My son also uses a waist pack sometimes! Very handy to carry a few extra items (in addition to keys, phone) like a small hand sanitizer or sunscreen.
Regarding holiday shopping, my son has been stalking the
LEGO website trying to score the Delorean from Back to the Future. He was finally able to place an order with a future shipping date. He is asking for that for Christmas, so “my shopping” has officially started lol.
I think it took me 6 posts before I Googled “Bonne Maman advent calendar.” The person I think would like it the most, is me! How do you work Advent calendars into your gift giving since they have to be given before the holiday. I’m thinking in the family I open presents with on Christmas morning this wouldn’t count as a present. Re: fanny packs - my 3 early 20s sons laugh hysterically at my husband wearing a fanny pack (that he acquired in the 1980s) because he likes the convenience. I didn’t realize that some members of the younger generation wear them.
I’ve got no ideas for holiday shopping except that I’m trying to figure out how/if to inform extended family that I don’t want to give them gifts this year - everyone has lots of stuff, can afford their own stuff, are in the downsizing phase of life, and I feel don’t like (probably donate) the things I give them.
I have a daughter with a mid November bday so I gift her advent calendar then. But otherwise there is no law that it needs to be a December advent - I would give as a gift and encourage it to be a JANUARY calendar! Or just winter! Or no date at all!
Guess you do it like my aunt did one year (which hurt my dad but he wasn’t doing the shopping)-- " I think we shouldn’t exchange gifts anymore." Husband’s sister finally brought it up one year and personally it was a relief.
“I think we should not exchange gifts anymore.”
We did this years ago. My family was fine, H’s sisters and mom were upset. But they got over it. Honestly having to buy, wrap and ship so many gifts ruined Christmas for me. They can do what they want (and they do), but I had to do this for me.
I do recommend that you tell them ASAP. Don’t wait until mid-November when they have already bought stuff for you and your family. Also tell them that they are free to continue whatever they want but that YOU are bowing out.
We have been doing this in stages. We have leaned heavily on pictures, especially for the oldest generation, who have digital frames that get updated with the newest picture static for a while, before switching it back to random (we do that remotely for them). I do a lot of digital advent cards for in-between family & friends (I like the Jacquie Lawson ones!).
With the two siblings on one side we agreed that we would give each other our favorite “wine find” of the year- a wine that we enjoyed, thought was good value and was something you could drink on a normal night, and ‘gifts’ only for the little kids. With the siblings on the other side we agreed on gift cards for the kids (all HS & college age), and a (specifically inexpensive and ideally either digital or consumable) ‘memento’ between the siblings. Memento has turned out to be very fun! Some examples: a brother found an old picture of all of us as kids, had it cleaned up & sent to us digitally; another brother found a digital version of an old record that was a part of our shared childhood; a third brother found a forgotten candy.
With our own kids we have been doing a family trip as our main ‘present’ for many years now 
The key thing for us is the moment of connection, the touch point of closeness.
We moved to gifting to just the kids years ago. Of course most of the “kids” are now adults so we’ll probably transition again when that generations starts having their own babies.
As nieces/nephews age, here are some ways used to transition that I’ve heard…
Not saying any of these are right for OP and other posters. Just putting some ideas out there.
Gifting to family depends on how big your family actually is. We’ll always send gifts to one aunt because she is all we have left on that side of the family. Not all gifts are tit for tat.
We gave that up years ago too - it was the worst part of Christmas for me - trying to think of gifts for people who seemed to have everything. We started by eliminating gifts for adults, but still buying for young kids. Once the kids got older, we stopped them too because we were mostly just exchanging store gift cards 
My husband insisted we keep gift-giving with his parents, but last Christmas they gave us nothing, so I put my foot down and said enough. That was another case of just exchanging restaurant gift cards with one another.
My son-in-law’s family is big on the gift-giving, but they draw names and have a set dollar amount. My daughter always requests that her “gift” be a donation to her favorite charity.
