The 6 Best Madewell Jeans (and how to style them)

Over the years, I’ve tried jeans from about 30 different brands. (I once tried 15 brands just to find the perfect pair of white skinny jeans.) And while I don’t think I’ll ever be totally done shopping for jeans, I have landed on a few brands that I LOVE and order from year after year.

One of my go-to brands for jeans is Madewell. They have a cult following for good reason. They carry so many styles, every size under the rainbow (they’re extremely size-inclusive and have tons of great curvy jeans), multiple rises for each pair, petite and tall lengths, and tons of washes. If you can drop by in person at one of their stores, be sure to visit the Madewell Denim Bar, which has an extensive selection to try on.

With so many options, however, it can be challenging to figure out which ones are best, especially if you shop online. So, in today’s post, I’m sharing a roundup of the best Madewell jeans and my thoughts about them. Hopefully, this helps you narrow down your favorites or find a new pair to love!

Madewell Jeans Size Guide

First, let’s go through some sizing information so that you know exactly what size get when you place your order. Madewell is extremely size inclusive with options ranging from size 23 to 33, 14W to 28W, and three inseams: Petite, Plus, Standard, and Tall.

Do Madewell Jeans Run True-To-Size?

In my experience, Madewell jeans fit exactly as described on the website. Some of the styles are designed to sit low on your hips with a relaxed, baggy feel, and when that’s the case, Madewell notes it and suggests sizing down for a closer fit. They also include fit notes if they receive feedback that the jeans run small or large based on reviews.

Madewell has an entire page on its site dedicated to a “denim fit guide,” where you can read about the fabric and materials of each pair of jeans. It walks through the different stretch options and the difference between the regular and curvy fit and teaches you exactly how to measure yourself for your jeans. It goes above and beyond to make sure you feel confident with your sizing choice.

If you want someone to walk you through the sizing options, check out Madewell’s virtual styling option.

Madewell Virtual Stylists

This is one of the coolest things I’ve ever seen from a brand. Madewell offers the option to book a video call with one of their stylists to talk through all things sizing. The appointment is complimentary and you actually earn 250 points (which translates to $10) for each appointment that you attend. How cool is that?? Read more about this styling option here.

The 6 Best Madewell Jeans

1. The Perfect Vintage Jean

The Perfect Vintage Jean from Madewell is what I call my OG pair of Madewell jeans, even though I had a few pairs before these. They were my gateway into non-skinny jeans and the first pair of straight-leg/mom jeans that looked good on my petite frames (I’m 5″1 and was hesitant to try them).

This pair is a great option for women looking for a style other than skinny jeans. Think of them like an “intro pair.” They’re snug and flattering on the bum and through the hips and thighs, but they get looser at the bottom, giving them a more relaxed feel. They’re cropped slightly above the ankle (key for cropped pants) and high-waisted. Win-win-win!

I’m petite (5’1″), so I ordered the petite length (they have petite, regular, tall, and plus-sized options) in a size 26. I wish I had sized down in these, since they stretched out over time. This pair has a slight stretch to them, which makes them very comfortable for all-day wear, but they don’t hold their structure as well as a pair of jeans that are 100% denim. I recommend washing and drying this pair often to shrink them back after each wear. It’s a matter of preference, but I like to have a few pairs of jeans with stretch and a few without. Since I wear them practically non-stop year-round, I like options.

The Perfect Vintage Jeans are available directly from Madewell and are currently on sale!

The photos below are from a few years ago, and the wash of the Perfect Vintage Jeans I’m wearing below is no longer made. The pair linked above (the berdelle wash) has the most similar coloring.

I style them with sneakers, sandals, and heels.

2. Kick Out Crop Jeans

These used to be called the Cali Demi-Boot jeans, but what does that even mean? I’m thankful they’ve changed the name to something that makes more sense: Kick Out Crop. These are cropped jeans with a tiny flare at the ends. They’re flattering with all sorts of shoes because they show your ankle a bit, and the wider bottom balances slightly chunkier shoes, like sneakers.

Madewell makes many variations of this style, and I own the Pure White wash in the Kick Out Crop. I wore them throughout the spring and summer and can’t say enough great things about them. In the photos below, I am wearing a size 25 Petite, and they are a perfect fit.

This cut is a little trendier right now, for good reason! Skinny jeans are classic, but this new cropped style is flattering, especially for someone petite. The Pure White wash (which is what I have) is the perfect shade of white: not too tight, not too loose, not too thin, and also not see-through. If you are petite (5’4″ and below), I suggest the petite inseam. I like my cropped straight-leg jeans to hit above my ankle.

3. The Darted Barrel-Leg Jean

New this year to Madewell’s denim selection is the Darted Barrel-Leg Jean. Barrel-style jeans are a big trend this fall – they give the illusion of bowed legs and have a relaxed, casual fit. While I was unsure about the barrel-leg trend on my petite frame, I ordered these jeans as soon as my size became available. I particularly love that the barrel fit is much more subdued than some other options at different retailers this fall. The leg isn’t super wide, but it does have the arched look that I was going for. Since these come in a petite fit, I knew they’d be my most flattering barrel jeans option. Photos to come, as soon as these arrive!

4. Stovepipe Jeans

If you’re looking for a not-skinny-but-not-straight pair of jeans, the Stovepipe jeans from Madewell are a great option. They have a fitted leg and bum, but the ankle is slightly looser, which gives them a polished, tailored look. I don’t own this style yet. However, I want to snag a pair to style with loafers and flats since the Kick Flare can feel a little too playful at times. The Stovepipe jeans look great with flats.

There are a ton of different fits of the Stovepipe style. However, I love the basic Stovepipe Jean black rinse.

5. The ’90s Straight Jean

Next on my wishlist is the Madewell The ’90s Straight Jean. I have a pair of ’90s Straight Jeans from Abercrombie that I absolutely love. See photos in this Abercrombie Jeans Review I shared. So, I want to see how these compare. When I first tried this style from Abercrombie, I wasn’t sure how to style the full-length jeans with such a relaxed feel, but now I love them!

You wear the exact same shoes you normally would. Then, you just have to get over the mental hump of them looking a little different than you’re used to. They are a fun trend that’s coming back, and I’m here for it. Madewell’s ’90s Straight Jean comes in a ton of washes and fits. However, the pair I’m eyeing is the cream colored Vintage Canvas. I love white jeans in the spring and summer, but my Pure White washes feel a little bright for the winter. This cream-colored pair is the ideal winter white!

6. The Perfect Vintage Wide-Leg Jean

I can’t wait to get a pair of wide-leg trouser style jeans! The Perfect Vintage Wide-Leg Jean is my favorite Madewell version, especially the Lavaca Wash with the patch front pockets.

This style is not cropped, which means you’ll want to pair them with shoes that allow the hem to “kiss” the floor. I typically wear heels when I style wide-leg full-length jeans, but every once in a while, I’ll wear sneakers or flats. The key is to hem the jeans to just barely touch the floor in the shoes you’ll wear most often. Read more about how to style wide-leg jeans in this blog post.

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