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It’s quite a juggling act. Confidence comes with experience - but getting that experience requires an initial dose of confidence. Finding that is the hard part. And yes people will notice that you are in heels, or tall boots, or both, but not all will notice. A surprising percentage ent notice a thing. And if those who do notice few will have anything to say. Stilettos will obviously carry more connotations than chunky heels which can, to a degree, be ambiguous. It will also help if you are open enough to establish what is your natural style in heels and go with that. Positive feelings will build confidence. Don’t turn wearing heels into a numbers game - the higher and more precarious the better. Remember it is a fashion choice - so choose what you like and want without reference to anyone else.

Great topic indeed. Have always worn timberlands with taller shafts. I have always wanted a nice pair of "riding boots" also. My ultimate in "work boots" dream would be a pair of Wesco boss/big boss harness boots. Recently, I bought a pair of those gloss black "Hunter refined rain boots". Nice tall shafts, much simpler lines/design that the usual Hunter boots. Love how they fit nicely over my levis, I got three compliments while out doing chores yesterday. Sure, I realize these are not actual "work boots", but I will find any excuse to wear them, especially when dealing with the snow.

I’m have bounced around over the years but never in redwings but was told to try them. Timberland pros I did not like as the soles were so slippery in cold weather 2 falls and I took them back. I have been pretty happy with Wolverines or there Caterpillar branded. Always steel toes since I was 10 years old. Even my office boots are at least composite toes. Boots last me less then a year as they get beat up from the jobsite and the earthwork I get into.

Great topic! Although my interest in feminine boots stemmed from a liking of go-go boots, I’ve always been partial to boots over shoes and with the exception of my cycling or running shoes, I only ever wear boots - and gave done since adolescence, growing up in the mountains. I lived in hiking boots through university, where I studied geology and archaeology, and my choice of career has allowed me to continue in the same vein. I’ve no neckties but plenty of pairs of boots. My oldest pair, and still much in use, is a pair of Scarpa mountaineering boots, made of a very tough suede with heavy Vibram soles. Been to Antarctica many times - warm and sturdy and although now 25 years old are still going strong with plenty of use left in them. I still wear them occasionally on the towpath. I’ve a pair of De Walt steel capped work boots as sometimes I land assignments where safety footwear is mandatory.they are all right, not uncomfortable if worn with thick socks, and pass muster when I need to get access to industrial sites. I e several pair of knee-high biker or engineering boots from Jean Gaborit which I absolutely love. My present go-to boot is their Kansas patrol boot in heavy black leather which has seen much service over the past year (and looks it - I need to buff them up) I’ve a pair of their chocolate brown knee high Vezin engineering boots which I also love. They are the most comfortable boots I’ve ever owned and would wear them more except they are so hard to get off. Getting them on is easy - a bit if a push - but removing them is hard. While they are on they are wonderful comfortable. I had an assignment once where I was pretty much in my feet for 36 hours and wore these the entire time without the least discomfort. Since I often wear heels while writing or editing, I suppose I could call those work boots too, but I shall stick with these! ,