Any suggestions for $100 or less?
I don't think it qualifies as stylish, but after ruining one too many rollaway bags on frequent consulting travels, I've had a Victorinox bag for two years, and it still looks like new. It has an integrated garment bag, plus a ton of space for other stuff. Convenient front pockets for papers, toiletries, etc...
This suitcase is very well designed and like all tibuk2 products it takes a beating and still looks good. It has a lot of compartments for your toiletries and even a space for shoes.
http://www.timbuk2.com/tb2/products/travel/checkpoint#product=6-30238
For $100 or less browse the net for something you like and watch the discount sites (froogle, ebay, craigslist) for it. Also, outlet malls often have really good deals on luggage.
It's worth it to wait until you find something you like. The best thing, luggage tends to go on sale frequently.
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I use Briggs & Riley's baseline series (specifically the 20 Carry-on) which is great. It is durable, lightweight and coupled with the OneBag packing can carry a lot.
If you need more room they have the expandable version as well. If you are looking for something with wheels I wouldn't suggest a duffel since they not as durable and tend to get thrown around being more a bag than a suitcase.
Also, Briggs & Riley's warranty and repair is second to none. They do almost all repairs for free including damage done by airlines when they force you to gate-check your bag.