Step 1. Check the weather and the cultural expectations – this one is obvious, you want to know what type of clothes you'll need. Obviously you need more clothes for travel to colder destinations. Add jackets, tights, hats and boots as required. Its also useful to do a Google search and check whether your destination will be a place you can wear skimpier outfits or somewhere you should be covered up. There’s nothing worse than arriving somewhere and feeling like the unfortunate centre of attention. When in doubt, always take a few conservative pieces just in case and check out what the women are wearing when you arrive.
Step 2. Gather Your Basics - Without fail I always take the following things with me – breton style nautical top, black and white singlets/tees, khaki hooded cotton jacket, leather shorts, denim jeans, one LBD (black bodycon number usually works well) and a white silk collared shirt. As in every day life, good basics are the foundation of a versatile travel wardrobe.
Step 3. Add key colour items – choose a colour palette for a few additional pieces. This reduces the likelihood of having mismatched outfits. Depending on what I have in my wardrobe I usually add a maxi skirt (great for travelling), long sleeved shirt, a few mini skirts and a pair of shorts in my chosen colour palette. You can of course choose a couple of colours for your palette, just try to make sure they are all compatible.
Step 4. Rationalise your shoes - Shoes are the most bulky part of your luggage and if you can restrict the number of shoes you take with you, life will be much easier. But you don’t want to feel like you lack shoes either – I usually take one pair of classic black patent heels (maybe a second pair if I am going somewhere dressy like New York or Paris), a pair of ballet flats, ankle boots, a pair of comfortable shoes like converse or plimsols and a pair of gladiator sandals. Thats conservative and still 5+ pairs of shoes... eeep!
Step 5. Complete with Accessories - I usually take a few nice statement pieces of jewelry which I can throw on in the evening to feel a little bit more dressed up, such as a pair of tassel earrings or a gold coin necklace. My Asos floppy fedora always comes on holidays with me, I also almost always take a bag with a long shoulder strap so it can be worn cross body, so I can relax when wandering around busy train stations and streets.
Other tips?
Do a layout – when packing make sure to lay everything out on your bed so that you can visualize the outfits and how they will go together. This has been the one single factor that has helped me to create better holiday wardrobes.
Cosmetics and Beauty – I don’t own much make up and my beauty inventory usually consists of bronzer or blush, a good moisturizer and cleanser and maybe some mascara if I’m feeling adventurous. I do however often take my hair straightener for city breaks (but not beach breaks), knowing that most hotels will have a hair dryer.
Other key things to take? A good book (Man Booker prize winners usually ticks the right boxes), ear plugs and an eye mask, a notebook for writing down ideas/travel stories, a good camera, and a great attitude. Oh and finally, make sure to roll your clothes up tightly so all of the above can fit in your carry on.
Update: If you have trouble packing it may also be that your wardrobe is in disarray. Why not follow my 7 Steps for Wardrobe Rehab here to make packing (and generally getting dressed) easier?