My advice is to check out the fluff in 3rd (which, IMO, had the best fluff for gear descriptions) and the rest. As covert ops, you need to know (research!) what sub-culture you're heading into. Sure, the Sioux won't blink at an armored jacked or lined coat, but that's especially if it's buckskin-tailored; for them, there are wild and woolly critters out there that you need armor against just going around town. If you want to blend in with sararimen slumming or the orxploitation executive scene, you want the Sleeping Tiger line; if you want to blend with the avant garde and the quirky at an off-main art gallery, the Steampunk line might be best. If you're blending with low-level execs, the Synergist line; heading into the boardroom, though, you'll want Executive Suite.
An infiltrator can easily spend hundreds of thousands of nuyen to wear just the right gear in order to blend in. This is why I created the 'Mr. Cleaner' organization contact for my game - someone who rents out top fashion, 'line' armored clothing, and appropriate stuff with corporate logos and such on them, at a 100% deposit, renting at 5-10% value per day. A surcharge may be added if the clothing is returned with bullet holes or blood, but if it hits 100%, the armor is considered bought - it's yours, go fix it yourself.