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I just completed my quick 1.5-day trip. And @pebblesf, the airline was SWA. I wore my Jessica Simpson black faux suede with block heels both ways. Stilettos would have been a nightmare of the airport floors. First with jeans and returned in dark red cords. I was one of the very few in colors other than white, black, blue, grey, and beige. Also, I had the highest heels everywhere. I saw some SWA flight attendants in short (2 inch) heels, and a Spirit FA also on short heels at the hotel I stayed at. Almost all the CLEAR and TSA agents complimented me on my knee-high boots before saying anything else. The guy at the car rental also complimented me on the ‘fierce’ boots before I got to his station. At least 20 other travelers also complimented me on the boots. Many, many double takes. Good quick trip. Another trip in a month. Again boots

These (from M&S) for example?

I would say that Chelsea boots can be flat, or have Cuban, block or stiletto heels. The 'Chelsea' aspect seems to relate to the elastic sides, although zip-sided boots are also called 'Chelsea' style. These (Calvin Klein) are sold as 'Chelsea boots' (and would surely look good on many men):