Experimenting with Chelsea Boots and Straight Leg Jeans

I promised you guys I’d play around with Chelsea boots and straight leg jeans, and I’m a pleaser, so here we are!

If you’ve hung around these here parts for very long, you know that I loooove my skinny jeans. I’m still a fan, and I will continue to wear them.


Some of the newer boot styles are not playing so well with my favorite skinnies. Case in point: the Chelsea boot.

Vince Henderson boots (size 8)

What is a Chelsea Boot?

If you’re not quite sure, Chelsea boots are close-fitting, ankle-high boots with an elastic side panel, and they’re worn by both men and women.

Vince Henderson boots (size 8)

They’re a classic style that has become very much on trend as of late, and they’re quite a change from the lower shaft, western-inspired styles we’ve seen over the past few years, often with a split shaft.

I picked up these beauties at the #NSale back in August when they were on a significant markdown.

They are absolutely gorgeous, practical (waterproof… holla!) and right on trend with the Chelsea boot silhouette on a lug sole.

But now that it’s finally chilly enough around here to wear them, they have created some annoying outfit problems. As in, they don’t look very good with my go-to skinny jeans. Hmph.

Last week, I tried to wear them with these Good American Good Legs jeans I’ve been wearing so much lately, but something about the pairing just seemed off.

sweater // jeans // boots

As I explained then, these booties have a tall, slim 5″ shaft, and the jeans seem to cut off at an awkward place.

Even though they’re skinny jeans, the leg opening of the jeans appears wider than the shaft of the boot, so it chops up the line of the leg, even though it’s all the same color.

Here’s a close-up of the side view — see how the hem of the jeans gets stuck between the heel tab and my leg, and then they fall over the front of the boot.

sweater // jeans // boots

I don’t know, maybe I’m over-thinking it. It doesn’t look terrible in these pictures, but when I’m looking at myself in the mirror, it’s all I see.

And I have the same issue with other Chelsea boots too, like these Marc Fisher Yale Chelsea boots.

I think these jeans actually look worse with these boots — I guess because they have a slightly lower shaft, and the line of the leg looks even more chopped up.

sweater // jeans // boots

As we discussed in the comments of that post, Chelsea boots seem to call for a different style of jean — one with a wider leg opening that allows the jeans to fall over the boots, or a crop style with a wider leg opening.

I styled the Vince Henderson boots with the rag & bone Dre slim boyfriend jeans (currently 40% off!) for a blog post back in August, and they seem to work well together when the jeans are cuffed to land right above the shaft of the boot.

sweater (XS) // tee // jeans // boots

I wish I’d tried these yesterday during my try-on sesh, to see how they looked in the mirror. I only have photos with a side-view from that post.

Of course, that will only work when the weather is mild. Once it gets colder, I’ll want to be able to wear socks, or at least wear the jeans over the boots, so I need to see how they look left un-cuffed.

So anyway! Yesterday, I set out to experiment with Chelsea boots and straight leg jeans.

Paige Cindy Straight Ankle Jeans + Vince Henderson Chelsea Boots

This is the Paige Cindy, and it has a 27″ inseam with a 14″ leg opening, for those who pay attention to measurements.

For comparison’s sake, the off-black Good American Good Legs skinnies shown above with these same boots have a 27 1/2″ inseam with a 10″ leg opening.

sweater // jeans // boots

Don’t get too distracted by the chewed hems on these jeans. They’re giving me all the Huck Finn vibes, and I’d prefer a plan raw hem or a more traditional sewn hem for these looks, but they are the best straight ankle jeans I have to play with.

(The Paige Cindy comes in a lot of other washes with different hems, if you like the cut of the jeans and not the wash. Unfortunately, none are on sale at the moment.)

Right off the bat, I feel like this pairing works really well. The jeans have a 27″ inseam, which is the perfect ankle length on my 5’5″ frame, and they fall nicely over the boots.

They’re long enough so that they don’t chop off the leg line, but short enough to expose some of the boot, which is on trend. And let’s face it, these boots are too gorgeous to cover up!

sweater // jeans // boots

I also think the heel on the boot helps my legs look longer and leaner, even though the jeans are on the shorter side.

And finally, this solves the frozen ankle issue we all face when we wear ankle jeans with lower shaft boots that expose part of the leg.

My only issue is, the color combination on this outfit is a little harsh. The black boots create a high contrast with the lighter wash jeans, but the darker top bookends the look, so I think it works okay. I probably would not like this look with a lighter top.

Paige Straight Ankle Jeans + Marc Fisher Yale Chelsea Boots

Next, I wanted to see how the exact same outfit worked out with the lower heeled, pointy-toe Marc Fisher Chelsea boots.

Again, the color contrast is a little harsh, but I feel like the jeans and boots look okay together. For some reason, I like the chunkier Vince boots better, though.

sweater // jeans // boots

Also, these boots have a slightly lower shaft than the Vince, and the back of my jeans gets caught in them when I move around.

