I'm going to write about tipping without a single number in it, on purpose. The amounts are yours. The customs are what I can tell you. Tips customarily go to the people who are paid by someone else for your day: the catering staff and bartenders, the drivers, the hair and makeup team, the delivery and setup crews, the musicians in a band, an assistant or a second shooter.
The people who own the business (the photographer whose name is on the studio, the DJ who is the company, the planner who is the company) are traditionally not tipped, plenty of couples tip them anyway, and nobody who is good at this will ever ask. Read every contract first, because a gratuity or a service charge may already be in it. Then the envelopes get labeled the week of, one person hands them over, and it happens at the end of the night, or at delivery for a crew that leaves early.
The custom, plainly
Think of it the way you'd think of any night out. The person who owns the restaurant is not tipped; the server is. At a wedding, the servers are the catering staff, the bartenders, the drivers, the stylists, the crews who carry things, and the band members paid by the bandleader. The owners are the photographer, the DJ, the planner, the florist, and the baker, when they're the ones you signed with.
Tipping an owner is a gift, and it's received as one. Not tipping an owner is normal, and no one is keeping score. Two more that come up: an officiant from a house of worship usually gets a donation to the house, not a tip to the person, and a friend who officiated gets a gift and a thank-you, not an envelope. And the wedding party gets gifts. Never tips.
Read the contract first
Before any envelope gets a name, read what you already signed. A caterer or venue contract often carries a service charge, and a service charge is not always the same thing as a tip to the staff; ask the venue directly where it goes. Some contracts include a gratuity line outright; some leave it to you. The answer to that one question decides whether the catering envelope exists at all. Do the same read on the transportation contract and the hair and makeup booking.
Who hands it over, and when
Not the two of you. On the day you should have no phone and no envelopes. One person carries the bag: your coordinator, a parent, or a friend who takes it seriously, named on the Team Sheet. The timing follows the person being thanked.
The hair and makeup team in the morning when they finish. Delivery and setup crews when they leave, which is often before you ever arrive. The drivers on the last run. The catering staff and bartenders at the end of the night, usually through the captain to share, and ask the captain how they'd like it done. The band through the bandleader, one envelope or one each, whichever they tell you.
And a word from the booth: nobody on a mic wants an envelope handed to them on the dance floor mid-song. Catch us at load-out, or the next day, or in the mail with a note. The envelope list on the Week-Of Checklist is exactly this: who, from whom, when, and the amounts never print.
The other currency
In twenty years, the things I've kept are the notes. A review that names the person and the moment (the anniversary dance, the grandmother who wouldn't sit down) does more for a small business than any envelope, because it's what the next couple reads. A referral does the same.
A thank-you card with a photo from the night, a few of the photos sent to the providers who were in them (they'll want to show their work), and a hot meal at the right hour (Vendor Meals) are the thank-yous that last. Your providers will remember how they were treated long after they've forgotten what was in the envelope.
What usually goes wrong here
The venue staff tipped twice, once through the service charge and once in an envelope. A driver tipped nothing because everyone assumed the company handled it. An envelope with no name, in a bag nobody was told about. All of it comes from skipping the contract read and the list.
Questions I get asked
Is a tip expected?
Expected by the staff who are customarily tipped, welcome from everyone else, and demanded by no one you should have hired.
Cash or something else?
Cash in a labeled envelope is the custom, because it can be handed over on the day by someone who isn't you. Anything else can follow in the mail.
What if we can't tip everyone?
Tip the staff who are customarily tipped first, thank the owners in writing, and write the reviews. That's a complete answer, and no good provider will think less of you for it.
Decide it the week before, write it down, hand the bag to one person, and then forget about it, which is the whole idea. The thank-you that matters most is the one you write a week later, when you've seen the photos and remembered who did what.
Thanks! Chuck