Aetrex Amber Sweater Boot is like a sweater for your legs except it’s appropriate for the office. The sweater material provides stretch for large calves, comme mienne, and follows the Aetrex Healthy 3 – built-in orthotics for support, memory foam for comfort, and anti-microbial technology for odor free greatness.

Grenson Cora boot comes from the Triple Welt collection that highlights former Grenson silhouettes. This style in particular undergoes a process called “Chromexcel” because it goes through 89 different processes and takes 28 days to create at the Horween Tannery. The Chromexcel technique was developed over a century ago. So, I mean, if they’re still doing it the same way, they must have conjured up something special.

BED|STÜ Isla can be worn with anything, to just about anywhere. There’s an inside zip that is unbelievably sturdy, and leather construction so well-made you’d swear it was made specially for your feet. Typically for structured, heeled boots, it’s a few wears for my toes to no longer feel pinched, but the comfort is instant. Just a forewarning, like every non-rubberesque sole, don’t walk around on carpet with them on. Scuff them up on the concrete streets first so you don’t go slipping around like me.

If there’s an over the knee option, it’s usually not comfortable. Rockport Total Motion Over Knee Boot has sex appeal and the ultimate in comfort technology with their ADIPRENE® and ADIPRENE®+ by adidas sport technology for all day feet lovin’. The retention foam helps provide contact and support for feet, and soft materials ensure a glove like fit without the feeling of compression. It’s a win-win for both your body and your closet.

Can’t promise you’ll be considered a martyr in these Sorel Joan of Arctic Wedge Mid, but you’ll definitely be embarking on some risqué and respected fashion choices when styled to your liking.  Inspired by the one and only Joan d’Arc, these boots are comprised of waterproof, full-grain leather with burnished accents; ideal footwear if your intentions were to actually help save the world.

EMU Australia Featherwood Hi Merino wool insulated boots are like having the warmest, coziest blankets wrapped around you as you walk. As temperatures drop, all we want are heated throws to snuggle up with in-between meetings, events, and life. Sadly, that’s unrealistic so we’ll compromise with the next best thing.

Clarks® Pita Austin is part of their Artisan collection offering waterproof performance without skimping on the aesthetics. This rust leather boot has side zip for easy entry,  OrthoLite® footbed for all-day, every-day walking, and sturdy rubber outsoles sans scuffing. Wear it in the rain or sunshine… you’re safe!

Jack Rogers Olivia Suede scalloped edging is a sleek option for the boots this season. A rotational piece for much of the year, it laces up front and comes with a 3 ¼ inch stacked wedge for some height. Height that goes from day to night with little to no effort, in shades that transition just as seamlessly.