Fall Trends to Try: Flare Jeans Now & Later

Happy Friday, friends, and cheers to the weekend! Today I’m teaming up with Cyndi Spivey to style another trend for now and later, and today we’re bring flares back! Although I’m cheating a bit, as mine are technically bootcut jeans.

When I asked on Instagram if people are into flares, 75% said no, so . . .  I’m not sure how many of you even want to see me style these pants, but we’re doing it anyway!

These are the AG Angel bootcut jeans, which I found at Nordstrom last spring, although my exact wash is only on Amazon now it’s the 17 Years Ceaseless Destructed. And there’s a pair in a very similar wash (a little less distressing) on sale at Shopbop the sale ends tonight, and the code is STOCKUP19.

I sized down to the 28, which is a bit snug in the waist, but I was afraid the 29 would be too big in the thighs.

These are obviously a very casual wash, so I decided to style a more casual look with them something I’d wear for running errands, to go to my one of daughter’s band performances, or to hang out with friends on the weekend.

The issue with bootcut jeans, of course, is that they require your shoes to have a very specific heel height.

I always get my bootcut jeans hemmed to wear with heels because I think they’re most flattering that way, so that made it even harder to create a casual look, but I found these Vince Camuto Gigietta booties in my closet, and I think they’re perfect.

(There are more sizes at VinceCamuto.com, by the way. Mine are Tortilla Suede, and I recommend sizing up half.)

The Western styling makes them more casual than most of my other booties certainly more casual than pumps or my peep-toe sandals and the pointy heel helps elongate the leg, which coupled with extra length of the bootcut jeans gives you legs for days!

These booties have a 3-3/4″ heel heel, which is the height of heel I brought with me when I had my jeans hemmed. A lot of my heels are in that 3-3/4″ 4″ range, so I knew I’d have some options.

This is a comfortable heel for me, but of course you can wear lower heels with bootcut jeans and flares . . . just be sure to have them hemmed accordingly.

FIT TIP: Ideally, your flares will be 1/4″ — 1/2″ off the ground, with shoes on.

To keep the look casual, I styled these jeans with a graphic tee.

I’ve purchased a few graphic tees lately, but this one is my favorite for its wider neckline and flattering fit, and it’s a nice quality slub cotton.

I also fell in love with the NYC skyline with the red embroidered Manhattan. Living in Philly, I end up in NYC a few times a year, and I love the energy and pace of the city, so I thought the tee was fitting.

For accessories, I wore this Lucky Brand bracelet, and I meant to bring these earrings.

I love Lucky Brand jewelry with my casual outfits, and the mixed metal look is very much on trend at the moment.

I carry all handbag styles, but a tote is always my favorite, and my taupe Everlane tote coordinates nicely with the booties they don’t match, but they go. #thankyoustacyandclinton

While I don’t typically hang around the house in 4″ heels, I like this elevated casual look for ball games, kid’s events, casual coffee dates, things like that.

To take my flares into winter, I basically just swapped out the tee for a sweater.

I also changed boots to a pair that’s darker and more conducive to wearing socks, although I’ll probably wear the Gigietta booties all winter, depending on the weather.

This camo sweater is from Anthropologie, and while it’s pricier than some, the quality is really outstanding, and I love the fit and feel.

Anthro does run sales from time to time; in fact, this sweater was on sale for a few days last week, so it’s one to watch if you like it and don’t want to pay full price. (Click the “Get Sale Alert” button below the picture in the shopping widget at the end of this post to receive an email when it goes on sale.)

This bag is an oldie but goodie, and it works in well with the polished but edgy vibe of this outfit.

The price seems to fluctuate (#amazonproblems) and I paid a lot less than it is currently going for, but even if I’d paid full price, the cost per wear would be mere pennies at this point.

And don’t be shocked, but I’m wearing a belt! I really like how it completes this look.

For many years you really didn’t see a lot of women wearing belts, and now they’re everywhere. Of course, the logo belts à la Gucci are the trend du jour, but I went for one that’s a more subtle.

This O ring belt by Rebecca Minkoff is a glossy but very soft leather, and for size reference, I needed the large.

My booties are Club Monaco. I saw them on another blogger a couple of years ago and stalked them until they went on sale. They’re gorgeous, but they don’t seem to have a similar style this season, so I hunted down a few other options.

These are similar, but with a lower heel for those who want that; and these are a good option for a more budget-conscious pair. I also like this pair, and this pair looks amazing if you prefer leather. (The last two are on sale at Shopbop through end of day.)

The only other thing I’d add to this “later” outfit is my black leather jacket. Besides the extra warmth, it would make a great completer piece to this simple look.

I’m excited to see flares and bootcut jeans becoming more popular again, although I’ve yet to see the ladies in my neck of the woods wearing them. I’m still very much in skinny jean country, but I don’t see trends taking off here as early as they do in more urban areas.

I’m curious if you’re seeing a resurgence of flares and bootcut jeans where you live. I do love my skinnies, but it’s nice to have other options.

How about you? Are you ready to rock the flares?

Outfit Details:

AG Angel Bootcuts (on sale at Shopbop) // NYC tee // taupe booties // taupe tote // camo sweater // similar black sock booties (more below) // black satchel // O-ring belt // sunnies c/o Maui Jim

Be sure to visit Cyndi and see how she’s styling flares for now and later!

Did you like this post? 

Subscribe to get email updates! In addition to my most recent blog posts, you’ll receive exclusive newsletter content like special sales, my newest favorite finds, and an occasional peek behind the scenes — all delivered right to your inbox. PLUS you’ll be automatically entered for a chance to win a $100 gift card each month!

This post contains affiliate links. When you shop through my links, it helps support my business (at no additional cost to you) so thank you!

photos: Alison Cornell