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Packing Large Luggage- Bad Idea?

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I am going on a 4 month trip, the first 3 months are business and the last month is pleasure. I will be taking a greyhound to Canada, then plane to London, then probably Eurail around for about a month. I'll probably stay in a few hostels as well as hotels. I will need my work equipment (laptop, etc) and I will need a couple cocktail dresses and shoes to match, as well as my work clothes and travel/weekend clothes.

So, my question is: is it a bad idea for me to pack my enormous Delsey Duffel? I know it will fit everything and I will only need a purse for carry-on, but... taking a bus, eurail, staying in hostels... is packing a large bag like that an invite for thieves and trouble/complicatons? If so, does anyone have a recommendation for luggage?

Thanks!

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