As a single Mum who has spent years taking road trips with a teen, I consider myself something of an expert in choosing travel outfits. The key to a successful holiday wardrobe is to approach the issue less as a “leisure preparation” activity and more of a “logistical mission involving extensive diplomacy and negotiation”.
Whether we’re off skiing on a home exchange, or taking a road trip through California, the one thing I’ve learned is that the key to survival is packing smarter – not packing more.
This post outlines my hard-earned and wildly caffeinated guide to choosing the perfect travel outfits – all while keeping your luggage within budget and your teen (mostly) speaking to you.
What makes the perfect road trip outfit?
A good travel outfit has to be flexible – you might need to go from the airport to a scenic viewpoint, or jump off the train straight to dinner without looking like you’ve slept in your clothes.
That means we want soft clothes that don’t wrinkle easily, like jersey sweaters, soft tee shirts and cotton-blend trousers that can survive being sat on, slept in and crumpled in the back seat of a car.
No matter where we go, I’m always going to pack a few pairs of Tom’s Trunks trousers, multiple relaxed sweaters and plain tee shirts, and a lightweight jacket for warmth but also to make our look smarter when needed. Uniqlo is a great spot to pick up light cotton jersey jackets that are absolutely impossible to wrinkle, and pull together an outfit in minutes. What about outfits for teens?
In some respects, choosing the right travel outfit for teens is none of your business – my teen has zero interest in my opinions on fashion. But where I do have a vested interest is in what will literally fit into our luggage.
So start with timeless essentials that can be reworn and re-styled – neutral tee shirts, easy layers, and flexible cotton trousers or jeans will see you through cafes, hikes and unexpected Insta photo opps.
Don’t forget accessories. They take up almost no space but add personality and options. So you can wear the same clothes in lots of different configurations, creating endless outfit combinations.
Accessories are your secret weapon — they take up almost no space, but add personality and options. A printed scarf or statement earrings can transform the same outfit so even your teen won’t accuse you of “wearing the same thing again”.
Stealing celeb style inspiration
Teens have a keen interest in what their favourite celebs are wearing – Flea often adopts the tone of a patient teacher as she shows me why it’s important that jeans are baggier than clown trousers, or why it’s important to have a co-ord at the airport. But the principles are useful – oversized blazers, monochrome sets, co-ords and cool trainers – all achievable and road-trip friendly.
You definitely don’t need a designer wardrobe, because who has the time and money for that? Trust me, comfort is your best friend when you have had no sleep and you’re about to drive for hours while listening to your child’s chosen playlist.
What glasses work best for your face shape?
Because I’m officially old, my road trips now involve lots of squinting at road signs, asking Flea to read parking instructions, and trying to zoom in on Google maps.
The right glasses help you to see – and can combine as sunglasses! They’re also a good fashion detail – does anyone else think their face looks better in glasses? A quick guide to the best glasses for your face shape is:
- Heart-shaped: Aviator or square frames (great if you need to look assertive while telling your teen they can survive with 2 pairs of jeans).
- Oval: Most styles work; rectangular or geometric add definition.
- Square: Round frames soften the angles.
- Diamond: Cat-eye or browline frames balance your features.
- Round: Rectangular frames add structure.
- Triangle: Browline or cat-eye lift everything upwards — including your expression after four hours of driving.
Thankfully, shopping for glasses online makes this easier, especially with virtual try-ons. These are perfect for when you’re multitasking – packing, planning, and persuading your teen to actually put things in the suitcase.
How to pack smart for any road trip
Whether we’re on a road trip through Californian, or heading off to the Lake District for a weekend, the principle remains the same – pack items that will work whatever the weather does.
A lightweight scarf is great as a wrap for chilly evenings by the fire, but it equally works as a pillow or a handy thing to put your sandwiches on at the beach. Plan outfits based on your itinerary – one for warm days, one for cooler nights, and one slightly smarter option in case you end up somewhere unexpectedly fancy.
As an aside – I am a believer in rolling clothes, not folding. I’m a devotee of packing cubes that help keep us organised when we’re away from home and if they are the compressing style, that’s even better.
How do you build a colour that makes packing easier?
Honestly, this one’s easy. Stick to three or four base colours and keep them as neutral as possible. For me, that means black, white, beige and grey. If you’re more of a colours person, you can add pops of colour with bags, scarves, sunglasses etc.
How to blend style and function for the perfect road trip look
The perfect road trip wardrobe is a fine balance of ease, coordination, and just enough effort that you can arrive looking put together – and not as if you’ve just spent six hours in the back seat of the car.
In summary, then – breathable fabrics, a limited colour palette, accessories and the right glasses that make you feel confident and that let you see all the sights!
