What to wear with flared jeans

Back when I was in Paris (it feels like ages ago although it was only last month), I noticed all of the coolest women were wearing flared-leg jeans. At first, I thought, "Been there, done that," but Parisians have that effortlessly chic way of wearing anything that just convinces you to just go for it. At the ripe age of 42, I feel like I've lived through at least two rounds of flared jeans in my lifetime, but it appears they're on the verge of another comeback. And while I normally take a pass on trends I've already endured, I'll generally make an exception for denim. Thankfully I held on to a pair of flares from about 12 years ago, the last time they were in fashion, and I'm glad I did, because here we are. So here's how to style flared denim and not look like your 18-year-old self.


These jeans can probably be considered vintage—they're Current/Elliott from when the founders were still designing the line, which makes them at least 12 years old, possibly more. They've ended up in my giveaway pile multiple times over the years, but I've ended up saving them repeatedly because they fit like a damn miracle. They have a high rise, which, at the time, was virtually unheard of, but as we know now, is way more flattering than a low rise, particularly if you're a woman of a certain age with a midsection. The utility pockets in front help shape your thighs, which is critically important with a flared silhouette—if you are of ample thigh, the flare can often emphasize that in a not-so-flattering way. As tempting as it may be, you also don't want a pair that's too stretchy (or too light-wash, for that matter)—you want a little stiffness in the denim to hold the shape. If done right, a good pair of flares can give you mile-long legs, and I feel pretty good about what these do for mine. If you can find a pair of these on eBay, you're my hero, but if not, I've linked some very similar styles below.



So, in case you haven't noticed, I'm wearing a Canadian tuxedo, and yes, I'm also wearing the same Madewell chambray shirt I wore last week. This entire look was inspired by the Celine 2020 spring runway; the key to wearing denim on denim is to vary your washes. The shirt is lighter, the jeans are darker, and so it works. As I've noted many times, Madewell makes the best chambray shirts, and if you can get one on sale, you are the luckiest lady around. They run true to size, if a bit generous; I'm in my usual size small.



As is generally the case when you throw on a blazer, it really pulls the look together. Without one here, the denim-on-denim could go into hokey territory; with it, the whole thing just feels more intentional. As I've mentioned recently, I'm leaning more into navy lately, as I feel like it's a little softer on my aging skin than harsh black. (Of course, now that I've said that, you'll see me in nothing but black.) I think Theory makes some of the best blazers around, and they're totally worth the investment. I've had this one for years, I take it everywhere, and it looks just as good as when I bought it. They run true to size (I'm in a 6).



This look is obviously all about the denim, but the accessories give it a little personality. I actually have to wear a belt with these jeans because their one flaw is that the waistband has snaps, so if I bend over or sit down too quickly (or eat too much), they unsnap themselves like that. It's embarrassing and also a little funny. The jeans are a little on the longer side, so normally I wear a platform or big heel with them, but when I saw that Celine styled theirs with a sneaker, I decided to try it. Also, I've pretty much been wearing sneakers nonstop, so it's not like I was going to put on real shoes or anything. Wearing high-waisted jeans was enough of an effort! ;)



11 comments

Laura B said...

Love your denim look! How perfect you've kept those jeans after so many years. They do fit you really well and it is perfect because they are now back in style!

eva @StyleMyThrift said...

i am loving the flared jeans! i just made myself a pair from a thrifted pair of jeans..but i made mine cropped...i;m 5' 4" so long flare jeans don't look right on me...but you pulled it off!
i just made myself a Puffy Sleeved Blouse from a long sleevless dress...I'd be honored to have your opinion!
can i post link here? or email it to you?
thanks!
xo eva

the 4 M's said...

I really should try a denim on denim look. I do find it interesting how styles cycle back.
www.chezmireillefashiontravelmom.com

Lucy said...

Flare jeans are my absolute faves!! And yes- I totally agree about them giving mile long legs lol!!

stylesplash@live.co.uk said...

I love a jeans and blazer combination! The different shades of blue look great together. I'm going to dig out some of my old flared jeans and give them a try! Thanks for linking up!

Emma xxx
www.style-splash.com

Shelbee on the Edge said...

Cheryl, I adore this outfit! I love the flared jeans and I am glad that are making a comeback! They are so cute with your sneakers and blazer. Thanks for linking up with me!

Shelbee
www.shelbeeontheedge.com

Jessica Jannenga said...


Hi Cheryl
What goes around comes around, right? Those are some great flared jeans on you! I actually scored some Brand lovestory flares for 25 bucks this year thrifting. Love it with the blazer and you know I love that leather bag!
You look great!
take care,
jess xx
www.elegantlydressedandstylish.com

idil said...

Love the way you carried the denim and the blazer. So effortlessly chic! As a firm lover of flare jeans myself, I am thrilled to see them coming back. Great shots!

Love,
i.b. | http://soundslikeidil.blogspot.com

Just Live Joy said...

I'm loving this look so much! Those jeans are fabulous on you!!
https://justlivejoy.com/traditional-style-office-studio-mcgee-art/

mummabstylish said...

These really do look great on you, unfortunately they don't suit my figure. Thank you for sharing on the #linkup Jacqui x

Mica said...

First up, you're 42? Oh my goodness I thought you were a decade younger!!!

Secondly, I really love the double denim. I tried my flares on the other day - I kept one pair from my uni days - to find out that two kids later there was no chance of ever fitting back into them, ha! They are in the donate bag for whenever the opshops open up again for accepting donations.

Thanks so much for joining the #WeekdayWearLinkup! The new link up is live on my blog now, I'd love you to join again.

Hope you had a wonderful weekend :)

Away From Blue