How to Dress for a Stag Party. The fun of a bachelor party is you never quite know what's in store for the evening. Even if you have "plans," you never quite have plans. Throw in alcohol, a few ladies, and the last night of freedom and it can get quite interesting. Here are a few tips on how to dress for a bachelor party.
Find out where you're going. The night is going to start somewhere. So figure out what kind of establishment you'll be attending. Dressing for a nice steak dinner at an upscale restaurant is a lot of different to going to a ball game with the guys. Once you figure out the first stop, dress appropriately.
Bring options. If you are driving (and be sure whoever is driving is not drinking), pack some extra clothes in a duffle bag and toss it in the trunk. This way if the night takes an interesting turn and you go from brandy bar to sports bar you can "slip into something more comfortable."
Take extra underwear and socks. Okay, so you think it might be a tad embarrassing to bring an extra set of clothes and that the rest of the bachelor party is going to make fun of you and wonder why you're so worried about how to dress. Then, at the very least, take Mom's advice and bring extra underwear and socks. Bachelor parties have no time limit on them. You don't want to be hanging around in the same underwear for two and a half days until you finally roll home.
Be comfortable. This is the most important thing, however you decide to dress for a bachelor party. No matter what the evening's festivities, wear something that breathes, looks presentable, that's not too tight, and that you can envision yourself wearing for the next twelve hours. The bachelor party is not the night to break in a new pair of dress shoes!