But also note how the way these jeans are distressed, the hem is slightly shorter in the back than in the front. If they were cut evenly all around, this might not be an issue. Or perhaps a straight leg jean with a 28″ inseam would work better with these boots.

sweater (S) // jeans (28) // target=”_blank” rel=”nofollow noopener noreferrer”boots (8)

Mother Insider Crop + Vince Henderson Chelsea Boot

Another pair of straight leg jeans that I’ve been struggling to make work with the rest of my wardrobe is these jet black Mother Insider crop jeans.

Unfortunately, this exact style is only available at Shopbop, and sizes are limited. There are more Mother Insiders at Nordstrom and Bloomies, but most have a frayed hem.

These jeans have a 25″ inseam with a 14″ leg opening, so they’re a full 2 inches shorter than the Paige Cindy shown above.

sweater (S) // jeans (28) // boots (8)

These are a true crop rather than an ankle-length jean, and I feel like they have a slightly flared silhouette, whereas the Paige Cindy definitely falls straight.

For this reason, I find these harder to style, and I always feel like they’re cutting off my leg line in an awkward way.

I’ve styled them a few times for the blog, but I rarely end up wearing them in my real life. I try them and always end up reverting to my comfort zone — skinnies.

I do like how they work with these boots. Because they are both black, there is little to no contrast between the jeans and the boots, so even though the jeans are cropped and slightly flared, I still get a cohesive look on my lower two-thirds.

sweater (S) // jeans (28) // boots (8)

The other frustration that I’ve had with the back of the jeans getting stuck on the tab of the boots is eliminated with this pairing because of the flare. It just doesn’t seem to be an issue, even though the hem of the jeans barely covers the top of the boot.

I just wish I had thought to style this outfit a bit more — I think a front tuck and a belt would really improve the overall look.

For one thing, it would balance out my proportions a bit — with the shorter jeans, a shorter top works best. Plus, it’s all rather plain, and I think a belt would really take it up a notch.

Mother Insider Crop + Marc Fisher Yale Chelsea Boot

I also wanted to see these jeans with the Marc Fisher Yale, and this is just okay to me. I don’t know if it’s the pointy toe or the shiny leather or the lower heel or a combination of all three, but something looks off to me.

sweater (S) // jeans (28) // boots (8)

Maybe the jeans and the boots are okay, and it just needs a different top. I think an edgier look on top — perhaps a moto jacket over a graphic tee — would be better suited to these boots.

I was trying to cut down on the different variables, so I styled everything with this same top, but I should have played around a bit more with other options.

sweater (S) // jeans (28) // boots (8)

The rear view is where these lose me; and I apologize for my nasty iPhone screen. I didn’t realize how bad this was until I went to upload these pix. But this rear view looks really elf-like to me, with the pointy low-heeled boots poking out from under the crop flares. I’m not feeling it.

sweater (S) // jeans (28) // boots (8)

And yes, I should have done rear view shots of the other looks… I didn’t even think about it.

Mother Insider Crop + Aquatalia Tilly

Finally, just for the sake of argument, I decided to try this same look with my Aquatalia Tilly suede sock boots.

I picked up these boots on an end of season sale last winter, and I already knew I liked how they looked with these jeans, so I wanted to try them on to compare to the Chelsea boots above. Even though they’re sold out, I link them so you can see the details and specs.

sweater (S) // jeans (28) // boots

These booties are a classic style that’s hard to define. I usually call them sock booties because of the high, slim 7″ shaft. That makes them really easy to slip under jeans and pants of all different lengths; I can even wear them under my skinnies.

They’re also weather-proof, so they’re perfect for our messy Pennsylvania winters.

The classic styling works better with this top, and in this case, I actually thought to give it a front-tuck.

sweater (S) // jeans (28) // boots

I feel like this pairing works, although I still see that skinny shaft against the wider leg of the jeans, and it seems weird to me. Maybe my eye just needs to adjust to the look after wearing primarily skinnies for so long.

Yes, I realize they aren’t Chelsea boots, but comparing other styles helps me decide if I like the Chelsea boots with these jeans or if there’s a better option.

Mother Insider Crop + AGL Pointy Toe Flats

Before I quit, I wanted to try one more thing — the AGL pointy toe flats.

Of course, these aren’t boots at all, but I had a feeling I might like them with this top and jeans, and I would love to find a few ways to wear these jeans so I can get a lower cost per wear out of them.

sweater (S) // jeans (28) // flats

While I still prefer the silhouette of a skinny jean, I can appreciate that this outfit is modern and flattering.

The proportions are working, and if I add a belt, I think I have a look I’d be comfortable wearing out and about.

sweater (S) // jeans (28) // flats

Of course, that doesn’t solve my Chelsea boot dilemma, but at least it gives me another option with these jeans.

As for the Chelsea boots, I think they work best with the straight ankle jeans.

I’m excited to come up with some other outfits around that pairing, although now I want to get a pair of straight ankle jeans without that chewed up hem… Time to go shopping, ha!

It never ends, does it!?

I hope this was fun. I know I could have been more thorough and tried some other combinations, but I wanted to get this post up today. I’ll definitely keep playing around with Chelsea boots and straight leg jeans as I’m putting outfits together over the next few weeks.

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