Revisiting Kick Flares for Fall

There were so many good comments on the post about the kick flares for fall that I decided to write a follow-up, rather than try to reply to everyone.

For anyone just tuning in, here’s the outfit in question:

I happened to be shooting with my photographer, Alison, the day that post went live, and she was shocked to hear that most of you didn’t care for the outfit. She loved it and thought it really worked. (She also loved the gritty backdrop, for what it’s worth. 😉 That was on purpose.)

Her take on it was, this is supposed to be a relaxed, casual, almost sloppy look. Think casual-cool and laid-back (a messy bun would have probably helped…)

Now, keep in mind, she’s at least 10 years younger than I am, and definitely has a casual-cool personal style, but she thinks people just need time for their eye to adjust to a new silhouette.

I think she’s right to a point, but I also don’t think this outfit works for me — for the reasons many of you stated in the comments. The casual-cool, almost sloppy vibe doesn’t really jibe with my style aesthetic, and then there’s the bulky sweater with horizontal stripes that doesn’t do much for my short-waisted, larger busted figure.

So yeah, that’s why I felt like the outfit worked in theory, but it didn’t translate the way I wanted it to when I put it on.

The comments on the post were interesting, and I thought so many of you made valid points. A few of you actually liked the look, some of you hate kick flares altogether and think I should burn them (ha!), but most thought the pieces were all fine on their own — just not together.

Yes, these jeans are very casual due to the wash, the extra wide flare, and the raw hem; but I’m not ready to throw the baby out with the bathwater just yet, so I decided to try a few more top and shoe combos with them.

I also tried some outfits with two other pairs of crop flares, but before I share the new outfits I put together, I will address a question I’ve had a few times, and one I’m sure many of you are thinking:

Why try so hard? Maybe this trend is just not worth it.

I hear you, and I get it, but who remembers when skinny jeans were new? And the uproar . . . Oh, yes. There was an uproar, my friends!

People fought tooth and nail to hold onto their bootcuts, and many of us struggled with the new silhouette before we finally embraced it. I know I did!

(I am speaking in general terms here. Yes, I know not everyone embraced the skinny jean, but it definitely became the style du jour, and it has had a long reign in this ever-changing world of fast fashion.)

We transitioned slowly, first wearing straight leg jeans, then cigarette leg jeans, and finally legging jeans.

But the tops in our closets didn’t work with the new skinny jean trend, and neither did our shoes. We had to start thinking differently about how we put outfits together… What tops go with this new silhouette? Which length of jean works best with my shoes? And, ohmyword… what about ankle boots???

My blog post about how to wear ankle boots is was originally written back in 2015 or 16 (I’m not sure when because I update and republish it almost every year), and it was and still is the most highly trafficked post on my blog every fall and winter.

It was born because I was trying my darnedest to figure out how to pair skinny jeans and ankle boots. Oh, the angst . . . I remember it well!

Now that styling skinny jeans finally seems like second nature, they want me to start wearing straight leg jeans and flares!

And suddenly my tops don’t quite work, and I’m trying to figure out the shoe situation, and here we are again.

But that’s fashion, folks. And this is a fashion blog. So, to keep it relevant, I make it my job to figure out how to wear the current styles, and I don’t think this silhouette is going anywhere.

Granted, we should wear what looks best on us, but I don’t think ignoring trends is the way to do that. Oftentimes what seems trendy one day will seem mainstream in a few months.

Of course some trends come and go, but pant silhouettes have a way of evolving, and I predict that we will get used to this silhouette. Let’s revisit this post next fall, shall we? We may see it very differently.

So yes, I’m still experimenting with kick flares because I’m curious to see if I can make them work for me, and I’m bringing you along for the ride.

That doesn’t mean I will keep this exact pair of jeans, but the style in general is one I’m not giving up on just yet.

And now, with that lengthy preamble out of the way, I present to you . . .

Kick Flares: Take Two

I’m going to start with restyling the BlankNYC Varick kick flares. Yes, the wash and the cut hems make these very casual and almost sloppy, but that’s actually what drew me to them. I like that look to a point, but the casual/sloppy vibe isn’t the easiest look to pull off as we get older, so it really has to work with your personal style aesthetic or it can look try-hard.

