I think it's totally natural to feel torn when it comes to your approach to packing. Part of you wants to go balls to the walls crazy bringing the cutest, trendiest shit you own and the other portion just wants to keep it simple. Trust me, this is a dilemma I face 24/7.
The underlying factor is that we're stimulated by so much content (oops, blogs like this included) that inspire us with all these "what-ifs" and "that could be me" ideas, so when it comes down to picking what to pack, it's impossible to make choices. So, here's some ideas on how to channel the impossible to make the best damn good-looking choices to packing.
1. First, let go of the idea that you can be repping a million different styles and trends. In a perfect world our closet would travel with us, but lets be real - that ain't the case. So no, you can't be the sporty menswear chic, glamour diva, bohemian hippie, and girl next door all in one take.
2. Choose two inspirations to base your packing choices off of. It'll still leave room for creativity but limits the "what-ifs" we tend to have. Inspirations can be based on ideas like trends, weather seasons, or looks. Whatever it is, narrow it down. BONUS! Maybe you can narrow down your closet in general. It'll help you next time.
3. Physically take out some choices to visualize. Don't be afraid to start big and cut down. No one said you can't lay out all your favorite tees, pants and jackets to start with. God knows we've had a shit ton of stuff sprawled out on our bed before. Just know you'll start putting back one thing after another till you've found the chosen ones.
4. If you can only wear it once, don't bother. Force yourself to think of at least 2-3 possibilities of use before even considering it a place in your suitcase.
5. Your closet will be there when you get back. Not packing something this one time doesn't mean it will no longer exist for future use. Another point to letting go of wanting to bring every cute thing you own.
6. Plan around versatile pieces, not outfits. Let yourself get creative while on your trip to put things together. When you pre-plan outfits, you restrict yourself from getting inspiration while traveling. Let the city or culture inspire you.
7. Lastly - you know you have to bring versatile pieces but what the heck are versatile pieces? To be honest it is different for everyone and each person's "style", but lucky for you, you've found this project and are well on your way to figuring your shit out. (At least I hope.)
So, take each experience as a learning opportunity. Practice makes perfect. 2015 can be filled with packing opportunities. Just start planning those trips.
Happy holidays, happy planning and happy packing.