Plan outfits around the days
Start with what you expect to do: travel, walking, dinner and perhaps time outdoors. Lay out complete outfits and look for pieces that can do more than one job. You do not need a new combination for every photograph. Choose a small colour palette so layers work together without much thought.
Make shoes earn their space
Wear a comfortable pair for the journey and consider whether you genuinely need another. If your plans call for a different style, choose a pair you have already worn. A short break is a poor time to discover that new shoes are uncomfortable after a long walk.
Pack for the forecast, with one fallback
Check the forecast close to departure and adjust your layers. A light outer layer can be more useful than several bulky alternatives. Keep any items you will need during the journey within reach, so you do not have to unpack the whole bag at a station or airport.
Keep essentials together
Make a short checklist for your identification, booking details, phone charger and any personal essentials. Keep them in a consistent pocket or pouch. Save the address of your accommodation and arrival instructions somewhere you can access easily. Check the baggage allowance and item restrictions for your actual transport provider before leaving.
Do a final edit
Close the bag, carry it around for a moment, then remove the things you packed only because there was room. Leave a little space for the return journey. The goal is not the smallest possible bag; it is a manageable bag containing the things that make your own trip comfortable.