Confession-I don’t love booties (on me) I wear sneakers and flats (pointy toe, loafer) as long as possible, and will even wear sneakers in winter if I don’t have to wade through slop. When sneakers are not an option, I’ve got one pair of low heeled booties, and one pair of high boots (pictured below). Problem is, I find there is something ‘off’ when I wear my booties with my usual silhouettes.

My favourite silhouette is an ankle baring cropped pant. Alternatively I’m into a knee covering skirt or dress, or a straight leg pant. With the straight leg pant, the bootie looks like an ordinary almond toe shoe. I can’t put my finger on what is wrong with the ankle baring looks. Flower pot? I have curvy calves and thighs, but narrow ankles and knees.

The very low heel of the booties is perfect. I can’t comfortably go higher. Can you help me with some styling tips and/or bootie recs? I’m not adverse to adding a new pair of booties (maybe cognac like the JCrews in Angie’s picks?) but need the lowest of heels possible. I’m also open to considering different bottom silhouettes or socks/tights combinations that will make my current booties work. I STRONGLY BELIEVE that footwear can make or break a ‘look’, and I want to get this right!

I like tall boots even less, but have included pics of the ones I have. Other than the equestrian look (when I wear the boots all day), I wear the boots until I reach my destination (when I change out to shoes.) I had the heels of the tall boots lowered (!) and as a result wore them more last year.

I am open to just about anything! Please help,

#1/2 Town Shoes booties, Franco Sarto tall boots
#3/4 silhouettes with booties
#5 silhouettes with boots

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