10 Outfits For Winter Travel

Meghan in Paris Winter Outfit Arc de Triomphe

Planning winter travel outfits can feel tricky. You want to stay warm, comfortable and practical for long days of exploring but you still want to feel pulled together for café stops, museum hopping and cozy dinners out. Over the years, I’ve perfected a winter travel wardrobe that balances style and function — built around timeless pieces, smart layers and shoes you can actually walk in.

Whether you’re headed to Paris, London, New York or a charming European countryside escape, these outfits will take you from travel day to sightseeing to dinner without missing a beat. Best of all, I’m using brands and silhouettes I already love and wear regularly so these are truly tried-and-true combinations.

Below are 10 chic winter travel outfits that mix comfort, polish and versatility — perfect for packing light while maximizing outfit potential.

10 Outfits for Winter Travel

Outfit 1: Elevated Travel Day Look

Perfect for: Airport days, train travel, long drives.

This is my go-to formula for travel days when comfort is key but I still want to feel put together.

Wear:
– Soft knit sweater
– Straight-leg jeans
– Wool coat
– Streamlined or sporty sneakers
– Crossbody bag
– Oversized scarf

Why it works: Layers keep you warm without overheating, sneakers make security lines easy and a tailored wool coat instantly elevates the look.

Trousers + Converse

A go-to day to day look for me in winter is a favorite pair of trousers. It’s also one I repeat often for travel days.

I’ll often wear trousers with Converse sneakers but also ballet flats.

Outfit 2: Classic Paris Sightseeing Uniform

Perfect for: Museums, walking tours, café hopping.

If I had to choose one winter sightseeing outfit, this would be it.

Wear:
– Striped sweater
– Tailored black trousers or leather pants
– Longline coat
– Sneakers

This outfit feels timeless and French without trying too hard. It easily transitions to evening if you sub out a different shoe as well.

Outfit 3: Cozy Layers for Cold Days

Perfect for: Extra chilly weather, outdoor markets

Wear:
– Cashmere crewneck
– Slim straight jeans
– Wool coat
– Loafers with sheer socks

Outfit 4: Smart Casual for Lunch Dates

Perfect for: Casual lunches, shopping days.

Wear:
– Cashmere crewneck layered over a tee
– Straight-leg jeans
– Longline coat
– Heeled Boots
– Shoulder bag

This is one of my favorite formulas for travel days when you want to look chic but not overdressed. Add a beanie or a large scarf for added warmth.

Outfit 5: Chic Dinner Outfit

Perfect for: Restaurant reservations, wine bars.

Wear:
– Slip skirt
– Knee-high boots
– Tailored blazer
– Mini bag

Slip skirt not your vibe? Consider a sweater dress instead.

Outfit 6: Casual Cool Coffee Run Look

Perfect for: Morning coffee and pastry run, strolling neighborhoods.

Wear:
– Relaxed sweater
– Drapey trousers
– Sporty sneakers
– Trench or wool coat
– Baseball cap

This is my off-duty uniform. It feels effortless and cool while still being polished enough for city exploring.

Outfit 7: Polished Day-to-Night Look

Perfect for: Full sightseeing day into dinner.

Wear:
– Fitted turtleneck or cashmere sweater
– Straight leg jeans
– Ankle boots
– Oversized wool blazer
– Versatile bag

This outfit transitions beautifully. During the day it feels practical and chic. At night, add a fun earring or a swipe of lipstick and you’re set.

Outfit 8: Travel-Friendly Suiting

Perfect for: Business trips, meetings, city exploring.

Wear:
– Tailored blazer
– Matching trousers
– Layering camisole
– Kitten heels
– Structured tote

Choose fabrics with stretch so you can move easily. I think M.M.LaFleur does the best suiting options because their fabrics and fit are impeccable.

Outfit 9: Weekend Getaway Look

Perfect for: Countryside trips, cozy inns and small town exploration.

Wear:
– Chunky knit sweater
– Straight-leg jeans or barrel jeans
– Lug sole boot
– Quilted jacket or wool coat
– Wool scarf and beanie

This is perfect for Cotswolds-style trips or snowy mountain towns. Cozy, casual but still well thought out.

Outfit 10: Minimalist Capsule Staple

Perfect for: City exploration.

Wear:
– Striped knit
– Wide leg jeans
– Long wool coat
– Ankle boots with a kitten heel

This is an easy look to put together with what you likely already own in your closet. It’s built on wardrobe staples that feel timeless and yet incredibly easy to mix and match.

Winter Travel Packing Tips

Stick to a Neutral Color Palette

Black, camel, cream, navy and gray all mix seamlessly. This lets you rewear pieces in different combinations without looking repetitive and ensures your packing is a bit easier.

How I Plan My Outfits for Travel

Choose Shoes Wisely

I (usually) try and pack no more than 3-4 pairs.
– Comfortable walking shoes
– Dressy boots
– Optional flats – ballet flats or loafers

Layer Smart

Thermal base layers, thin knits and scarves are key. This lets you adjust easily between cold outdoors and warm interiors.

Prioritize Fabrics

Wool, cashmere and merino are warm without bulk and resist odors. Perfect for rewearing on longer trips.

Why These Outfits Work for Winter Travel

Each of these outfits is built around timeless wardrobe staples I already wear regularly. Instead of packing trendy pieces that only work once, focus on:

• Great outerwear
• Quality knitwear
• Comfortable shoes
• Tailored basics

These items mix and match effortlessly so you can create dozens of outfits from just a few core pieces.

Shop My Favorite Winter Travel Brands

Some of my go-to brands for winter travel style:

Toteme (outerwear and elevated accessories)
Sézane (knits and blouses and outerwear)
Jenni Kayne (elevated basics and knitwear)
Veronica Beard (blazers)
La Ligne (sweaters)
Aritzia (trousers; minimalist staples)
Soldout (layering pieces)
Agolde (jeans)
Margaux (footwear)

Shop for Winter Travel Outfits

I’ve invested in these over time and they continue to earn their place in my suitcase season after season. If you’d like even more guidance, check out my guide to Wardrobe Staples I Always Reach For (inclusive of where I shop for them).

. . .

Winter travel doesn’t mean sacrificing style for warmth. With a thoughtful capsule wardrobe and smart layering, you can feel comfortable and confident everywhere you go — from long travel days to candlelit dinners abroad.

These 10 winter travel outfits are tried, tested and truly wearable. They photograph beautifully, pack easily and work across destinations whether you’re strolling Parisian streets, hopping between London neighborhoods or escaping to the countryside.

If you’re building your own winter travel capsule, start with great outerwear, comfortable shoes and quality knits. Everything else will fall into place.

En Route to Rêverie