Styling Crop Straight Jeans for Winter

I’m watching the trends evolve, and I’m here to tell you, the straight denim trend is finally hitting mainstream. What’s more, it’s here to stay for a while.

Of course, we should all wear what looks best on us, and I’m not kicking my skinnies to the curb, but I’m going to try to integrating this style into my outfits more as we head into spring.

I’ve been analyzing others who are wearing this style, and there are a few factors to help make crop straight jeans work for you.

#1. Proper Length is Key

Everyone is different, but at 5’5″, I personally need a 25″ or 26″ inseam. Any longer, and it looks like I’m wearing floods. My ankle-length skinnies are typically 27 or 28″, for reference.

It’s hard to find a 25″ inseam, but 26″ is pretty popular.

The Agolde mid rise straight jeans I’m wearing in this post have a 26″ inseam. They’re almost ankle-length on me, but I think they work. I just have to work a little harder to make sure my shoes work with them and not against them.

Also notice that my jeans are not super wide. Some girls can get away with that, but I like a slimmer fit. These have an 12″ leg opening, so not a whole lot wider than my skinnies, which usually are 10″.

Incidentally, these jeans are amazing! They are thick and super soft and hug the body in all the right places. Best of all, they have great shape retention and don’t bag out as you wear them. They’re TTS, or size up if in between; I have the 29.

#2. Choose the Right Shoe

As far as shoes are concerned, I like sock booties with crop jeans in the winter because you can wear heavy socks, and no skin is exposed.

Sock booties have a high shaft and fit very close to the foot, so they keep the ankle area slender, which helps offset the extra width of the straight-cut jeans.

A pointed toe also helps keep you looking long and lean as well.

Style Tip: Your jeans should extend over the sock booties by at least an inch, so when you sit, you still get good coverage.

I recently purchased these Jeffrey Campbell Siren booties, and I love them. They have a padded footbed, and the neoprene material is super soft against the rest of the foot as well, and the shaft is soft and flexible too so they don’t rub you raw if you aren’t wearing tall socks.

These have a 3.5″ heel, but I find them very comfortable. Here’s a lower heel option, and a budget option.

You can also wear a more traditional bootie with a mid-height shaft, and in this case, they look best when the jeans just barely meet the top of the boot, but don’t “buckle”. That means, you may need an even shorter inseam, or you’ll need to cuff.

I recently ordered these Goodthreads crop straight jeans from Amazon, and they have a shorter inseam than the Agolde, even though it says 26″ online.

They work pretty well with my Marc Fisher Chelsea boots, whereas the Agolde are a little too long for them.

This is the Agolde…see how the jeans get caught on the back of the boot? (They do this on the front too.)

And here’s the Goodthreads jeans with the same boots…they just barely meet the top of the boot. This is a much better combination.

Another shoe that I like with straight crop jeans is a loafer mule.

These work because they expose a few inches of skin at the ankle, which is also slimming, and they usually have more of a pointed toe, which helps elongate the line of the leg.

Of course, if it is super cold where you are, you may have to wait a few months to wear this look, but I wanted to show a non-boot option.

Regular loafers work too, but I find the mule more feminine somehow, and a little more fashion-forward. I know some of you don’t like them, but if you do, they’re a great option, especially as we head into spring.

You can do a sneaker for a more casual look, just make sure the jeans are short enough to expose a few inches of skin in the ankle area. I like the length of the Goodthreads with sneakers.

#3. Your Top Matters

Your top is the other crucial piece to the puzzle when wearing crop jeans. Most people talk about what shoes to wear with crop jeans, but I rarely see them address the top!

I think this has been the most frustrating part of the crop jeans trend for me. I can’t just throw on any sweater in my closet with them and have it look right. Here’s why:

You are shortening the line of the leg by wearing shorter pants, so to keep a proper balance (1/3 to 2/3 is ideal) you have to also shorten your top.

This means tucked in, or at least a front-tuck.

The sweater I’m wearing here is already on the shorter side, and it fits fairly close to the body, but I still gave it a front-tuck. It helps that it is a thinner knit as well. (Unfortunately, it’s old and no longer linkable, but this is why sweater styles are getting shorter.)

If you’re busty, like me, tucking isn’t always the best look, so it takes a lot of trial and error to find the right combination of tops, jeans, and footwear to make it work.

Funny thing, though. When skinny jeans started to get popular, I felt the same way about them. It will get easier the more we play around with this silhouette.

I completed the look by adding my black leather jacket.

This is also an older piece, and therefore unlink-able, but I really like the front center zip as opposed to the asymmetrical zip and large lapels that is common with so many moto style jackets.

Not that I never wear that style, but it’s hard to find ones that don’t make me look top-heavy. This one is a good option (same brand as mine, butter soft leather!) And I like the looks of this one and this one as well.

Finally, I added a belt and a red bag to complete the look.

I really love this outfit, what do you think?

Styling Straight Crop Jeans

I played around with both the Agolde and Goodthreads cropped straight jeans one afternoon this week, and here are some more outfits I came up with…

Here’s one that does NOT work. The shoes are great, but the sweater is too long, and it’s awkward front-tucked with the split hem.

This sweater is a thinner knit, and it’s a little on the cropped side, and I feel like it works. Unfortunately, it’s sold out.

I like it even better with a front-tuck, but it could use a belt.

This one works okay too, with the Siren booties and Naadam scoop sweater. (This sweater finally went on sale! I’m wearing a small.)

This is another sold-out sweater, but because it’s cropped, it works really well with the same jeans and boots.

And this is cute too, with the loafer mules and my Everlane varsity cardigan.

See how the shorter sweaters in the thinner knits keep the overall look balanced?

Here’s me trying the look we photographed above… sometimes I think it’s nice to see the mirror selfie as well.

And then I tried a silky tank top with a leather jacket on top. I like this for date night!

Taking it more casual, this hooded sweater is cropped and boxy, which works with the jeans, and I added my white Vejas.

This look would be better if the jeans were an inch shorter, so I tried a cuff, and I also gave the sweater a front-tuck.

Here’s another casual look, with different sneakers and a sweatshirt that’s on the thinner side.


And un-cuffed…

And then I have a couple with the Goodthreads jeans.

I ordered two colors — the darker pair is the 28, and the lighter pair is the 29. The 29 is more comfortable, but the 28 fits, and if they bag out any, it might be the better choice. I still need to wear them around the house and see how they do.

This sweater (more sizes here) is on the chunkier side, but I happened to have it on already, so I tried it first with the darker wash jeans and loafer mules. I like it!

And here are a few more shots of the striped hoodie with the light wash Goodthreads jeans.

As an aside, this hoodie is AMAZING, you guys. Super soft inside and out, a nice substantial fabric — not super thick, but not thin either — and the fit is cute too. Very good quality for Amazon, and I’m definitely keeping it!

I love this look for casual weekend outdoor events in the springtime.

I realize I’m breaking my own rule here with a longer top, but because everything is light — the light grey/white top, light jeans, light shoes (and my winter-white skin, haha!) there is nothing to break up the look, and I think it works fine.

Shop the Post:

For the Pinners:

Showing you how to style straight crop jeans for winter with boots, mules, and sneakers. Lots of outfit ideas!

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photos: Alison Cornell