

Generally: a knit pant, an oversized button-down, and a sweater with a loafer.

What are your in-flight nonnegotiables?

Comme Si socks—they have a little sheen to them which adds the perfect finishing touch to anything from Keds to loafers—and a travel wrap or scarf. I am terrified of being cold on a plane.

Team travel scarf or travel sweater?

Both! They do different things and sometimes you need both.

What is your vacation beauty product MVP?

Solara sunscreen.

Do you have a strategy for approaching accessories?

I like to have an assortment, so this is the department I usually pack the most in. My main strategy is to bring things that don’t overlap. For example, necklaces of different lengths and colors, and bags of different sizes and shapes. That way you have better odds of something working out. Thistles’s The Suede sunglasses are also a current favorite.

Travel steamer: Yes or no?

I generally expect there will be a steamer on the other side, and if not I bring one! Natural fibers generally wrinkle and are the majority of what I wear, so steaming is so important. It’s worth the extra step. Also, I find steaming therapeutic.

What has been your most-worn vacation item?

For warm weather, my Christopher Esper flip-flops. For cold weather, our Italian cashmere sweaters (they’re coming out in November).

What staple piece is always in your suitcase?

It’s a tie between a white T-shirt and a blue oxford button-down. When things aren’t working out, both of those are safe and ground things—call it packing insurance policy.

Overpacking or leaving room for souvenirs?

Overpack. I tend to feel the need to fill the suitcase.

What’s the best packing lesson you ever learned?

Never check a bag.