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How to Wear Bootcut Jeans

Bootcut jeans are flattering on all body types, are easy to dress up, and continue to be on trend as we slide into 2024.

There are just a few tips to follow as you style bootcut jeans.

First, and hands down the most important, the length must be correct.

So figure out the shoe you are wearing and make sure the hem of the jean slightly puddles on the top of your shoe. The longer you can wear these, the longer the line of your leg.

When bootcuts are too short, you look like you are wearing “floods,” and your outfit will be off balance.

If you need a hem be sure to ask your seamstress or tailor to keep the original hem.

Second, the kind of shoes you wear is important too. These look best with strappy heels or pumps, a wide range of boots from Chelsea boots to classic ankle boots, or a loafer with a block heel.

You want a little height to help the leg line hang correctly.

Skip flats, and don’t wear your sneakers no matter what the fashion gods tell you.

Maybe it’s the 90s girl in me, but sneakers and bootcut jeans give me Delia’s Catalog flashbacks.

Finally, don’t wear oversized or extra-long tops with your bootcut jeans.

Generally speaking, the combination creates too much fabric that will overwhelm most frames.

I’m 5’10, and it’s even too much for me.

Our Favorite Bootcut Jeans

Before we learn how to wear bootcut jeans, let’s discuss some of our favorites.

First, I like the Madewell Skinny Flare Jeans in Elevere Wash, available in sizes 23 – 33 in regular, petite, and tall sizes (I don’t usually need tall sizes, but I took them here so I could wear heels.)

These are high-rise with tons of stretch.

Plus size? I like their dark wash option here or this one.

If Talbots is more your speed, give their Barely Bootcut style a try in missy and petite here and plus size here. 

Remember, these run at least a size big and will stretch out, so you want them to fit a little snugly because they will grow.

Finally, the dark wash bootcut jeans featured in yesterday’s Banana Republic Factory round-up are below. 

These are $54 in regular and petite and wear like a trouser jean. 

Keep in mind, the shorter you are the smaller you want the flare of the jean to be. Exaggerated flares will overwhelm you.

How to Wear Bootcut Jeans

If you’re new to our site, it’s important to know that we reuse previously featured items and best sellers in our outfit inspiration content throughout the season so you can get the most out of your purchases.

To Work

Let’s start by pairing the bootcut jeans with a traditional separate blazer.

Our featured blazer above is a popular option from Amazon’s the Drop.

I’ve featured this before and own it in pink and black.

It runs true to size and is available XXS – 5X in ten colors.

Underneath, I’m going a bit extra with this J.Crew ruffle trim top.

But you can wear a classic collar shirt or a simple black long-sleeve tee.

For shoes, I’m using these block-heel pumps from Linea Paolo. We featured these in our most recent Sunday Sales. They are at Nordstrom for only $50, available in matte or patent black, red, nude, and VERY wearable cognac. 

We will see many pointed-toe pumps with block heels in the spring, so scoop these up on sale.

I love this small top handle bag from Amazon.

The quality is fantastic. I have it in brown and black and always get compliments when I carry it.

Finally, in all of today’s looks I’m using this easy pair of huggie earrings.

You can get two (one gold and one silver) for under $25. I like these because they are barely there, and perfect for everyday use.

With a Short Jacket

Yesterday we featured this “Utility” jacket from Banana Republic Factory and I was so happy to see you loved it as much as I thought you would.

It’s nice to have a few different shapes and silhouettes of jackets as options.

And this ones is fabulous for under $60, in regular and petite in XXS -XXL.

Your choice of grey or tan, I’m using the tan below.

Because I see the jacket being worn as a top, meaning, you’re not taking it off, I’m using a square neck tank from Banana Republic.

If you have the Perfect Tank from Nic + Zoe you can wear that as well.

For boots, I found these Sam Edelman Ulissa Bootie in this gorgeous brown suede on sale for about 40% off.

And for the bag, I shared this small Tory Burch small crossbody in our most recent Sunday Sales for 30% off.

They just added this Sandpaper color, which is a lovely go-with everything neutral.

With a Fitted Top

Finally I wanted to share something for a night out.

So I’m starting with this bodysuit at Madewell.

Repeat after me, not everything is for everyone, and that’s ok!

Personally, bodysuits fit me well and I appreciate the smooth, tucked-in look they provide.

And, you don’t have to snap them.

Instead, just tuck it in the extra fabric. The length keeps it place without having to be uncomfortable.

You can also replace the bodysuit with a fitted long sleeve tee.

For this look, a belt adds a nice finishing touch. This double circle buckle is under $20 and comes in a wide range of sizes.

Another boot option is this pair from Linea Paolo.

You’ll get the look of a flat with bit of height to help with the line of the bootcut.

And finally, this inexpensive woven bag from Amazon is a Reader Favorite , works well with the boots and is perfect for a night out.

How to Wear Bootcut Jeans
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Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

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Rachel

Thursday 2nd of March 2023

I just have to say…. I love how you referenced Delia’s 😂😂

Always enjoy reading your posts!

Holly

Wednesday 8th of February 2023

Megan,

Thank you for all of your wardrobe suggestions. I have learned so much! I’m wondering how you feel about mid- rise vs high rise boot cut jeans? It looks like they are coming back in style and I do see that the mid rise style can sometimes be flattering to shorter or petite women? Thank you ~ Holly

J Hill

Wednesday 8th of February 2023

Megan-Love your daily posts. You’ve helped me revamp my closet and wardrobe! BRF has become a staple. I’d urge you to give Grace and Lace jeans a try. You will not find a more comfortable Jean. And the fit profiles videos are super thorough. They have a real following—good size range, no judgement fitting and lots of styles.

Megan Kristel

Wednesday 8th of February 2023

You are very kind, and thank you for the tip!