What it is: Everlane Weekender bag, $95
Why we like it: Equal parts rugged and robust, this canvas beauty with leather details can stand up to whatever debaucheries those bachelor party weekends can throw at it. The handles are short enough to hang at your side and long enough to sling over your shoulder, eliminating that cross-body strap and any chance of someone calling it a "man purse." Best part? Everlane makes and sells the bags themselves, so you save money that can now go straight to your vacation beer fund—or daiquiri fund, depending on your destination.
Where to get it: everlane.com