With the chunky sweater and mules in Tuesday’s post, that outfit ventured into try-hard territory. As I said in that post, I couldn’t imagine actually wearing that outfit anywhere. That’s usually my gut-check signal that a look isn’t for me.

That said, I do work at home and dress pretty casually most of the time, and I love my ripped jeans, so I think I can wear these jeans if I keep them uber casual.

In that vein, many of you suggested wearing them with a graphic tee and sneakers. Take a look.

Much better, right? I can actually imagine wearing this outfit somewhere.

I tried a few more variations with these jeans before moving on to a different pair . . .

While the white sneakers play nicely with the lettering on the tee, they still contrast with the dark outfit and draw a lot of attention to my feet, so I tried a darker shoe.

I like this look, but I think a more casual dark sneaker would be better. Unfortunately I don’t happen to have one at the moment to show you. #holeinmycloset

So I went the other direction and tried a plain black tee with these leopard slip-on sneakers because it’s a bit more polished and makes more sense with the shoes, and I think this works.

I’d wear this to run errands or to meet up with a friend for coffee.

Then I tried these snake print mules. They have a bit of a wedge, which some suggested might help with the kick flares, and they’re okay . . . but I like the sneakers better, I think.

Then I thought perhaps a grey tee would work better with the white sneakers, so I tried that. I like this but I think the lower vamp on the snake print sneakers is more flattering because it shows more skin. Did anyone else notice that?

So yeah, all in all, I like the graphic tee and sneaker combos. Are they polished and sophisticated?

No, but that’s not the point.

This is just a fun, playful look that can be appropriate for certain casual situations . . . hanging out with friends on the weekends, working at home during the day, running errands, a fair or music festival on the weekend, a ball game, or a kid’s band performance in the football stadium. (I’m a #bandmom, can’t you tell?)

So What About Booties?

A lot of people said they prefer kick flares with booties. The issue with booties is, you need to find the right silhouette and right shaft height to work with the jeans. You don’t want too much skin showing, but you don’t want the jeans getting caught on the shaft of the boot either.

I think these Sofft booties are about the right style/height, but I don’t love them with the graphic tee. I think they need a sweater on top.

So I tried a different top — one that’s still casual, but long sleeved for cooler weather.

This thermal is more fitted than the striped Madewell sweater and has a more fitted silhouette, but it doesn’t quite work with the jeans because they both flare out.

A better option is a top or sweater with a more traditional silhouette, and if it’s too long, you can front tuck it . . . like in the case of this camo sweater.

I wish I’d tried this with the grey booties, because I actually think it would work, but I only have a picture of this combo with sock booties.

Sock booties are always my answer to the question: “But what do I wear with cropped jeans in the wintertime?”

I think this look has potential, but these jeans are probably too casual for these booties. The grey ones would probably look better style-wise and color-wise, and I also think the jeans should be an inch longer to work with these sock booties.

AG Jodi Try-Ons

So let’s try some other kick flares and see if they work any better.

I picked up these AG Jodi crop flares when I saw them on sale at Bloomies because AG never steers me wrong . . . or so I thought.

First of all, they run suuuuper small, despite what the website indicates. I am wearing the 29 and I could barely button them. I definitely need a 30, and I often wear 28 in AG, so I don’t know what gives there.

I’m also not loving the contrast in the wash — the distressing is too severe for the dark wash, in my opinion; but I tried them since I had them.

To compare, the AG Jodi has a 9.25″ rise, 26″ inseam, and 16″ leg opening. The BlankNYC Varick (styled above) has 8″ rise, 25″ inseam, and 16″ leg opening.

First up, I tried the AG Jodi crop flares with a grey tee and white sneaks. It’s fine, but I like the Varick better, mainly because I like the wash better.

Next, I swapped out the sneakers for the snake print mules to elevate the look a bit, but I’m meh on this one.

Let’s try the sock booties and a sweater. I like this silhouette better, but the distressing on the jeans is still distracting to me.

