If I had to wear a specific type of shoe for the rest of my life, it would be boots. Heeled, flat, wedge, short, tall, I love them all. As of late, I've been really into over the knee boots. They add an instant chic factor to any outfit, whether I'm lounging around my house or going out with friends.
Still on the hunt for a good sweater dress. One of my online obsessions is this turtleneck dress from Revolve. When a hemline is short, the boot length should be high...in my opinion. I actually just bought these boots from ASOS and I am very much enjoying them. Heeled tall boots are really fun and extremely sassy. Channel your inner Gigi Hadid and pair this ensemble with a belted black coat.
An oversize sweater (preferably cable knit), fall-inspired scarf (look at Madewell for the perfect plaid scarf) and comfortable skinny jeans (my favorites are AG or Seven) are a classic fall outfit made even more perfect with a pair of OTK boots. To stray from my black go-to's, I chose a pair of tan Stuart Weitzman suede boots. To me, Stuart Weitzman is the best place for OTK boots. Unfortunately, they're a wee bit pricey, so invest well.
I bought the leather 5050 boots in the beginning of the fall season, and they're truly a pair of shoes to wear for years. They're unexpectedly comfortable, and I actually wear them quite a lot. When I have sorority chapter on Monday nights, I usually pair a skirt/sweater or dress (like this great option from BB Dakota) with the 5050 boots. If it's cold, wear tights, if not, bare legs are fine too.
I wear OTK boots a lot when I'm going to bars. I'm crazy obsessed with ASOS and all their going out tops (actually really eyeing the one shown in the collage above). Keep it cool by wearing black jeans and then spice it up with heeled grey-tan boots. Again with the heel! These are Stuart Weitzman, so quite expensive, but ASOS has a nice alternative as well.