Here I sit in a hotel room in Milwaukee, Wisconsin. Our team is presenting to a company up here tomorrow and heading back to Indianapolis. I bought a new suit for the trip – it was on sale for about 70% off and I couldn't pass it up. It's chocolate brown – almost black – and quite comfortable. I haven't bought a suit in quite a few years so I treated myself to an entire outfit – including slip-on shoes.
In fact, I had my entire trip in a Messenger Bag – change of clothes, laptop, magazine, etc. I wore the slip on dress shoes with my jeans so I looked like a nice traveler – it was really just to save space. And – they're slip-on so I can make it through security quicker. The Case Logic Messenger Bag I have has a padded rear compartment that my MacBookPro fits in perfectly, so I need not disturb my packing to access the laptop!
When I lived in Denver, I watched a morning show where a guy showed how to roll up a suit so that it's wrinkle-free. Folks usually bring a big garment bag or fold it up. The problem is that the garment bag gets folded, and folding it up causes wrinkles. If you roll up the suit correctly, you wind up with no wrinkles at all and you can fit it in almost anything.
I'm a big guy – so you can imagine how much space a suit should take up with me.
Roll Up Your Pants
To roll up your pants, be sure that the pants are laid out with the pants on their side and the creases lined up so the pants are perfectly flat. Starting at the waist, roll the pants neatly until they're in a nice roll. Lay them in your bag or luggage in a soft corner where they won't get scrunched.
Roll Up Your Jacket
Rolling up your jacket takes a little more finesse. You'll want to gently bend, not fold :), your jacket so you bring the shoulders back to touch themselves. This way, any fold occurs directly in the middle of the back and looks natural. Gently place the sleeves diagonally down one side of the jacket. You don't want to fold them as much as bend them. The end of the sleeve should wind up below the bottom button on the jacket.
Starting at the shoulder, roll the jacket up – but be sure that you don't wrinkle it as you go. It should form a thicker roll than your pants, but will keep well in the travel! Don't shove things into the bag around it, just lay it in there with socks, undershirt, etc. on top.
Unpacking Your Suit
As soon as you get to your destination, be sure to unpack the bag, unroll the suit, and hang it up. You should find it in perfect condition! Sorry I don't have pictures to match – I'm actually on the road so a cell phone camera just doesn't cut it.
NOTE: I don't seem to have as much luck with dress shirts – I usually wind up ironing them at the hotel.