sock boots outfit

The Best Shoes To Wear With Jeans? Get Inspired by These 4 Sock Boot Outfits

Please note that this post may contain affiliate links and any sales made through such links will reward us a small commission – at no extra cost for you.

Sock boots are not necessarily a new and current fashion trend. They reached their peak popularity a few years ago and up until recently, have been considered dated. And the current trendy boot styles that have been taking their place are mini Uggs, Dr. Martens, chunky lug sole Chelsea boots, and slouchy over-the-knee boots.

But celebs have been pictured wearing this style again lately, from knee sock boots to sock booties, leaving trend forecasters from WhoWhatWear keeping them on the radar of the fashion industry. But even if their popularity wasn’t potentially on the rise, I’m a big believer in wearing what you want even if it’s not “in”.

And though these black sock boots will never replace the classic ankle boots, I think they are a solution to a problem that many people ask: “What boots do I wear with jeans?”

I wanted to show you not just one, but 4 different ways you can wear these boots with different clothing pieces as well as why they may be worth adding to your wardrobe!

1. With Slim/Straight Leg Jeans

sweater | boots

For a casual look, pairing these boots with jeans and a simple sweater is always a good idea. Though if you wanted to dress up this look, you could simply add a long coat over it. This combo is a favorite sock boot outfit of mine. Slim jeans and sock boots are a perfect match!

And though on the pricier side, I’ll rave about this specific pair. They really do fit your foot like a glove and they are very comfortable to wear, even with a small heel. I especially like that they make the confusion of what boots to wear with jeans so easy. These calf-hugging shoes slide right under your jeans, looking like a perfect fit.

With that being said, you know the fit of your boots is right when they hug your calf without digging into it. The knit material should feel comfortable around your leg, not too tight. But at the same time, the purpose of these shoes is that they are slim, so if the top of your shoes is too baggy then it won’t work.

For a no-fail straight-leg jeans and boot combo, try these sock boots!

2. With a Dress

dress | boots

Because of the knit sock material, sock boots outfits may seem like they should mostly be casual, but you can wear this wardrobe piece with classier items too!

This type of boots outfit can be a look that you could wear for Thanksgiving, date nights, or work.

3. With Pants

blazer | boots

The perfect way (well, one of them) to wear these shoes is with wider pants because this fitted shoe style pairs well with roomier bottoms. Pairing these slim boots with wider bottoms creates a nice juxtaposition.

When shopping for these shoes, keep in mind your body type, whether you’re shorter, taller, or somewhere in between. You want to make sure the top of the boot hits you on a spot that is flattering on your leg instead of cutting you off.

Related: What To Wear With Plaid Pants for an Updated Classic Look

One con that I can think of with this style is that they may not be the most flattering if you have bigger feet. I’m wearing a size 10 and they certainly don’t make my feet look any smaller, but that’s not my goal.

If others don’t want to look like they have bigish feet, then it may not be the shoe for you.

From a midi skirt to a mini skirt, maxi dress to wide-leg pants, these boots can be worn with a variety of different styles, but they don’t pair that well with skinny jeans. Unless your skinny jeans are skin tight that is, as you don’t want any bulkiness under or over your boots and jeans combo.

On that topic, when it comes to what socks to wear with them, the best socks to wear would be thinner socks. You don’t want anything too bulky like wool socks or anything that could potentially add bulkiness to your upper calf like tall socks.

I love that the block heels keep these shoes from actually looking like socks while the knit fabric offers all the comfort that socks do.

I think this is the perfect choice when you are looking for boots to wear with jeans that will also keep you warm and protect your ankle from the fall and winter elements.

To have these boots look as classic as possible instead of trendy, choose them in a neutral color. Black boots are never a bad idea or any other similar neutral-colored sock boots.

But of course, if you did want to treat these boots as a trend and add a pop of color to your outfit, choose bright colors instead.

newsletter sign up resource library

Another shoe style that’s not necessarily “in” but practical for the colder weather is the over-the-knee boot. Check it out: An Over-the-Knee Boots Outfit To Inspire Your Cold Weather Dressing

sock boots outfit
sock boot outfit


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.