Sartorialee’s ‘How to pack for a holiday’

Below is a re-run of an article I recently collaborated with Oliver Sweeney on:

When it comes to deciding what to take on your holiday, as the old saying goes, less really is more. A successful (and stress-free) holiday can, more often than not, boil down to the clothes you take with you and how well you pack them. With bank holidays aplenty and the summer holidays coming up, we’ve outlined the rules to packing a discerning wardrobe, to ensure you have the best holiday you can, with some expert advice from experienced traveller and menswear specialist, Lee Osborne.

  1. Do not take everything

Perhaps it’s the British sensibility in us that makes us feel that we must be covered for all occasions when we’re on holiday. However, in reality, you’ve researched your itinerary and you’re well prepared, so why overcompensate (and over-weigh) your suitcase? “Tot up how many days you’re away for and work out what to wear as day and evening attire,” Lee advises. “When deciding on what to take, I always think practically and try to make outfits work two or three ways e.g. change up a navy blazer with an open-necked shirt. The space you save can be used to fit in new purchases you make whilst away.”

  1. Never underestimate accessories

Accessories are the key to making your outfits as versatile as possible whilst away. Whether it’s a travel document holder to ensure that you keep all of your most important assets together, or a dark leather belt to team with a pair of chinos come the evening, they’re the finishing touches (and saviours) to your holiday wardrobe. Lee also believes that hats are hugely underrated: “I love wearing a panama hat, especially if, like me, you’re follicly challenged.”

  1. Don’t roll, fold. 

Packing your case is often the most strenuous part of going away and if you can’t successfully fit everything into your suitcase, you risk damaging and over-creasing your outfits before you’ve even arrived. As an experienced traveller, Lee’s advice is to always fold your clothes. His tip for packing a blazer is one of the best we have heard: “Always fold blazers inside out and they will be virtually crease free at the other end of your journey. I always hold the blazer at the centre of its collar, flip one shoulder inside out (but not the entire sleeve.) I then fold the jacket in half backwards, so that the shoulder pads sit on top of each other, with the jacket lining facing outwards. Fold once more in, half horizontally, and pack.”

  1. If you can take just hand luggage, do it

“Unless I am going on a long haul flight, I find that taking hand luggage is far easier and there’s less chance of losing your possessions.” Lee’s advice when packing in a more limited space is also invaluable: “Start with heavier items in the bottom part of your hand luggage and frame the corners with shoes.” For keeping your shoes in shape, Lee also supports our Cobbler-in-Chief’s shoe care advice to keep underwear and socks in shoes to fill them out, as a shoe tree naturally would. The importance of a shoe tree, as we’re sure you are aware, are significant for not just maintaining the shape of your shoes but also for absorbing perspiration after a day’s wear.

  1. Follow your gut instinct when packing

“If you already doubting your decisions about what to pack then, chances are, you probably have packed too much.” Lee’s advice comes from experience and practice. With simple pre-planning, sensibility and careful consideration of our rules above, we’re sure you’re have a holiday (and the outfits for it) to remember.

Lee Osborne is an experienced traveller and menswear specialist. He runs the brilliant men’s style blog, Sartorialee: Dressing the global-trotting man. Find him on Twitter @sartorialee.