Every Christmas Mrs. Wheelz and I fill a stocking for each other; about a dozen little trinkets or candies or fun silly things. Nothing that costs more than a couple bucks, usually.
The trouble is that we’ve been doing this for so many years it’s getting a little stale. I always end up looking in the same aisles in the same stores year after year and a certain sameness has set in that I want to break out of this time.
So, what do you suggest I put in there?
So, when I saw this it was right on top of “Have you ever used your sock to masturbate?”
Not exactly what I had in mind, though.
One of my favorite stocking presents was a spool of twist-tie material that could be cut to any desired length. ANY DESIRED LENGTH, DO YOU HEAR ME? Heck I just used it yesterday.
I’m not against practical stuff – how about travel sized advil or toothpaste or deodorant, if she usually carries those things in her purse or gym bag. Her favorite lipstick, if she wears it regularly.
Everyone likes stickers. 
Does she have any hobbies?
Since I don’t know your wife, here are some suggestions of things I would like to see in my stocking this year.
Single serving bottles of liquor are a stocking staple in my family. We like the Burt’s Bees variety packs too.
[ul]
[li]Nicely scented lotion from Bath & Body Works, et al[/li][li]Tickets to a concert (okay, maybe not if you only spend a few bucks)[/li][li]A music box that plays the Lexus theme music (no, seriously, don’t get this)[/li][li]Chocolate covered almonds or Ghiardelli squares[/li][li]OPI nail polish[/li][li]Nail file[/li][li]iTunes gift card[/li][li]Fun earrings[/li][li]A crystal ornament[/li][/ul]
Little bottles of hand sanitizer from bath and body works. They’re a little too expensive for what you get volume-wise, but you can get a bunch of different scents. And it’s a practical item.
Travel-size toiletries are a current staple, one of the things I’d like to change up. Good idea though.
She doesn’t wear lipstick enough for me to know her “favorite,” and I wouldn’t dare trying to pick out that or any other makeup for her.
Hobbies? She loves to draw. I always include colored pencils or markers or glittery gel pens. That’s one I’ll keep doing.
Good ones!
Oooh, she loves Burt’s Bees! Thanks.
Single-serving liquor? Too small. 
World Market/Cost Plus has tons of sample-sized fancy foods, candies, trinkets, etc. That’s where i get stocking stuffers.
A magazine she likes but doesn’t subscribe to.
A photo copied from an original she doesn’t have that a parent or sibling has
Something you’ve made - a simple craft like map magnets
So much good stuff from these folks: Archie McPhee Wholesale - Accoutrements Toys and Novelties
I can vouch for the Ballpark gum being delightfully awful.
ETA - I buy them through Amazon
A handmade card or written note. Something sweet, like all the things you love about her (especially love about her this time of year).
It will get you laid, I promise.
Warm fuzzy socks… who doesn’t like warm fuzzy socks.
An orange at the toe, naturally!
How about a silly ring from the gumball machine?
A kneaded eraser and a brass bullet pencil sharpener?
Some things I’ve gotten and enjoyed:
These Shower tab things. I liked them enough to ask my sister where she got them - it was Whole Foods (mine were lavender).
Tea bags
Tea Tree Oil foot spray (refreshing after a day standing and walking)
Festive/fancy purse packs of tissues. (Often near the registers in card stores)
emery boards
I like things from the toy store such as finger traps and little brain teaser puzzles.
I like that you do this. I tried to get it going as a tradition in our house but it never really caught on with my husband. He grew up in a family of smokers and his stocking go-to gifts are cigarettes, lighters, and scratch-off lottery tickets.
My sister and I handle stockings for each other now.
Get a magnetic sheet from a craft store and glue some of her favorite pictures (wedding, beach, vacation, pets, kids, grandkids, etc) onto in. Trim around them and make refrigerator magnets out of them.
Pink duct tape. Everyone needs duct tape.
Things that are constantly getting lost. Around our house, that’s fingernail and toenail clippers. If she does her own nails, emery boards and an orange stick or two. Clear polish, which is good for many things.
Things that are whimsical. Kid’s bottle of bubble soap with wand. Mini LED flashlight. Mouse nose. Whacky pot holders.
(I see I was too slow with the emery boards. Does she run out of glue or AA batteries?)
Maybe a little sketchpad? I know they sometimes run a little high in price. Does she like to doodle, or like sticky notes? Those are always useful for keeping track of drawing ideas and other things.
Does she outline her drawings in pen or anything like that? I know I love certain types of pens for mine, before coloring.
What about gift cards for her favorite clothing stores?
Does she have a passion for a certain activity (maybe drawing might be one) that inspires cute jewelry ideas, like rings, necklaces or earrings? For instance, this is one of my favorite necklaces ever, as a pianist.
One year I got a cup and ball toy similar to the one here in the first picture. We all had fun Christmas morning playing with it, and throughout the day. Seriously, it’s been 4 or 5 years since and I still pick it up and play with it a bit just for fun.