MomSkoop
Packing for holiday travel doesn’t mean choosing between style and comfort.
With the right combinations, you can look put-together while feeling relaxed from takeoff to touchdown.
Whether you’re heading to a snowy cabin or exploring a new city, these outfit ideas prove you can stay cozy and chic at the same time.
1. Trench Coat and Hoodie
A hoodie becomes instantly sophisticated when topped with a classic trench coat, creating an outfit that moves seamlessly from airport terminals to city streets with polished ease.
Tailored trousers and clean white sneakers keep the look balanced and comfortable, offering a refined vibe without feeling overworked, while the layers make it easy to adapt as temperatures shift throughout the day.
Even once you remove the trench on the plane, the hoodie-and-trouser pairing still feels intentional, and the cushioned sneakers keep you supported through security lines, gate changes, and every unpredictable moment of holiday travel.
2. Chunky Sweater and Easy Pants
Comfort meets elegance when you pair an oversized knit sweater with soft, flowing pants, especially wide-leg silhouettes in breathable, wrinkle-resistant fabrics perfect for long travel days and easy movement.
The cozy knit adds warmth and texture without feeling bulky, while the loose trousers and classic loafers create an effortless yet intentional look that’s polished enough for airport cafés or train platforms.
Because the pieces transition seamlessly from travel mode to dinner reservations or early exploration, this combination is ideal for arrival days when you want to feel put-together the moment you step off the plane.
3. Track Pants and Mary Janes
Track pants have officially entered the fashion conversation, and pairing them with Mary Jane flats—complete with cozy socks peeking out—creates a mix of athletic comfort and unexpected polish that feels fresh and modern.
The structured shoes elevate the relaxed vibe of the pants, proving that casual doesn’t have to mean sloppy and adding a playful twist that stays stylish without drifting into overly trendy territory.
Ideal for travelers who want maximum comfort without sacrificing aesthetics, this combination keeps you feeling good from departure to destination while still looking intentionally put-together.
4. Leggings and Oversized Jacket
Leggings get an instant style upgrade when paired with an oversized leather or bomber jacket, creating a balanced contrast between the fitted bottom and relaxed top that gives off effortless cool-girl travel energy.
Choosing high-quality leggings with structure keeps the look elevated rather than athletic, while the roomy jacket adds warmth, edge, and a bit of camouflage for any in-flight snack bloat, especially when finished with sleek sneakers or ankle boots.
The result is an outfit that delivers true off-duty model vibes without sacrificing practicality, keeping you comfortable through every leg of your journey while still looking intentionally put-together.
5. Relaxed Jeans and Crewneck Sweater
Sometimes the classics win for a reason, and straight-leg or loose-fit jeans paired with a timeless crewneck sweater create a simple, reliable travel uniform that never feels outdated or overthought, especially when finished with clean leather loafers.
The key is choosing denim with a comfortable fit that won’t pinch during long sits and a neutral crewneck that layers easily, giving the whole look a clean, intentional feel that leans effortlessly elegant.
Whether you’re heading to grandma’s house or catching a flight to a new destination, this combination adapts to every plan with zero fuss and maximum comfort.
6. Sweatsuit and Sneakers
A matching sweatsuit might sound casual at first, but when styled with intention, it becomes one of the chicest and most practical travel outfits you can wear, especially in neutral or muted tones paired with minimal sneakers and simple gold jewelry.
The key is choosing a tailored set that fits well and looks fresh rather than worn out, then elevating it with small touches like a structured bag or leather tote to give the entire look a polished feel.
With maximum comfort and none of the “just rolled out of bed” energy, this combination is exactly what holiday travel calls for.
7. Ball Cap and Wool Coat
Mixing sporty and sophisticated pieces creates a surprisingly polished travel look, especially when you pair a quality wool coat with relaxed denim, a classic baseball cap, and loafers or ballet flats for an outfit that feels both approachable and refined.
The structured coat adds warmth and intention, while the cap introduces a casual, unfussy touch that keeps the whole ensemble from feeling overly formal, making it ideal for days when you want to look presentable without putting in much effort.
Perfect for colder destinations, this combination offers real outerwear practicality while maintaining a laid-back, comfortable aesthetic throughout your journey.
8. Long Cardigan, Tee, and Soft Trousers
A long, flowing cardigan instantly elevates even the simplest pieces, especially when layered over a basic tee and paired with wide-leg trousers in a soft, breathable fabric that keeps your travel look cozy and refined.
Slip-on shoes like mules or loafers add ease without fuss, while the cardigan acts almost like a lightweight coat, offering warmth, visual interest, and complete freedom of movement so the whole outfit feels effortless and breathable.
Perfect for shoulder-season travel, this combination gives you layers you can adjust throughout the day, keeping your style polished no matter how the temperature shifts.
9. Knit Dress with Tall Boots and Scarf
For travelers who love one-piece dressing, a ribbed knit dress offers effortless warmth and style, especially when paired with tall boots that keep your legs cozy and a blanket scarf that adds both texture and extra comfort.
This combination feels intentionally polished without sacrificing ease, eliminating the need to coordinate separates while allowing the boots to transition smoothly from travel to exploring and the scarf to double as an in-flight blanket.
It’s a foolproof choice for days when you want to look pulled-together but don’t have the time or energy to plan multiple pieces, making holiday travel feel infinitely easier.
10. Puffer Jacket, Joggers, and Chunky Sneakers
When temperatures drop, a cropped or mid-length puffer jacket becomes the ultimate travel companion, especially when paired with tapered joggers and chunky sneakers for a look that balances warmth, mobility, and modern style without leaning too athletic.
The puffer delivers real insulation, the joggers keep you comfortable during long hours of sitting, and the sneakers add a fashion-forward touch while providing the support you need for navigating terminals or wandering cobblestone streets.
Ideal for cold-weather destinations, this combination keeps you warm, comfortable, and effortlessly stylish through every step of your journey.