How to Wear High-Rise Flares: 3 Ways to Try



When we visited Philly, Zack and I were in shopping heaven.  There were stores GALORE . . . H&M, Zara, Forever 21, my usual spots to check out.  Shana brought me into Madewell, a store I had never actually been in, to try on jeans.  I knew their jeans looked great on Shana, but I had low expectations for myself, because . . . BOOTY.  Typically, if something looks awesome on Shana, it won’t necessarily look great on me.  (*Although now we’re finding more and more options that actually work for both of us.)

I was super pleasantly surprised by these jeans, because they are awesome.  High-rise to suck in and shape the pooch, flared to make your legs look looong and black to be as slimming as jeans can be.  Here are three ways I’m wearing them:

1. Blouse Tucked In 


With a thinner and/or shorter shirt, tucking in is always a great option with high-rise flares.  It accentuates your waist and other ASSets that you may or may not have.  Ahem.




Outfit Details

Madewell ‘Flea Market’ Flares

H&M Chiffon Blouse

2. Blouse Tied Up


I wanted to still show off the higher rise of the jeans but I didn’t want to always have to tuck.  Sometimes you just want a different option . . . in this case, a small knot works great.  I’m definitely not talking about a Daisy Duke under-the-boob knot and I definitely don’t want to be showing off any belly.  However, a well-placed knot gives you that tucked-in look without having to deal with all that fabric actually tucked into your pants.  black-high-rise-flares-6



Outfit Details

Madewell ‘Flea Market’ Flares

Express Portofino Shirt (Now available in Sleeveless, Slim-Fit and Silky Crepe)

3. With a Tunic, Untucked

I will always love a tunic length.  Sometimes you just don’t want to be showing off any part of your midsection (Thanksgiving, anyone?) but that doesn’t mean you have to forgo the flares.  With a longer shirt you still get the lengthening illusion of the black flares but don’t have to worry about how much food you eat (or beer you drink!).  black-high-rise-flares-11


Outfit Details

Madewell ‘Flea Market’ Flare Jeans

Express Portofino Tunic (I’m loving the longer length and also wear them with leggings and over-the-knee boots!)


High-rise, black flares are going to be a big part of our holiday style guide….so more to come!




  1. I’ve been wearing Curvy fit flares from Old Navy. I know, Old Navy, but I am so tempted by all the tall sizes (long arms and long legs) there I can’t see to stop putting in orders “just to try it on” They fit my booty so well and are slim through the leg and a nice flair. I’m not sure if they are true high rise, they hit a bit below my belly button. I’ve worn them for 5 days now and they are not bagging at all, it’ll be interesting to see how they wash. I had to size down quite a bit (I ordered a 10 and 8 but then had to return both and get a 6). They are a light denim and have worn them a tunic length “boyfriend” red flannel, a tissuey loose t-shirt tucked in at the front and a cozy turtle neck sweater. My only minor complaint is the belt loops are a bit big, they can be lumpy under a fitted shirt if not tucked in. Not bad for $25.

  2. I love the looks here! I am so ready to buy my pair to high rise flares the second this baby is out and the postpartum bloat is down! The high rise will do wonders for the ever present pouch at the beginning! I love doing a full or half tuck, but I think at the begining I will be rocking more of the full out look – hello, #2 baby flab! Great post!


  3. Scotti, your bod is pretty stinking incredible. These exact flares were in my Madewell shopping cart but I just found out I’m pregnant with my fifth baby so they will just have to stay there and never sell out for a solid year until I can get back to them. I just bought that Free People tunic all you bitches are wearing lately so hopefully that will work for Thanksgiving. Have a great holiday! Send warm cuddles to Shana for me (so long as she’s not in those stooooopid jeans I hate, ha!) xoxo!

  4. Hm. I’m probably in the minority, but I’m not the biggest fan of what these jeans are doing to your (fab!) body. They seem to be adding weight to your midsection and aren’t hugging your curves enough. I think a thinner through the leg option may work better? Maybe a less heavy denim material option? something here seems bulky. you still look lovely & I do like the style options, I’ve just seen you look more amazing in other denim cuts. Just my humble opinion xoxo

    • I thought the same thing Cristina, those jeans seem to baggy in the leg…I like flares for the leg-slimming effect, and these seem too big in that area. I am loving my Express mid-rise flares (I can’t do a high rise because there are for real only two inches between bra line & waist). I love the styling suggestions.

    • Oh no! Well thank you for the nice way you phrased that! 🙂 You’re right, they are more “structured” than some other jeans and aren’t as tight and stretchy as some. I’m hoping it’s not the Halloween candy . . . LOL

      • I gotta disagree with Cristina. I think you look great. The high rise makes you look very Marilyn. Defines your waist, accentuates your curves. It’s a beautiful, feminine look. Go flaunt it and make the hubs drool.

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