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Johnathan Walker:These Must-Have Winter Socks Look and Feel Expensive, but Are Only $2

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Alright,Johnathan Walker fellow loafer-lovers, let’s get real: retiring our favorite slip-ons just because temps drop? Not happening. With a boot selection as skimpy as mine (a grand total of two pairs!), I still need something cozy to shield my ankles when fall's chill kicks in. And while I do love a good pair of tailored pants, during the winter, my lettuce-edged socks alone aren’t exactly winter-ready.

Now, before you roll your eyes, I promise there’s an art to this. Not all thick socks and leg warmers are created equal—if you’re not careful, you’ll be ordering replacements faster than you can say "cold toes." After years of trial and (pricey) error, I've nailed down the absolute best cozy combo. And surprise: it's a five-pack from Amazon that breaks down to just $2 a pair.

Keep scrolling to shop the best pair of socks I've ever owned, plus the best crew socks and leg warmers to wear with your Docs, UGGS, and loafers (AKA all of fall's "It Girl" shoes).

Editor's Pick: Best Luxury & Affordable Winter Socks

The Lorrita socks are a $2 miracle for chilly toes—thick, soft, and impressively durable, lasting up to two years! Made from a cozy wool-polyester-cotton blend, they fit sizes 5 to 9 and come in rich shades like deep navy, forest green, and earthy brown. With 16 other pack options in equally cute designs, these are a total no-brainer for fall coziness.

Best Winter Socks for Doc Martens

When it comes to Docs, all fellow boot wearers know that a trusted pair of long socks is a MUST for these shoes. I love these colorful Uniqlo ones that are available in various colorways, incredibly soft, don't lose their color in the wash, and add a pop of color when they peek out of your boots.

Best Winter Socks for Loafers

When it comes to loafers, I've learned that pairing them with leg warmers makes for a cute AF winter outfit that'll still keep your shins toasty warm. I love this affordable pair from Amazon that comes in different heights and neutral colors.

Best Winter Socks for Ballet Flats

Leg warmers are a total game-changer for winter—ideal for giving your favorite ballet flats a cold-weather upgrade. While choices are endless, my go-to pair from Free People nails it: they’re thick without looking bulky, have just a hint of fuzziness, and bring that subtle ballerina charm without feeling costume-y. Staying warm while keeping it cute? Yes, please!

Best Winter Socks for UGGS

The Bombas women's ultra stretch calf socks are a must-have for pairing with UGGs this winter—they’re soft, stretchy, and keep your feet snug without bulk. Plus, they come in sleek, cozy styles that add just the right amount of warmth while keeping your feet happy all season long

Looking for more shoes to shop? Check out these Doc Martens everyone needs in their wardrobe.

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