Welcome! I’m Meg — founder of Jean Genie Vintage, your curated online vintage denim destination — built on over a decade of sourcing, studying, and wearing vintage Levi’s, with clear-eyed reputable advice on fit, quality, and value.
There’s a real difference between wearing your actual boyfriend’s jeans and finding a pair that gives you that same easy, borrowed comfy-cool factor — yet tailored to your own proportions. One is a hand-me-down. The other is intentional — and is more flattering to your body type!
We’ll never forget pulling on those infamous Current/Elliott Boyfriend Jeans back in 2008 — how different they felt from anything we were used to — and yet instantly, undeniably cool.
That “perfect” boyfriend fit — the one that feels effortless, slouchy, and still intentional — is still going strong, showing up everywhere from moms on the go to the fashion “it girls” on the street. Getting this look isn’t about sizing up blindly. It’s about controlling where the denim sits, how it breaks, and what it refuses to do.
I cannot tell you how many times I’ve been sent the post with these photos of Morgan Stewart, in her perfectly slouchy sexy 501s — asking how do I get this look. So I’ll say a few things and then move along.
We/I do not have the same body that Morgan has. Read: no two people have the same body type. And for that reason alone, there is no way I can honestly answer that. What works for her, will not work the same for most.
We do not know if she has altered these in any way.
She did not source these from me.
They are superb.
Morgan — Can you hear me calling… out your name…? (In my best Christine McVie voice) When you are in need of a new denim dealer, my DMs are open. xo
Where to Start: Know Your Measurements
Before you even think about tags or sizes, you need to know your flat lay fitted measurements —the measurements of your best-fitting 100% cotton jeans laid flat. These measurements should live in your phone’s notes.
This is your baseline.
Everything else is just deviation.
The Art of the Slight Slouch
If you want that “I just threw these on” ease — but still want your body to exist inside the silhouette — you’re not going oversized. You’re going slightly adjacent. Which is still cool. And still uber comfy.
Add about ½–¾ inch to your flat lay waist (that’s 1–1.5” total around).
So if your fitted waist is 15”, you’re looking for something around 15.75”.
So really spell it out, you will be going from what I call (in my shop), an actual 30 (15” flay waist) to a 31 (15.75” waist — I round down).
What happens here is subtle but important:
The waistband loosens just enough.
You can hike them up, belt them, cinch them.
You get that soft paper-bag effect without losing your shape.
This is the gateway fit. Controlled nonchalance.
The Real Boyfriend Fit: The Commitment
Now… if you actually want the full look — the one that reads borrowed, broken-in, and a little bit defiant — you have to go a little further.
Add about 1.5 inches to your flat lay waist (3” total around).
A 14” becomes 15.5”–15.75”.
Spelled out: you size up from an actual 28 (in my shop) to an actual 31.
This is where things shift:
The waistband drops to rest comfortably on your hip bones.
The rise relaxes — and yes hangs a bit low. Crotch drops. Embrace it.
The back panel stops “hugging” and starts hanging.
And no — your bum will not be the main character anymore.
That’s not a flaw. That’s the point.
In fact, when the jeans are big enough to sit fully on your hips, something counterintuitive happens: your bum fills the upper back panel, and the pockets fall slightly lower, creating that off-duty, undone line that makes the whole thing work.
Go too small, and you’re stuck in between — neither fitted nor fully slouchy.
Just a bit confused.
The Style (and year) Can Matters More Than You Think
Not all vintage Levi’s behave the same — and this is where most people need a little help.
Hi! I’m Meg. I’m here to help!
STRAIGHT BODY TYPE:
If this is you and you want that perfect slouch, start with a Levi’s 505. They’re naturally straighter through the hip and thigh, which means that even when you size up 3” full inches (1.5” added to your flat lay waist) they hang without giving you too much of that saggy bum effect.
If you’re set on Levi’s 501, aim for pairs from the ’80s through about 1994-ish. Those years were cut slimmer through the hips/bum than their mid-to-late ’90s counterparts, making them far more flattering when worn oversized.
Later cuts tend to add bulk where you don’t want it (if you’re a slim build) — especially if you’re chasing that easy, draped boyfriend line.
A year or so ago, I did an instagram story showing the above pair of my go to boyfriend 501s — full 360 — and spoke to it. It’s helpful (I think). Watch it HERE.
CURVY OR HOURGLASS BODY TYPE:
If this is you, you’re going to be better off sticking with that 501 button fly. And your best bet will be sizing up in 501s from the years: 1995 to 2001. They cut them a bit more relaxed in the thighs/hips/bum during those years — as opposed to 80s to 1994.
