A pigeon inquires,
As fall approaches and I’m looking at all the cute outfits everyone is posting, I need an opinion. Being a traditionally built woman, as they say in Botswana (read: curvy and left skinny a long time ago), is there any way I can wear boots in a flattering manner? I don’t even mean for Sunday. I mean ever. Skinny girls can get away with anything, but I have yet to see boots shown on a larger, curvier woman, or with an outfit that I think would be even remotely flattering, in any of the fashion posts. There are some super cute boots out there, but no leggings (as per your post), skinny jeans are out for some of the same reasons, maybe with a denim skirt? Maybe I need images. Or will boots just bulk up my lower legs. Or can I even find boots to fit?
Someone forgot to eat her Confidence Puffs for breakfast!
Girl. Of COURSE you can wear boots. Do you see yourself in boots? Can you imagine yourself in a pair of great boots swaggering all over town bringing the love ‘o God to all you meet? Why not? Boots come in a huge, almost infinite variety. There are ankle boots, thigh boots, cowboy boots, riding boots, motorcycle boots, Goth boots, and Go-Go boots! They’re round-toed, pointy, high-heeled or flat. They come in suede, leather, pleather, and vinyl. I would be a sad case without my boots, which are my fall/winter shoes of choice.
The thing to do is start collecting pictures. Think about boots you’ve seen on other women and loved. Is there a way to rock that look yourself? Go and start experimenting. Try some on. I could say, “Oh yes, a great pair of chestnut riding boots would be the perfect classic to wear with skirts and pants,” but I don’t know you. Only you know you.
Readers, please submit photos of yourself wearing boots to share with our Bootless Pigeon. Show her how you do it.
You can send them to me at my real first name dot my real last name @ gmail.com. If you can’t figure that out I just don’t know what to say.

They’re sometimes hard to find, but you can get wide-calf boots that are fashionable and attractive (not always the same thing!) — Check Macy’s on line.
Zappos is a great source for wide calf boots.
Actually, I don’t do the skinny jeans, but I wear boots under jeans. That is why boot cut jeans are made. The skinny jeans I have seen look a log like leggings, and we know what PB says about leggings. [Well, tall, long-legged gals can look great in skinny jeans, like with a tweedy blazer and a great sweater. – PB]
Duo Boots sell knee length boots (and other things) in various calf widths. They also have a great sale every year! UK company but will ship international
Context is everything, I guess, but out here in the Midwest, I wear boots. To meetings. To church. Everywhere. My favorites are red cowboy boots my daughter gave me to wear to her wedding. She wore boots under her wedding dress, too. Fat calves (me, not my daughter) are no impediment! And boots hide fat ankles. A little stacked leather heel is the perfect thing to add height without wobbliness. The ONLY thing I like about cooler weather is that I can break out the boots again. Go get some boots!
Another vote for DUO. They also have some great photos on their site, though as with most of the fashion industry they lean towards tall skinny models. But still, they give ideas of the kind of things their boots look good with.
They’re pricy but Frye boots work well for my very muscular calves 😉 You can sometimes find deals online! Also check sites like zappos and endless for reviews that state others find the boots too wide in the calves. Those are usually money!
Can she wear boots? Pshaw! Everyone can wear some kind of boot! There are ankle boots, lace up boots, flat boots, wedge heels…
I’ve got quite thick calves so I sadly don’t fit most of the knee high boots in shops, but there are ways around this (without spending a fortune on special wide calf boots). I had a victorian-looking lace up pair which I loved. I’ve always worn ankle boots under jeans or other trousers. I’ve found some stretchy or wide cut boots in stores as I’ve hunted around.
Also, dresses and opaque tights. I love wearing brown boots and brown tights (for example) with a knee length skirt. I think it’s flattering as it the boot doesn’t visually ‘cut up’ your leg.
Wait, I don’t think anyone said leggings were out. Only that leggings are not pants, and that you should wear them with a skirt that’s long enough that you would wear it by itself, weather permitting.