Travelling with a carry on - for a trip that is two weeks or longer - can sound daunting. However it's the only way I travel now...and I travel alot.

One packing hack  - Wear a colour theme.
I might choose to wear navy/white/grey. Another trip I might wear beige/carmel/chocolate. Using a colour theme helps me to simplify and provides maximum versatility and flexibility with my clothing pieces. 

Another packing hack - Vacuum sealed bags with a handheld vacuum pump. Consider this if you are travelling to different climates and need clothing to suit each. 

Here is a general guideline to consider for a two week trip. This list can be used generally for men and women. Remember you can always send clothing to be laundered or find a laundromat nearby.  And....you can always shop locally if you need it!
  • Tops and shirts: 4-5
  • T-shirts: 3-4 (long or short)
  • Blouses: 2-3 (for women)/Shirts: 2-3 (for men)
  • Dresses or skirts: 1-2 (for women)/Sport Jacket: 1 for MenShorts: 2-3
  • Pants or trousers: 2-3
  • Jeans and or leggings: 1-2
  • Light sweater or cardigan: 1
  • Swimwear: 1-2
  • Undergarments: Pack enough for the duration of the trip
  • Sleepwear: 1
  • Socks: 4-5 pairs
  • Accessories - Hat/cap, sunglasses, scarf or shawl, belt(s)
  • Toileteries - Travel sized shampoo, conditioner, toothbrush and toothpaste, deodorant, razor, skin care, sunscreen
  • Electronics - Mobile phone, chargers for ALL of your devices, travel adaptors, power bank (you would be amazed how quickly one's phone battery discharges when taking photos and video)
  • Travel documents (passport etc and leave a copy at home with somone you trust)
  • Money and credit cards (I usually get funds from a local ATM as soon as I land)
  • Reusable water bottle
  • Small backpack
  • Travel sized umbrella (for sun and rain)
  • First aid kit (bandages, polysporin, liquid bandage)
For footwear, bring one pair of comfortable walking shoes, one pair of sandals or flip-flops, and one pair of dress shoes (if needed). Wear your heaviest shoes on the plane.

If you are travelling to a colder climate, you could wear your heaviest pieces of clothing to travel in. I am very sensitive to heat so even if travelling to colder climates I always dress in very light clothing while travelling on the plane. 
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Remember, the key is to pack versatile pieces that can be mixed and matched to create different outfits. Opt for light and midweight clothing and layer. 

Travel well!