As adults, we weaned ourselves - haha. We started doing a pick (us siblings, our parents, and grandparents). So just one gift to buy. And eventually the siblings’ kids had their “cousins” pick which we found worked really well - they all concentrated on “giving”. Finding a perfect gift, wrap it up, etc. I think they liked the giving more than getting!
Then we moved to the adults adopting a family or two or some other charity. The women went out shopping together for an afternoon. My dad would help wrap and provide snacks. A brother delivered the gifts.
I’ve weened my family a few years now, I just can’t stand buying a lot stuff, so I only give edible items now and stocks in their stockings, lol, and I’m requesting stuff that I actually use, not some random gift somewhere.
My kids make it easy - they send me a list with links to what they want, with sizes/colors and I just have to click away and Wala! Christmas is handled! 
My husband, on the other hand, is difficult - he always says he doesn’t need anything 
My H too. I hate shopping for him!
I tried to talk to my siblings, etc about stopping the gifting and it was as if I had suggested killing someone. So I transitioned first to just a gift for each household, and now just a gift for my folks. Some people follow suit, some do not, that’s their choice.
It is hard on my mom though, because as long as we officially are still gifting, she wants to give everyone something in addition to the generous money gifts. Guess who does her shopping and wrapping?
I still do a fair bit of shopping for my kids and their SO. But they make lists and so it’s not like I’m starting from scratch. I wouldn’t mind reducing to less gifts, more substantial gifts but they still seem to love getting a needed item of clothing or a kitchen small appliance or a pair of earrings!
H and I haven’t really exchanged gifts for years. I’ll have a thing or two wrapped for him - something like a jacket or sweatshirt from our MetroParks.
Family wise, for my two sibs I do usually see at the holidays we do a Secret Santa. We each draw one name, there is a gift theme - usually something food/cooking related - and the $ limit is around $25. So it’s really just a fun part of the day we celebrate Christmas and we have a whole routine around opening, guessing, etc. Kids receive stand alone family gifts until they graduate college - which now only includes 2 kids between 3 siblings!
And I do stockings for my 3 kids and at least one daughter in law.
Oof! That was the set up with my parents too. Double the work for me. Bah humbug ; )
My parents did that too when the kids were younger (up through high school). Basically, H & I would buy the kids a lot of things over the summer through Xmas and I’d keep a list. Sometime in December I would sort it out what would come from Santa, us, and my mom and then wrap accordingly - and of course, making sure the kids got approximately the same $$$ of presents.
I mentioned earlier that H used to insist on buying stuff for everyone. His family was the same way. My side of the family was easier, especially when it got to the point where I’d hand my sister’s kids gift cards and my sister would hand me gift cards for mine. Really? What’s the point, lol. My niece and nephew on H’s side, he kept insisting they needed gifts in their mid to late 20s. I pointed out - don’t you think it’s weird when your aunt send us things? Yeah. See?! So we cut that off. We still buy our parents stuff - usually just food baskets now. And he buys one great-nephew stuff, because that nephew is more like a friend vs family. And I’ve also put my foot down on co-workers! Really… he would insist on buying trinkets for 5-10 co-workers and MINE too! UGH! Now, it’s just some candy for the secretaries. And at least the kids out-grew having to buy stuff for teachers… It never ended… I love Xmas for MY little family, not everyone.
The other funny issue was that when we used to exchange gifts with H’s family and my SIL/BIL were still working, their income was almost 10x what ours was. So, we would be gifting my in-laws and book and a sweater, and they would give them a super giant TV screen and a brand new computer! One year, they paid for a painter to repaint their entire house… Everyone tried to be nice about it as best they could, but still. really? Hmmm… what would you be more excited about, lol…
If we celebrated Christmas I’d be ALL over advent calendars. I love love love the idea. I still do 8 gifts for Hanukkah for my mid 20’s daughters. I have their big gift, diamond earrings. And two,p other nights that combine a product with a gift certificate (Wirecutter recommended nail clippers and nail salon GC. AND Lolavie hair products and hair salon GC)Still working on the other 5.
I’m surprised no one has come up with a Hanukkah 8-gift surprise box. Beauty products wold work… or of course sweets! 