When she’s not working with big names like Lupita Nyong’o, Jennifer Hudson, and Hilary Swank, celebrity stylist Micaela Erlanger also divulges her fashion expertise in our Ask a Stylist column. From the best places to source vintage to the secret to finding your most flattering jeans, come back each week for a professional’s perspective.
A pair of great ankle boots is a must for every woman’s fall wardrobe. And a pair that’s stylish and comfortable is the ultimate goal. For me, I’ve found that all of my go-to ankle boots have one thing in common: a low, thick, stacked heel. This block-style heel lends a sturdy form allowing you to comfortably wear the boots all day long. Also, opting for natural materials is key because the fabric will organically stretch and form to your foot.
Shop my favorite ankle boots that are stylish and extremely comfortable.
Complete the look
Submit a style question for Erlanger in the box below, and check back next Sunday to see if she answers yours!
Opening Images: Collage Vintage; Style du Monde
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These $50 Old Navy Zipped Boots Are Just as Chic as the $1500 Pair I Have Been Coveting Since Last WinterThey're on sale for $30 right now.
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Looking Chic in Cropped Jeans This Winter Means Wearing This Boot Style and ColorElizabeth Olsen would know.
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Here's the Comfy Yet Incredibly Chic Boot Style Fashion People Are Already Wearing on RepeatThese make any outfit look more expensive.
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Forget What You've Heard—Ankle Boots Are Still In, and This Expensive-Looking (But Just $50) Pair Is ProofGrab them before they're gone.
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This "Ugly" Shoe Trend Is Officially Back From 2016—But This Time, It's BetterSpotted in London and NYC.
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This Is the 2025 Way to Wear the Ankle Boot Trend Everyone Bought 4 Years AgoPSA: Don't toss them yet!
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Forget Flats—Everyone With Good Taste Is Wearing These Boots With Jeans and a JacketPut these on your shopping list.
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Just a Reminder: *This* Is the Best Pant Style to Wear With Every Type of BootThey're model-off-duty approved.
