How Do I Style Winter Looks for the Whole Family?

Family dressed in cosy winter outfits for a holiday trip

Winter holidays with family is a whole mood! And never calm. Someone’s suitcase is already full. Someone else hasn’t started packing. Mom keeps reminding – Carry something warm! Dad’s looking for a jacket he last wore in 2009! Kids want their favourite outfits only. Even if it is not practical. Everyone is already in holiday mode. And you’re standing there trying to make outfits work for weather, photos, comfort, and ten layers of unsolicited advice. Whether it’s a trip to a hill station. A cosy staycation. Celebrating Christmas overseas. Or visiting relatives. Winter travel is about dressing smart, comfy, and cute! This season, Westside helps you sort winter holiday style for the whole family. Men. Woman. And Kids. Minus the packing drama.

winter-wear_for_men - Westside

So what do you actually wear on a winter family holiday?

Layers. Always layers. Because winter days love switching personalities. Crisp morning. Sunny afternoon. Chilly evening. Freezing nights. You need outfits that can keep up without requiring five outfit changes. And zero drama. Soft knits. Cosy jackets. Relaxed trousers. And easy dresses layered with warmth. Comfortable enough for long travel days. Stylish enough for all the pictures your family will force you to take!

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What should women pack for winter holidays?

Pieces that look put-together without trying too hard. Warm dresses you can layer. Knits that feel soft, not bulky. And jackets that works with everything. Because you know winter holidays! They usually involve a lot of walking. Sightseeing. And definitely lots of sampling new food items. You want clothes that don’t restrict you but still look great when someone pulls out a phone and says, “Group photo!”

winter-wear_for_kids - Westside

And what about men?

Men, this is not the time to rely on one hoodie for the entire trip. Winter holidays call for smart layering. Jackets that instantly upgrade the look. Smart sweatshirts. Trendy sweaters. Or funny Christmas sweaters. We totally vibe with that. Soft knits. Chinos that feel comfortable but still look sharp. And trousers that don’t feel stiff after hours of sitting!

Okay… but kids are the real challenge, right?

Always. Kids want comfort. Warmth. Easy to move in. And their favourite outfit only. Winter holiday outfits for kids need to be cosy. Playful. And practical. Think soft fabrics. Easy layers. And pieces that don’t make them feel restricted. Photo-ready but warm enough to keep parents from panicking every five minutes.

Any packing tips before the suitcase chaos begins again?

Pack versatile pieces. Choose items that mix and match easily. Always add one extra cosy layer. Someone will need it. And trust us, future-you will be grateful when the temperature drops unexpectedly.

Winter holidays are about shared moments. Long walks. Hot drinks. Loud conversations. Too many photos. And memories that stay long after the trip ends. With Westside, dressing the whole family for winter feels easy, comfortable, and stress-free. Exactly how holidays should be!

Shop winter holiday styles for men, women, and kids at Westside in-store or online. Because family trips are chaotic enough! Your outfits don’t have to be!