I took an amazing class in high school (jfc, a decade ago) that taught me most of what I know, but I’ve picked up a few skills since then.  I hope they can be helpful for you in your shopping endeavors.

1. Comparison shop.
   Is there more than one grocery store in your area?  Do you have a free afternoon or if not, are you really good at journaling?  You’d be surprised the price differences between stores.  My hometown had a Grocery Outlet, a Fred Meyer, a Safeway, a Super Walmart, and a Winco.  If you shop at one every 2-3 weeks, keep track of your receipts.  Column up a piece of paper for your most-bought items, and go from there.
2. Discounted Food
   Most grocery stores have a shelf or rack in the far back corner that has everything from dented cans to seasonal items to day-old bread from the bakery, in addition to discontinued foods.  Take advantage.  There’s usually nothing wrong with these foods outside of them being cosmetically damaged.  I think my favorite discounted bin tale was right after Valentine’s Day when I scored six boxes of heart-shaped Junior Mints for maybe $3 total.  That’s typically the cost of one box of Junior Mints.
3. Very Ripe Produce.
   Best examples would be the single bananas you often find, already cut from the bunch and freckling.  These are best for eat-that-days, but you can also cut everything you find into pieces and freeze for smoothies, or cook down into freezer jam, or dehydrated.  I love super-ripe and cheap bananas, because not only can I make 2-egg-1-banana pancakes, I can also make banana-chocolate muffins (these are essentially vegan!) and banoffee pie.
4. Bulk-buy
   Sales are your friend.  Keep an eye out for buy-one-get-ones, for coupons, for larger options of your favorite foods.  Maybe your favorite potato chips are expensive in comparison to the store knock-off brand, but when it’s BOGO then you tend to make up the price difference real fast.  I’ve also gotten BOGO on roasts during barbecue season.
5. Price per Unit of Weight
   I can’t tell you how much you’ll save when you really pay attention to this.  Not every store will print the price per weight/unit, but if they do, compare your brands.  Yeah, pre-sliced apples are $1.99 per bag, but have you looked at the crazy price per ounce?  In comparison to an actual fucking apple you can pre-cut and dip in lemon-water and store in the fridge?  Don’t be a sucker.
6. Cook for yourself.
   Sure, it’s easy to buy boxed rice, boxed mac and cheese, frozen dinners…but just like the price per ounce, you’re paying for the convenience.  If it’s a case of “I just don’t have the time to cook” then learn a bunch of shortcuts.  Make more than one meal simultaneously.  Get a crockpot and/or rice cooker.  Pre-cut ingredients to keep at hand in the fridge.  You’ll save more money than you realize.
7. Be mindful of your calories.
   Who doesn’t love ice cream, chocolate, chips, soda, and other snacks.  Thing is, this is not necessarily nourishing food.  Your body demands vitamins, fats, carbs, and protein/amino acids.  A lot of the things we love to snack on do not satisfy the demands of our bodies.  Juice cocktails are loaded up with sugar; buy 100% unsweetened juice or, better yet, invest in a juicer.  Switch out your sodas with chocolate milk and/or tea/coffee, lightly sweetened and kept cold in the fridge after brewing.  Cut your juice with herbal or green tea.  Make your own chips and freezer meals.

I’ll add to this list as things come to me.  What are your favorite shopping tips and tricks?