For us shorties, finding the right pair of fall/winter shoes is often a challenge in itself. We want a shoe that gives us height (so we don’t look 12 years old), a shoe that looks professional (so we’re taken seriously at work) and a shoe we can wear on weekend errands and nights out (so we actually look our age at the bars and not get questionable stares from bouncers).

Over-the-knee styles cover half our stems, and flat Chelsea boots make our feet look like elves (or maybe that’s just me). And while flats are great year-round, we need every ounce of extra inches to look like the sharp and fashion-savvy twenty-somethings we are. Even if it wasn’t in G-d’s plan to grace us with a bigger boost after our growth spurts (take it from me–my mom is 5’6″ and my dad is 6’4″–that left me at…5’1″), these boots will make you feel powerful as you get in line with every normal-heighted person.

The solution? The ankle boot.

Whether tucked in with skinny or cropped jeans, skirts and dresses, or even simply an oversize sweater and leggings–a boot that hits at or just above the ankle has us covered. Here are 15 awesome styles 2 1/2 inches and higher and under $100 to add to your closet:

Bandolino “Adelun” Black Leather Ankle Boots, $99,

Heel height: 2 3/4 inches, plus extra 1/2 inch platform

bandolino boots

Madden Girl “Sharpen” Taupe Paris Boots, $59.95,

Heel height: 3 1/2 inches

madden girl boots

Hush Puppies “Corie Imagery” in Tan Leather, $99,

Who knew the brand known for those awkward loafers (often found at Famous Footwear) actually makes cute ankle boots? Comes in six other colors and available in both medium and wide widths.

Heel height: 2 1/4 inches

hush puppies boots

Toms Navy Embroidered Women’s Desert Wedges, $66.75,

A cool design for weekend styles, plus Toms gives a pair to a child in need. A win for your soul and your sole.

Heel height: 2 3/4 inches

toms boots

Sole Society “Erlina” Women’s Suede Bootie in Army, $89.95,

The gold stud detail toughens up a basic style.

Heel height: 3 1/4 inches

sole society erlina boots

Sole Society “Roxine” Women’s Suede Bootie in New Navy, $89.95,

Your new favorite blue suede shoes.

Heel height: 2 3/4 inches

sole society boots

Sam & Libby “Marley” Ankle Boots in Putty, $39.99,

Designer for less and under $50.

Heel height: 2 1/2 inches

sam and libby boots

Steve Madden “Whysper” Black Nubuck, $99.95,

Steve is my man for all seasons. I can count on his ankle boots in the fall/winter, patent flats in the spring and beaded sandals in the summer.

Heel height: 3 inches

steve madden boots

BP “Train” Wrap Belted Bootie in Chocolate/Chocolate, $99.95,

Comes in two colors and in sizes 4-13.

Heel height: 3 1/4 inches

bp train boots

Sperry Top Sider “Harlow” Bootie in Grey Suede, $99.95,

The rubber wedge will make these perfect for walking in the snow.

sperry top sider boots


Old Navy Women’s Strappy Ankle Boots, $26,

Under $30–these are a total steal.

Heel height: 3 inches

old navy boots

Aldo “Celia” Ankle Booties in Black Suede, $90,

The lace-up oxford gets a lift.

Heel height: 3 inches

aldo boots



Hannah Gettleman is a bubbly twenty-something living in Chicago. She graduated in 2012 from the University of Illinois at Urbana-Champaign with a degree in Journalism. Don't tell her that print is dying--she's already made the switch to public relations. As a Midwest girl, winter happens approximately 80% of the year, so she knows a thing or two about a good pair of snow boots. She lives for summer weather (even though she can never tan), Boy Meets World reruns, and an unhealthy addiction to dark chocolate and online shopping. She's a die-hard Chicago sports fan, even though she's well aware the Cubs always end up in last place every year.

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