What Socks To Wear With Chelsea Boots?

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The wildly popular Chelsea boots are a great ankle height, but what socks should you wear with them. We’ve looked around at examples and asked the experts what they have to say. So here’s a list of super socks for Chelsea boots.

The best socks for Chelsea Boots are –

  • Trouser socks
  • Crew Socks
  • Fuzzy Socks
  • Sock Stockings
  • Winter Socks
  • No Socks At All

Let’s take a look at each of these cute options. We’ll also talk about how Chelsea boots should fit if they’re easy to put on, and why in the world they are so popular. So please, keep reading.

Blue cotton crew socks on beautiful woman's feet. Isolated on white background, What Socks To Wear With Chelsea Boots

Super Socks For Chelsea Boots!

Socks are a handy little part of our wardrobes. They keep our feet warm or wick moisture in the summer. Socks make our shoes easy to slide on and keep them from sticking. They occasionally lose their partner in the wash, but then we have an excuse to buy another pair. And who doesn’t love a new pair of socks? Let’s look at what you might wear with Chelsea boots.

Trouser socks

Because Chelsea boots are ankle height, you want a sock that will be slightly above the top of the shaft. Anything lower might tend to bunch or droop. Trouser socks are essentially crew height socks but thin enough to wear as dress socks. If you have a fun skinny, tight pair of Chelsea boots that you wear with a dapper suit, trouser socks are a fantastic choice.

Here’s a nice pack of three trouser socks in navy patterns. They’ll work with jeans or slacks.

Click here for these on Amazon.

Want something luxurious? These cashmere/merino wool blend trouser socks will give added warmth and softness for cooler temperatures. These are luxurious socks.

Click here for these on Amazon.

Crew Socks

Crew socks are slightly taller than trouser socks and hit between the knee and mid-calf. They come in a wide variety of styles and thicknesses, and materials, so you can style your Chelsea Boots anyway you want with this type of sock. We’ve found a couple of favorites to share with you.

Here’s a practical 4-pack of sporty crew socks to wear with your Chelsea boots. These socks from Hanes are affordable, soft, and wick moisture away from your feet. Each pair has a different color heel and toe patch, which helps when you match them up out of the dryer.

Click here for this on Amazon.

Ugg makes these adorable slouchy rib-knit crew socks. Put them on, then push them down for distinctive styling with your Chelsea boots. They come in 10 different fun colors, including this red color.

Click here for this on Amazon.

Fuzzy Socks

Everybody loves a tall fuzzy boot sock in the winter. If you wear your Chelsea boots with a long skirt, these tall socks will add warmth and flair to your fashionable look. Make sure your boot fit allows for a thicker sock, or try to find a pair with thinner soles and a thicker rise.

These six-pack of colorful fuzzers is all stripes and pizazz. You’ll have stripes for almost every day of the week.

Click here for these on Amazon.

These knee-high fuzzy socks are perfect for wearing with skirts and Chelsea boots to give you cute coverage from the winter chill. This brand is available in several different patterns and styles, but this set includes a neutral gray and a banded white pair.

Click here for these on Amazon.

Sock Stockings

If you want the feeling of no socks, but don’t want your bare foot in your boot, then consider a pair of stocking socks. These are the shape and size of a sock but made out of hosiery. They slip easily into any boot and are perfect for work.

These knee-high stockings from Hue are opaque black and perfect to wear with your Chelsea boots. This is a 4-pack and is available in black or espresso.

Click here for this on Amazon.

Winter Socks

Winter socks come in pretty much all of the varieties above but are often made of wool or other warm materials like cashmere or lambswool. A combined pair of Chelsea boots with high-quality wool socks is a can’t go wrong duo.

Click here to see this on Amazon.

Smartwool makes great socks for winter. They are warm, wicking, and not so bulky that they’ll create an uncomfortable fit for your shoes. This snowflake pair is absolutely adorable. Pair it with the red gore Blundstones for an awesomely fun look.

Click here for these Blundstones on Amazon.

No Socks At All

There’s nothing that says you have to wear socks with your Chelsea boots. Plenty of people don’t, and the look is adorable. Some people like to wear their Chelsea boots through the summer and don’t want the added bulk of a sock. But if you can’t stand the feel of bare feet in shoes, then you could consider some little foot protector socks.

These air cushion Hue foot liners allow you to have the look of a bare foot but still have some protection on your feet. You never know when you might need to slip off a shoe, so these are the best of both worlds.

Click here for these on Amazon.

How Should Chelsea Boots Fit?

Chelsea boots tend to run pretty true to size. The gored elastic at the sides gives them an easy stretch for pulling on and off. You want them to fit fairly snug around the ankles without a huge gap. If they are a bit loose, choose a thicker pair of socks to keep them from sliding on your foot or ankle. You can also add an insert to the footbed if your boots are a half size too big.

These heel inserts are designed to size your shoe down by half a size.

Click here for these on Amazon.

Are Chelsea Boots Easy To Put On?

Chelsea Boots should be pretty easy to put on. They have elastic gores on the sides that help stretch out the opening to slide your foot into. Many of them also come with a tab loop at the heel to help you pull them on. If the shaft is a little bit tight when you first get them, you can always get a leather stretch spray to help widen it for an easy fit.

Leather stretch spray is designed to spray onto stiff leather boots just before you wear them. It aids in softening and giving a subtle stretch to new, stiff leather.

Click here for this on Amazon.

Why Are Chelsea Boots So Popular?

Chelsea Boots have a long history. Worn by men and women alike, they hail back as far as the Victorian era when Queen Victoria asked for no-lace boots that wouldn’t get stuck in her stirrup when she rode. Known then as a paddock boot, the Chelsea boot has evolved over the generations as a classic ankle boot that can go from business casual to rock star chic.

Here’s a classic slip-on Chelsea boot from the popular maker, Blundstone. This has side uppers and a synthetic sole. Fits true to size.

Click here for these on Amazon.

A Pair, Or Two, Or Three

With all these choices for great socks with your Chelsea boots, the choice might be hard. Why limit yourself? Fill one from every category and have endless ways to style your classic boots.

If you enjoyed this post here at StyleCheer.com, please check out a few of our others we think you’ll love!

25 Types of Boots for Women [A Fashion Guide]

How To Wear Chelsea Boots (9 Suggestions For Women)

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