Shoes with leggings?

I wear comfortable tall boots and also something like this www.sandler.com.au/festival.html#185=145 mine are less bulky than this and the metallic is slightly less shiny. My dd talked me into buying them and I didn't think I'd wear them much but I do and they look really good with leggings. I'm always getting comments on them.

Tall boots or flats.

Clogs scream old lady.

Today at work I wore leggings, a tunic, and a pair of black suede loafers. They are Born brand and comfy for my old feet. Sometimes booties. I personally don't like tall boots on me.

Plain ballet flats or vans. Dependent on the tunic or top I'm wearing with them.

I live in leggings because I'm a SAHM and I'm lazy   

My footwear throughout the year runs from flip flops to ballet flats to cowboy boots to Uggs   

Boots or booties. Ballet flats look nice too, but I wear those to work with dresses so much that I get sick of them.

I have the same problem.  I did find some tall boots from Simply Be that are extra curvy plus that fit me.  And they are reasonable priced.

Absolutely.  I am no spring chicken myself.  That doesn't mean I necessarily agree that "clogs scream old lady" though.  

If I'm wearing leggings I generally have in a hoodie or other sweatshirt and wear tennis shoes.

In the cold months I wear riding boots or ankle boots (I have several different types/styles). It really depends on what top I am wearing. I try my best to look "current" when I walk out the door.

Indeed they do. I don't really see people wearing leggings anymore.
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I've had this challenge, too and like you summer is easier with sandals. For winter I do boots. For fall, I finally found some loafers that fit me across the ball of the foot - Coach on sale at Steinmart. They aren't for a lot of walking as they have no support, just found a more supportive pair at a consignment shop so I'm giving those a try. I gave up on ballet flats because of the lack of support and they never completely cover my toes. People who make ballet flats should realize that you can't just add length in the middle of the shoe for larger sizes.

Shoes are my nemesis and I often choose clothes from the feet up working first with what shoes are going to be comfortable. Good luck, I hope you find shoes that work for you.

I answered yesterday too, but today I am wearing leggings, a tunic, and Clarks WaveRun casual shoes in black. These are extremely comfortable shoes for a day I anticipate being on my feet until 9pm tonight.

Footwear depends on what is paired with the leggings. For example, I wear clogs with leggings, a basic tee-shirt, & casual cardigan. If I change to a dressier shirt &/or blazer, I wear oxford mules. Athletic sneakers, slides, or colorful Converse are worn with leggings, a tank top, & lightweight/running jacket.