Maximize your bag space
The size of your bag will depend on how long you're traveling for. A medium-sized backpack does the job if you're only away for a few days, but week-long breaks usually require a carryall or suitcase.
Ideally your bag will have several compartments for dividing up your stuff. Many backpacks come with a laptop sleeve, which you don't necessarily have to use as intended — they're great for neatly piling up folded tees and button-up shirts, freeing up the rest of your bag for more bulky apparel.
Wear your shoes
Speaking of bulky, shoes tend to dominate in the battle for baggage room. Boots are super versatile, but trying to fit a pair in your backpack or suitcase with the rest of your things will be like trying to get The Incredible Hulk into a wetsuit. For that reason, they're best stored on your feet as you travel.
Light sneakers or plimsolls will serve you well as comfortable, city-roaming kicks, without hogging too much space, while flip-flops take up next to no room when slotted neatly at the bottom of your bag.
Even if wherever you are isn't experiencing the erratic weather we are this year, planning outfits in layers to remain adaptable is still a shrewd move. T-shirts and tanks are the foundation of good layering — bring one for each day you're away and build up with casual shirts, a cozy sweater or hoodie and a foldable raincoat for when the weather turns soggy.
A more dapper shirt is nice to have for fancy outings — choose one that you know stays sharp without an iron and pair it with some light chinos. While we're on bottoms, you'll want some comfy jeans for those low-key days and evenings. Pick out your favorite pair and travel in them to save valuable packing space.
Accessorizing on the go is all about hats and sunglasses (great for hiding messy manes and hungover eyes, respectively). Snapbacks help to fend off sunstroke while beanies are good for cloudy day exploring, and you can't go wrong with Wayfarer-style shades. Alternatively, stay classy in Aviators or Clubmaster-style specs. Keep these accessories in your day bag for easy access.
Embrace on-the-go grooming
Disguising yourself on sloppy days is acceptable, but you can't spend the whole trip hidden away. Investing in a quality haircut a couple of weeks before traveling allows you time to get accustomed with the inevitably unpredictable first few days of styling. Also practice streamlining your grooming regime with as few products as possible — you don't want to spend your holiday in front of a mirror. Oh, and embrace the facial fuzz, if you can pull it off. Vacation beards are the best kind of beards.
ASOS Stylist James Welsh for these pics — check out more tips, tricks and inspiration on his Instagram.