That said, note how the extra inch in the inseam looks so much better with these booties!

And one more option… a less chunky sweater with a slightly shorter length. This actually works really well, except for that awful wash on the jeans. If they were more uniform with the darker wash, I think I’d like this outfit.

Mother Insider Try-Ons

Okay, last pair! I decided to try the whole round of outfits again with these Mother Insiders. These have a 9.75″ rise, 26″ inseam, and 15.5″ leg opening, but they seem slimmer than the two above.

These also have a lighter wash, so I think they look best paired with lighter shoes and tops. They’d definitely work with the grey tee but I tried them with this navy one for variety’s sake.

I think this is a pleasing blend of styles, fit, and colors; and I like how the jeans don’t seem as wide at the bottom as the BlankNYC pair. They don’t feel like they will be as much “work” to style . . . but let’s see. One outfit does not a new pair of jeans justify! 😂

It was also suggested that I throw a cardigan on top, and I like this okay, but I think it makes me look bigger on top — and that along with the width on the bottom isn’t as flattering as the tee worn alone.

Next, I kept the sneakers and tried a sweater. Last winter I got into the cashmere sweater with jeans and sneakers look. I like the juxtaposition of luxe and casual.

I dunno… what do you think? I think I’d like this better with my navy hooded sweater, but I didn’t think to try it. I’m not loving the rust with the white sneakers.

Next, I swapped out the sneakers for the snake print mules to elevate the look a bit. Since they’re a lighter print, they don’t contrast too much against the light denim, extending the line of the leg. Plus the small heel helps too, but I still can’t say I love this look.

For comparison’s sake, I asked myself which of my go-to jeans would I probably reach for if I were going to wear this sweater and mules together right now . . . and I grabbed the Rag & Bone Cate — dark wash skinnies with a raw hem.

So much better, right??? Maybe it’s partly the darker wash, but I think the extra length of the jeans, and the slimmer silhouette clearly creates a more pleasing balance.

And to take it one step further, I swapped out the mules (which I have not yet committed to keeping) for my beloved snake print booties that I’ve worn several times already, including last night and this morning.

Now we have an outfit I want to go put on right now and wear somewhere. But… I’m persistent.

Thinking a lighter color sweater might work better with the Mother jeans and snake mules, I tried on this ivory link stitch sweater from Everlane.

It’s okay, but I decided I just don’t love these mules with these jeans. Everyone keeps saying booties is the way to go with cropped flares, and they’re more practical as it gets colder, so I tried the Lucky Brand suede wedge booties in sesame.

Tell me what you think. The colors definitely work, and you can see just about an inch of skin between the booties and the jeans, which supposedly works, but I don’t love it.

I told you I’m persistent… Next I tried grey booties with a higher shaft. These aren’t as snug to the ankle as a sock bootie, but they have a streamlined silhouette and a higher shaft so there is no skin showing between the jeans and booties. I could even wear socks with these for warmth.

What say you? I think this is the best one yet… except for the navy tee and white sneakers above. I like that outfit too.

Since I like the boot and jeans combo, I tried another top — this J.Crew rollneck cotton sweater. It’s too long with cropped jeans, though; now I’m cut in half.

But that is the problem with new denim silhouettes. Suddenly tops you thought were effortless to style don’t quite work, and this is why we’re seeing so many shorter tops right now.

See how much better the AG Prima look with this sweater and booties?

I did try one more thing — cuffing the AG Primas and front-tucking the sweater.

I’m not really a fan of front tucking sweaters, but it seems to be what everyone is doing, especially with the longer ones. And I noticed they had this sweater front-tucked on the website.

So yeah, it’s a work in progress! I’m not sold on kick flares just yet, but I like a few of these looks, so maybe I’ll venture out wearing a pair one of these days.

Meanwhile I’m going to keep trying different styles and watching how other influencers wear them, and when I’m in areas that are a little more fashion-forward than my area of the ‘burbs, I’ll be looking around to see which silhouettes are taking hold in the mainstream.

I will keep you posted, and feel free to let me know if you have suggestions on improving any of these outfits. I’m open!

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