I can’t believe I have been a stylist long enough (16 years) that a trend has gone away and come back.  That’s right, I’m talking about bootcut jeans.  They’re baaaack.  I wouldn’t say they are back in a big way, don’t go pitching your skinny jeans into the donate pile just yet.  I call seasons like this, where a new trend is emerging, a disruptor season because everyone sort of scrambles a bit to make sense of what it means for their wardrobes.  I vividly remember when skinny jeans came onto the scene, there was all this confusion because there was a fundamental shift in the types of coordinating pieces one would need to make them work; for example, longer tops and tunics vs. shorter more shaped tops.

It’s also important to keep in mind that when a trend recycles you’re at a different stage of life.  The last time bootcut jeans were in I was in my late 20’s and early 30’s.  Now I am 44.  The likelihood that I will be wearing bootcut jeans the way I did back then in slim.  So despite the fact that many can remember a time when bootcut jeans were in style, we’re going to be introduced to them in a new way simply because we’re at a different stage of life.

The last thing to remember is that trends seldom come back exactly as they did the first time.  Trends don’t circle back, they spiral back, mildly touching on what they once were.  Back when bootcut jeans were all the rage so were extremely low cut rises.  With rises on the rise (no pun intended), I wonder if we’ll be able to dust off our jeans of a decade ago and not look out of place, that is if anyone still has them in storage.

Five Ways to Wear Bootcut Jeans

Now you may be thinking, “alleluia, good ridden skinny jeans, give me my bootcut jeans!” It is important to remember, however, bootcut jeans do come with their own dressing issues, many of which you probably have forgotten about.  The first is the size of the flare.  While bootcut jeans do have a counterbalancing effect, meaning that the flare can minimize the look of wider hips and thighs, too much flare can create an overemphasized curve and can make some women look hippy.  If you are bottom heavy like me, look for more minimal flares and keep in mind that a little flare goes a long way.  If you want to check how flared a pair of bootcut jeans are before trying them on, fold the hem of the jeans back to the knee and calculate how many inches wider the hem is from the width of the knee.  The greater the difference the wider the flare.

The next thing you probably long forgot about is how difficult bootcut jeans can be to hem.  Back when the bootcut trend was in, it wasn’t uncommon for women to have multiple pairs at varying lengths so they could wear their jeans with flats and heels.  Remember when you would try to wear the bootcut jeans you wore with your heels with your flats?  How many of you had frayed hems on your jeans because they dragged on the floor?

The third issue that arose with bootcut jeans was wearing them with flats.  Again, if you were too curvy on the bottom, heels always looked better with bootcut jeans because the leg lengthening look of heels optically caused the hips and thighs to look slimmer (anytime you elongate a part of the body you make it look slimmer at the same time.)  How many of you tried on bootcut pants or jeans and stood on your toes in the dressing room simply to make your legs look longer and leaner?  Yes, bootcut jeans seemed like the answer for all curvy gals, but they were riddled with their own issues.  Too much pooling of fabric from the bootcut flare can drag the eyes downward, overemphasizing large legs or bottom heavy body shapes.

Finally, the eyes take time to adjust to new things.  Part of how a new trend disrupts is just by looking different.  Have you ever watched an old television show that you loved ten or 20 years ago only to watch it again in present day and notice things about the clothes people wore on the show that you didn’t notice the first time?  What once looked normal to you, when watched in present day, looks awkward or silly. The reason for this is because the first time you saw the tv show your eyes were used to seeing everyone dressed the way the characters dressed.  Years later, however, your eyes had long gotten used to seeing new trends as normal and what once looked normal a decade ago now looks out of place.

As bootcut jeans make a comeback, I thought I would put together five different looks that are updated for today’s trends so you can embrace them again in an updated way.  I am using this pair from 7 For All Mankind.  Be sure to shop for additional styles at the end of this post.

Outfit #1

bootcut jeans

This first look is a chic and elegant weekend outfit for early fall.  I styled the bootcut jeans with a fitted white button down shirt from Theory that I layered under a Barefoot Dreams Ultra Lite poncho in taupe.  Finishing the look, I added these weatherproof booties in brick from Aquatalia, a brown croc embossed bag from Trademark and layering necklace from Stella & Dot.

Outfit #2

bootcut jeans

Next up, a professional denim look that can be worn in a business casual environment.  Styled properly, I quite like bootcut jeans in the office.  Often they can look much more professional than skinny ankle jeans.  I gave this outfit a work appropriate look using a navy blazer from Veronica Beard that I layered over a simple grey knit top from Majestic Filatures.  I finished the outfit with orange pumps from Charles by Charles David, a plaid scarf from Shiraleah Ripley, grey bag from Botkier and gold disc drop earrings from Kenneth Jay Lane.

Outfit #3

bootcut jeans

This more casual bootcut jeans look is a reminder that you don’t necessarily need to ditch your longer tops and tunics, but what you might find yourself craving is a bit more shape through the waist of these tops simply to create balance.  I styled these jeans with a plaid shirt from Rails and popped the look with bright red Sam Edelman flats.  The look is finished with a charcoal grey scarf from Chan Luu, black drop earrings from Kendra Scott and grey bag from Rebecca Minkoff.

Outfit #4

bootcut jeans

This next outfit is a business casual or dressy weekend look.  The pieces are simple, a sleeveless top in ivory from Nic + Zoe and a grey cardigan from Eileen Fisher.  The accessories add some interest to the look.  I added these tweed pumps in shade of plum and purple from Louise et Cie, a mauve crossbody bag from Kate Spade and statement necklace from Bauble Bar.  With a neutral base outfit such as this, you can introduce just about any accessories you wish to make this outfit look complete.

Outfit #5

bootcut jeans

This last rich look is perfect for the weekend.  I styled the bootcut jeans with a forest green wrap sweater that I layered over a brick colored tank.  The outfit is finished with a printed scarf from Tory Burch, cognac booties from SARTO Franco Sarto, rust bucket bag from Madewell and Kendra Scott earrings.

Shop for bootcut jeans