During the winter, warm socks are a must! But it can be tricky to figure out how to wear tall socks with boots and keep your outfit still looking great. Here are a few tips.

How to wear tall socks with boots

Taller socks are a great way to keep your feet warmer in the winter. If you’re trying to figure out how to wear tall socks with boots, I’ve got a few ideas below!

A couple of weeks ago I did a post about Chelsea boots, and a few of the outfits had tall socks layered under the boots.

When I talked about it on Instagram, I got lots of questions from you guys about how to wear tall socks, so today I want to show you how to wear tall socks in different outfits.

1. Tuck your skinny jeans or leggings into tall socks

The key to this look is choosing pants that are super fitted at the calves AND long enough to fully tuck into the socks so you don’t deal with bunching or shifting throughout the day.

A few other helpful notes about this style

• I’m wearing THESE SOCKS, and they’re a perfect height
• Don’t pull your socks too high. One to two inches above the top of your boot is best so you don’t break up your leg line in a funky way.
• My favorite everyday leggings that are thick and opaque and comfortable, are also very long and great for tucking into socks. These are them.

2. Wear your socks underneath your pants hemline

If you’re wearing a different style of jeans or pants that isn’t skinny or fitted on the leg, you can absolutely wear socks underneath them.

A few helpful notes about this style

• Thinner socks are better than thick, chunky socks with this style. The thicker the sock, the thicker your ankle becomes, and that can easily make your leg look blocky. THESE SOCKS are super warm, but aren’t chunky.
• Try leaving a small gap where the sock is exposed (just as you would leave an ankle gap). That gap gives some room to breath between the hem of your pants and the shaft of your boot, and keeps your leg from looking blocky.
• Any color sock works here – just pay attention to how the sock blends in or contrasts with your boots and the rest of your outfit. Do you want it to blend in and appear as part of the boot? Do you want it to contrast and stand out a bit? It’s your choice — just be aware of how it affects the rest of the outfit.

3. Try socks and boots with a skirt or dress

In the winter, sometimes a dress or skirt is a necessary outfit. But you can add a little extra warm with some tall socks and boots.

A few helpful notes about this style

• Let only a small amount of sock show above your boot. 1″ is good!
• You can try any color of sock here, but pay attention to how the sock color contrasts against your boot and your skin. I chose a gray against a black boot, because the boot and my skin have a large contrast, so the gray creates a nice transition from one to the other.

I hope that’s helpful as you keep those feet warm during the winter!

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