A Cozy Travel Outfit That Actually Works (Learned From Experience)

My husband planned a surprise girls’ getaway in Park City for my birthday this year, and I’m still smiling about it. He coordinated everything—my sister flew in from D.C., my sister-in-law came in from Denver, and we all met in Salt Lake City for a weekend that basically checked all my favorite boxes: eating, shopping, Utah mountains, and the spa.

We landed early in the morning and headed straight to Beaumont Café in Millcreek for brunch. Because I knew we were hitting the ground running, I wanted to look cute coming off the plane… which led to a travel outfit mistake I will not be repeating.

I wore jeans. And not just jeans—a pair of heeled boots, too, because I didn’t have enough room in my suitcase to pack them. I thought I was being strategic; instead, I spent two hours on a plane wishing I had chosen literally anything else.

The minute we got to Park City, I realized:

• Jeans = cold
• Jeans = stiff
• Jeans = absolutely not worth it for winter travel

That night, I completely rearranged my suitcase so I would not have to fly home in heels again. And on the return flight? I wore the coziest, warmest, most comfortable outfit—one that still looked polished enough that I could’ve gone straight to brunch again.

Now it’s officially my go-to winter travel outfit. Here’s the formula.

---

1. Start With Soft, Comfortable Bottoms

This is the non-negotiable. If I learned one thing from the flight to Salt Lake, it’s that traveling in jeans in winter is a guaranteed regret.

I’m not a big fan of flying in leggings either—they’re fine for quick flights but not my favorite for sitting for hours. Instead, I’ve become obsessed with loose, flowy trousers or polished jogger-style pants that look like real clothes but feel like pajamas.

Look for bottoms with:

• A stretchy waistband
• A comfortable, drapey fabric
• A little room to breathe
• A silhouette that still looks intentional

adidas has some great options that hit that balance of “structured but soft”—you get the polished look without sacrificing comfort.

---

2. Add a Matching Fleece Top or Sweatshirt

Winter flights can be cold, and a warm layer is always the answer.

A matching fleece set looks instantly intentional—even when the reality is you slept four hours, chugged a smoothie on the way to the airport, and barely made your flight.

Choose neutrals like charcoal, cream, brown, or camel for a sleek, travel-friendly palette.

If you don’t want a full set, pair your comfy bottoms with:

• A fitted long-sleeve tee
• A chunky knit
• A cozy cashmere sweater

The key is keeping the colors cohesive so everything layers well. I like to go full matching OR pick a tonal look.

---

3. Choose Sneakers You Can Walk (and Travel) In

Let’s revisit the boot situation. Wearing heeled boots on the outgoing flight was… a choice. A choice I regretted a few hours into travel.

On the way home, I wore my neutral adidas sneakers, and it was a dream.
Comfortable. Breathable. Easy to walk in. Easy to style. May sneakers never stop having a moment.

For travel I’d stick to neutral colors—cream, taupe, black, or brown—so they go with everything in your suitcase. But, I also consider animal print a neutral and sometimes a deep cranberry or olive will work with everything, too. Often times I end up in my workout shoes for the flight because they’re the biggest footwear I need to pack.

---

4. Add One Warm Layer & a Hands-Free Bag

Winter travel means constantly adjusting to different temperatures: the chilly terminal, the overheated plane, the cold air outside.

I like a warm outer layer that’s easy to take off and stash away:

• A wool coat
• A lightweight puffer
• A long trench
• A thick cashmere wrap

For bags, I’m firmly team hands-free:

• Belt bag across the chest
• Backpack if I’m flying with kids
• A bigger tote if I’m carrying extra snacks (or just couldn’t fit everything in my carry-on)

---

5. Finish With Simple Grooming Touches

It’s amazing how much more put-together an outfit feels when you add the smallest bit of polish. I’m not doing full glam at 6:30 a.m., but I will take two minutes for:

• Concealer under the eyes
• Mascara
• Hydrated, glowy skin
• Lip balm
• Hair in a sleek ponytail, braid, or low bun

Clean-girl makeup + comfy clothes = elevated travel aesthetic. Plus, if you skip the foundation in the morning, you can apply some when you land, and you’re set for the rest of the day.

---

The Cozy Winter Travel Uniform (You Can Copy This)

This is the outfit I’ll be wearing for pretty much every winter flight going forward—warm, comfy, polished, and realistic for travel days:

• Loose, flowy trousers or swats with a stretchy waistband
• Fleece sweatshirt or matching fleece set
• Neutral sneakers (love these ones right now)
• Minimal jewelry
• Tote bag
• Warm wool coat or lightweight puffer
• Clean-girl makeup + simple hair

It’s comfortable enough for a long flight, cute enough to head straight to brunch, and flexible enough for whatever your first-day plans look like.

---

Final Thoughts

My Park City birthday trip was the best birthday gift—time with my sisters, great food, shopping, those gorgeous mountain views, s’mores by the firepits, and the kind of long, slow conversations that only happen on girls’ trips. Cannot wait ’till the next one.

And from now on, I will not fly in jeans.