The Best Socks To Wear With Booties in the Winter

I get asked all the time what socks to wear with booties in the winter, so I wrote a post about it!

I know, it’s a conundrum. And let’s face it, ankle boots often look best with no socks, especially when wearing jeans that show a bit of skin.

But that’s not always practical, and I would never suggest you eschew socks for the sake of fashion, even though personally, I’m lazy and only wear them when it gets really cold.

Of course, some booties simply do not look good with socks — those with split shafts, mainly — and those I simply do not wear on the coldest of days.

These are a good example of booties I would not wear with socks.

But most booties can accommodate socks, and it’s fine if they show, as long as they work with the rest of the outfit. In fact, sometimes they add another element of interest that can really make the look.

Here I’m wearing AG Farrah ankle skinnies (they have a 28″ inseam) with Marc Fisher Yale Chelsea boots.

Marc Fisher Yale Chelsea Boots

On top, I’m wearing a chunky turtleneck, and I accessorized with a Victoria Emerson boho cuff.

This turtleneck is perfect for those who want a cozy sweater and can’t tolerate wool — the fabric is 55% cotton, 23% recycled polyester, 22% polyester. It’s cut generously, but I would still say it runs true to size; I have the small.

FYI, both Banana Republic and Victoria Emerson have extended their Cyber Monday sales, so this sweater is 50% off plus an additional 10% off with code BRCYBER, and the boho cuff is 50% off (no code needed.) Also, my boots are 20% off at Nordstrom, and the jeans are $50 off at Saks.

But back to the socks… Oh, they’re 20% off too! Gotta love it when Black Friday sales overflow into the next week!

I usually wear solid color socks that blend into my outfit, so if they show, they don’t really distract from the look. And sometimes, that’s the best way to go.

But I recently purchased these Smartwool popcorn polka dot crew socks to wear with my neutral looks when I want to add a little pop of pattern to the look. I picked up the black and the grey, and I’m wearing the black with this outfit.

These socks are currently 20% off at Backcountry; and you can also find them on Zappo’s, Nordstrom, Amazon, and

Not only do they add a fun pattern and texture to the look, but they’re Smartwool, so of course they are very warm.

FOUND: The Best Socks To Wear With Booties in the Winter!

Obviously, you can’t see them when I’m standing up, but when I sit down and move around, they do show, and I think the glimpse of pattern is really fun.

Of course, they also make solid colors for the times when you don’t want your socks to make a statement.

I have to say, from a girl who rarely wears socks, I was loving how cozy and warm my feet felt the day I wore this outfit. I may actually be a convert to wearing socks as a default from now on!

Eh… probably not. I’m far too lazy for that. But when I do need to keep my feet warm, Smartwool socks are going to be the some of the ones I reach for.

Jo-Lynne Shane wearing monochromatic outfit with Marc Fisher Yale Chelsea Boots

Shop the Post:

BR turtleneck (50%  off + add’l 10%) // AG jeans ($50 off) // Smartwool socks (20% off) // Marc Fisher boots (20% off) // Victoria Emerson bracelet c/o // Lagos earrings

Shop More Smartwool Socks to Wear with Booties:

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The Best Socks To Wear With Booties in the Winter

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photos: Alison Cornell