I just recently got the Western Flyer and am looking to put it through some paces. Right now, I've already fit everything I used to fit in my small roller AND have room to spare. I'm quite surprised. This is a business trip and I mildly overpacked, and definitely could have pushed it further.
Everything you read below fit in the Western Flyer and pretty much left one of the half-compartments empty except for my toiletries. LOTS of spare room. I would also like to mention I am about 5'10" 245 lbs (shoe size 9.5), so I'm not an especially small man... lots of extra large clothes and a waistline that hasn't been below 40 for a while.
1 - Western Flyer
1 - Mini Clear Organizer Pouch
1 - Small Clear Organizer Pouch
1 - Medium Organizer Pouch
1 - 3D Clear Organizer Cube with Key Strap
1 - Absolute Strap
2 - Small Western Flyer Packing Cubes
1 - Large Western Flyer Packing Cube
1 - Horizontal Freudian Slip
3 - pairs of wool socks
3 - pairs of Ex Officio Give n Go underwear
1 - IceBreaker 200
2 - Grey polyester sport tees
1 - Khaki pants
1 - Brown Corduroy Pants
1 - Khaki Cargo Pants
1 - Dress shirt
2 - Ex Officio long-sleeve shirts
1 - thin, long sleeve, v-neck sweatshirt
1 - leather belt
1 - blue canvas belt
1 - pair swimming trunks (always an optimist)
1 - pair Vibram Five Fingers
1 - Suede Wingtips
1 - sleepwear bottoms
1 - Ex Officio Storm Logic Jacket
1 - disposable razor
1 - shaving brush
1 - tube of shaving soap
1 - bottle conditioner
1 - bottle shampoo
1 - travel toothbrush
1 - travel toothpaste
1 - deodorant
6 - alcohol pads
1 - 13" laptop
1 - 13" laptop power supply (with stupidly large rectangular brick)
4 - Assorted electronics cords (USB cords, serial cables, etc)
4 - Assorted little things (USB thumb drives, dongles, small electronics jumpers, etc)
1 - pen
1 - pencil
1 - sharpie
1 - pad post-its
1 - mini stapler
1 - manila folder with 6 pages
1 - Volant moleskine
1 - iphone
1 - 98 page Quarto sized hardcover book (9.5 x 12)
1 - A4 size notebook
1 - Accell Travel Surge Protector
1 - 20oz Kleen Kanteen Stainless Steel reusable water bottle
1 - Passport
1 - set of keys
1 - wallet with the usual stuff
1 - Blu Samba Jr. phone
1 - Escort Redline radar detector
1 - USB Car Lighter Adapter
1 - Nexus 7 Tablet
First off, I do wash the underwear and Ex Officio shirts after I wear them. I also know I am somewhat overpacked for a 3-day trip, but I wanted to see what I could pack into it so I could have a "standard" packing list.
I will be wearing one pair of shoes, socks, pants, underwear, undershirt, 1 Ex Officio shirt and the jacket. I will be carrying the tablet, phones and keys until I get to the airport, then the keys will be put in the small pouch or small front pocket. As it turned out, I still have one empty Small Packing Cube and an empty medium Organizer pouch.
The water bottle is in the water bottle holder. Oddly enough, I was never one to carry water around, but this bag got me thinking about it.
In one small packing cube, I packed socks, underwear, undershirts, grey v-neck sweatshirt, swimming trunks, Vibram Five Fingers and blue canvas belt. This cube is placed in one of the half-compartments. The items in this cube are rolled.
In the large packing cube, I packed the dress shirt, long sleeve shirts, pants, sleepwear. This is placed in the large compartment.
In the Horizontal Freudian Slip, pretty much all of miscellaneous and work-related items fit, except for the laptop. This is placed in the large compartment between the center of the Western Flyer and the large packing cube.
The laptop, I am placing between the large packing cube and the Freudian Slip.
In the small organizer pouch, I put that on the O-ring in the smallest front pocket and it contains my passport and copy of itinerary. I am planning on using this pouch as a sort of catch-all for things important things I want to be able to access quickly, but infrequently (passport, frequent flyer cards, copies of itinerary, etc)
In the mini organizer pouch, I placed my miscellaneous small electronics (USB drives, dongles, etc). This is attached to an O-ring in the large compartment.
The 3D Organizer cube contains my toiletries and has a keystrap attached. I've attached this keystrap to the O-ring in the empty half-compartment (opposite of the small packing cube). My plan is when I get in security, to unzip and remove the toiletries and leave them on the belt.
So, in a pocket by pocket description...
Small pocket in front contains mini pouch attached by small key strap and radar detector. I planned to use this to hold my travel receipts, but that might be the medium pouch now.
Larger pocket in holds the car adapter and 3D organizer cube with keystrap.
Water bottle pocket holds a water bottle.
1 of the split compartments holds the small packing cube.
The other split compartment is EMPTY... well, it has the medium organizer pouch, but that's empty too! I could put my tablet here, but I honestly like carrying it in my back pants pocket.
The large compartment holds a large packing cube, laptop, horizontal Freudian Slip and mini organizer pouch.
The backpack strap pocket just has backpack straps, though I could see it holding manila folders or other folio sized items in a pinch.
With everything I've packed, I feel absolutely comfortable doing a 5 day trip (or even longer, depending on circumstances). On my next longer trip, I will experiment with packing slightly dressier, with an extra pair of shoes and/or a sports jacket.