In my experience, the biggest cooking challenges many of us face are lack of essential cooking tools and lack of knowledge.
Most recipes require only a few sturdy pieces to get from instructions to completion: a sharp chef’s knife; a sturdy, clean cutting board anchored to the countertop; and a heavy-duty skillet, saucepan or Dutch oven. Gadgets and machines are nice, but are often space-wasters and not essential for most of your cooking needs.
I’ve been known to shop at Bed Bath and Beyond (with my stack of 20% off coupons), Kohl’s (also with coupons) and of course the upscale mall stores, though I think they are over-priced. Knives I have used and like include Henckles and my Anolon Santoku knife.
The most important features I look for are how the knife feels in my hand and whether the blade is covered completely, rather than exposed to prevent accidents. Look at how the blade meets the handle in the photo of my knives above, versus this one, sold on Amazon, which I would not buy:
Your cutting board should be sturdy and clean. Replace old boards if they are warped, cracked or deeply cut. To anchor to the counter, simply place a very damp paper towel or dish cloth on the counter and position your cutting board on top of it. This will prevent it from sliding around.
As far as pots and pans, I have used and liked Calphalon, Cuisinart, All-Clad and t-fal. At home I have a very large nonstick Calphalon skillet with a helper handle (essential for when that pan is hot and heavy) that I bought at Williams-Sonoma, and a set of t-fal saucepans with clear glass lids that I got at Kohls.
As far as knowledge, I recommend learning from friends or relatives, or taking a basic cooking skills class like those offered at Sur la Table, the Culinary Underground in Southborough, or an adult-education program.