I first stole something when I was a teenager. I was living between an abandoned building and my girlfriend's house and didn't really have money for food. I pocketed a Snickers bar from a gas station.
It was very calculated -Snickers has the most calories by weight. It was easier than I thought it would be. I made this a regular habit.
Later, I would start stealing those cup noodles from a supermarket to feed myself and the girl I ended up living with. We were broke. Had a rented room in a sharehouse that we split. I would later get a job at that same supermarket.
Eventually I moved in with a girl who had a little eBay shop where she was flipping second hand clothes. This was before etsy, depop, etc. She would go to the Goodwill (or any other thrift shop) and pick out things that were cute or had designer labels and sell them online.
We eventually decided to combine our skills. We would go to malls, she would talk to the lady at the counter and I would stuff things she wanted into my satchel. Lipsticks, stockings, anything I could fit in my bag.
Nothing is more invisible than a bored boyfriend in a mall.
We'd sell these little things on eBay and make quite a bit of money. Those lipsticks were close to $20 each. The stockings too. I could fit a few hundred dollars worth in my bag and we could do a few stores in a day.
Eventually we moved up to designer fashion. My girlfriend would dress very fancy and would be very chatty with the cashier.
She would even buy a dress that cost a few hundred -it didn't matter, we were going to sell it anyway. Meanwhile, I would stuff a few dresses in my satchel.
The security tags would beep on the way out, but we made a point of walking out together. I would keep walking and she would show her bag with the dress she just bought in it and act very confused.
Those security tags don't last long against a drill and a pair of pliers, just need to avoid the ink vials.
Our final and the best technique; I would go to Toys R Us and buy the largest lego set I could find. They'd cost a few hundred but came in a giant box.
We'd take the box to the car and empty all the lego out (I'd get to build that later). I'd keep the box in the trolley and push it around for the rest of the day.
We'd then go back into the malls and she'd do her “fancy lady buying fancy clothes” act. Meanwhile, I had a giant box that I could fill with basically everything I could fit.
Those boxes are huge and clothes compress really well. We'd beep on the way out, but no one really gave us much thought when I showed my giant lego box complete with receipt.
The most we ever stole in one day was about $5000 using this technique.
I stopped doing this once I got a real job that was paying well enough, since the risk wasn't quite worth the reward. I'll still steal things for fun sometimes though.