I have never been, nor will I ever, referred to as “curvy”, or “hourglass”. Nor petite (I’m 5’10”). So I am bringing in one of my besties who is both.
Let me introduce you to my dear friend, Kathryn, founder of Haus of Phoenix and Inky Phoenix Press. She is the opposite of my body type, and yet we wear the “same size” in many things — though how clothing hangs or hugs her differs from me. She is also a verified card carrier of the JGV (Jean Genie Vintage) Club — rocking all styles, not just 501s.
For reference: Kathryn is 5’2”. She is a typical US Size 4, or Small. Her Fitted 501 is about a 14.25/14.5”.
Above: 1998 USA Levi’s 501 (all the same pair)
Flat lay waist: 15.5” (actual 30) — sized up 1” from her fitted flat waist measurement
Above: Late 1980s USA Levi’s 517 (both same pair)
Flat lay waist: 16.25” (actual 32) — sized up 2” in the waist, because hips run more narrow in a 517 — and resulted in the hip measurement being only 1.5” bigger (3” total)
Great example of how are curvier bodies have to almost go solely off the hip measurements when it comes to vintage Levi’s styles: 517 and 505 and 646.
Side note for the hourglass folks: This can work with older years or with 505s too, but you’ll need to make sure that your hip measurement increases at least 1.5” (3” total) from your fitted hip measurement. Similar to the 517 example above.
A Quick Reality Check on “Vintage”
**Because I love to really imprint this into your brains.**
In this article, I am only speaking to true USA Made Vintage Levi’s here.
Because it matters. At least to me — and it should to you too, if you are paying “vintage Levi’s prices”.
You can learn more about how to tell the difference between “used” and “vintage” Leiv’s HERE.
You’re probably thinking — if you know me by now — here she goes, climbing right back onto her soapbox. And honestly, I will — until more people get it.
History fact: Levi’s stopped making jeans in the USA in 2002.
I personally don’t sell anything other than USA-made, true vintage denim — which technically means over 20 years old, but using that 2002 cutoff, everything in my shop is at least 24 years old.
The difference isn’t just sentimental — it’s structural. It’s in the unmatched integrity of the fabric, the superior precision of the seams, the consistency in cut, the natural evolution of the fades, and the quiet way the denim withstands time.
You will feel it immediately. Trust me.
The Hard Truth About the Baggy Bum
Let’s be clear: If you don’t (or won’t) subscribe to a slouchy fit or the uber-relaxed silhouette isn’t for you — that is A-OK!
Boyfriend jeans don’t sculpt. They relax. They shift attention away from form — towards attitude and unexpected proportion.
Trying to force them into being flattering in the traditional sense is how people miss the point entirely.
But, if it’s not your thing. It’s not your thing. Congrats on staying true to your own personal style.
Styling: All In or All Contrast
Once the fit is right, styling becomes the easy part.
You have two honest options:
Go all in!
Oversized on top, oversized on bottom. Volume on volume. It reads intentional, directional, a little irreverent. It silently screams cool with an attitude. With so much mystery to the eye of the beholder.
In this case, you can really pair with any shoe — whether it’s something feminine, a flip flop, boot or sneaker. And accessories? You do you.Create tension.
A fitted, feminine, and/or cropped top paired with that slouchy denim? It’s a yes for me. Something that reminds the eye there’s a body under all that denim below.
A feminine shoe bookends the cool contrast. A ballet flat. A sexy heel. Strappy sandal. Perfection.
I’ll take a moment for a shameless pat on my back. Jenna Fucking Lyons wore a pair of vintage 501s — that I sourced for her — to the Victoria’s Secret Show in 2024.
Her ask: “I want them really oversized.”
Say less.
And well — I mean. No notes.
But a Final Note
The perfect boyfriend fit isn’t about looking smaller, tighter, or more “flattering.”
It’s about understanding space — and what happens when you let go of the idea that denim has to perform for your body. And you stop dressing for the male gaze.
Fuck — yes. How refreshing!
Sometimes the best thing a pair of jeans can do is back off a little.
And let you take up the room.
Forever in blue jeans.
XO, Meg
LOOSE THREADS: You might as well pull..
Want to learn about basically the opposite of this article? And how to get that FITTED Levi’s bum? I got you covered in my article: Hips Don’t Lie.
Some of my favorite shirts to wear with baggy “boyfriend” jeans can be found HERE.
If you have something you’d like me to write about — please feel free to leave me a comment. I love hearing from you. I’m new to this whole Substack thing — but I think I’m going to like it here.
I made your Substack. I HAVE ARRIVED. 😎
This is priceless info. Thank you for this.