Fall/Winter Fashion

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!

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photos: Alison Cornell

Join the Conversation

85 thoughts on “Fall Trends to Try: Flare Jeans Now & Later

  1. Hello

    Bootcut all the way for me please.

    I unfortunately have hips which rather dictates the need for boot cuts or flares. Sadly under no circumstances can I wear skinny jeans – which kind of makes jean shopping rather tricky here in the UK as stores here seem rather reluctant to relinquish their skinny jeans.

    I think you look great in bootcut jeans.

  2. When I responded to the Instagram poll, I was thinking “kick flares” of which I am not a fan. However, if “flares” means boot cut, I say YES. These are so cute on you. A boot cut, or modified boot cut, is kind of universally becoming I think. However, I think it looks better in fall/winter. Todays looks are perfect! Thanks for sharing them!

  3. I love a good pair of bootcut jeans. I prefer the dark wash and black ones. I find they make us look taller & thinner. A win/win!  I don’t wear them as much as skinnies but still have them in my wardrobe for a change from skinnies. I’ve bought a few pairs of straight leg jeans as they seem to be trending. Now to get used to a change. 😜 
    I love your Camo sweater. It has cooler colours than most. Might be one to stalk! 
    I always wear a belt with jeans. I feel it finishes the look. I sometimes pick my shoes & purse after I pick my belt. Lol 

  4. I love these looks, especially the sweater and belt. I’m to the point that I really hope “style” will embrace that we all look good in different things and we don’t want to have to go buy all different tops and shoes to make things work when jeans styles change over. I’d rather buy new clothes because I want to, not because I have to. I think skinny, straight, and bootcut/flares all look current just now, and hope they all remain an option.

  5. I have been wearing the flared jeans  a long time.  I never gave them up.  Well for 2 + years I had to because if a foot  injury bug now I m beginning to wear some boots again I can bring out the flares.  I’m a 60 s child you know.   Loved the whole look.    Thanks for showing us your style.  I loved how you styled them.  Looks so cute on you 

  6. LOVE bootcut jeans. They look better on most people than skinny jeans do. Took me forever to love skinny jeans (which I do now). That being said, I’m reluctant to pull out those bootcuts because most of the population has not re-embraced them quite yet, so I feel a little too retro wearing them. Hopefully, all will soon accept fully both skinny and bootcut.

  7. Love both looks on today’s post! You look amazing! I am noticing from looking at photos on line and in magazines that boot cut jeans actually make people look slimmer than do skinny jeans. Maybe it is bc more width at the bottom balances what is on top? Not sure…..but after being long devoted to skinnies, I am realizing that I need to embrace the bootcut style!

  8. I don’t think I’ve seen any bootcut or flares around where I live which is a mid size city in the south. I only see skinny jeans and straight. I don’t really care for bootcut but I do like the cropped straight trend and the cigarette jeans you shared recently. Thank you for all the helpful advice and tips. I truly appreciate the help with figuring out what to wear.

  9. I think flares and bootcut jeans look MUCH better on most women. I wear them almost exclusively. You look great in them! I would love to see more posts including these flattering cuts!

  10. Love the flare jeans on you. Been waiting for bootcuts to make a comeback. They are really my favorite look and find them to be very comfortable.

  11. I really like the flares so I’m glad they are back in style.  Find they create a balanced and pulled together look. 
    I know I’ve told you before, but think you look best in flares.😊

  12. I finally found a pair of flare jeans I can wear with my purple cowboy boots. Can’t wait for it to get cooler in Arizona.

  13. I love flares and bootcut jeans! You look so great!! They are better for cooler weather because your ankles are covered. 😉

  14. Can you tell me what size you are wearing in the NYC graphic tee? I just love it and the reviews were mixed on the sizing. 

  15. I don’t care what your poll said, I am so glad that you styled the bootcut jeans anyway. I love bootcut jeans and they look way better on my pear shape than skinnies. Lol Would definitely love to see more. 

  16. I love flare jeans! So glad to see you styling them Jo-Lynne. I just purchased some from my recent Stitch Fix and I love them. Always have loved wearing them with heels. Whether they are on trend or not I continue to like them.

  17. I love this post! I’m very much a bootcut/flares girl (the skinny jean season for the past few years has been hell for me) so I’m excited to see this trend coming back. Please feature more outfits with flares/bootcut jeans. I love that sweater and definitely want to buy it…when it goes on sale!

  18. I know you think skinny jeans are life, but you always look AMAZING in boot cut jeans! As others have said, they are so much more flattering on most than skinnies. I hope you will continue to style these jeans. 

  19. I’m so glad that bootcut and flares are back in style. I lost 20 lbs recently and am wearing one size smaller in jeans and pants. I hit up my stash of smaller sizes and realized that the pants and jeans I saved are all flares. While I still love my skinny/ankle jeans and pants, I’m excited that my wardrobe has some versatility. What’s old is new again!

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