Whenever you have to pack for a trip that's more than just overnight (or will involve a change of climate during the trip), you may face a challenge as to how much (and what) to pack.
Too often, guys will either bring the minimum and be caught unprepared for unusual weather or fashion requirements, or drag along their entire wardrobe and end up using a fraction of what they packed.
Here's how to get the most out of the minimum:
Pick a single color theme. Rather than going with a full palette of colors, go with one basic major color (like blue) and select all your other clothing to match that main color. That way, you won't be stuck with a bunch of unrelated clothing items that only go with a given outfit or clashing color.
Plan on dressing in layers. This is especially important if you're going from a warm to a cold climate in the same trip. You don't have to pack all your cold weather wear – just select items that will go together and will pack flat in your luggage. If you really need major cold weather coverage, a down-filled jacket beats a fleece for warmth and will collapse down to nearly nothing.
Be ready for dressing up and down. Even if you're doing a casual vacation, it will be good to have a dressy jacket and pair of pants for spontaneous events (like meeting a lovely lady you want to take to dinner). If you're traveling for business, be ready for some down time with 'knock around' clothes. Even if you're in a cold climate, you may end up in a hotel with a pool or a place with a hot tub. Pack a bathing suit!
Most importantly of all, get in the habit of thinking ahead to what you'll actually be doing, rather than trying to cover all possible scenarios. With experience, you'll learn what to leave out, and what you must never forget to bring.