Our Ultimate Guide To Baggy Jeans

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If you, too, have recently tried on an old pair of skinny jeans and thought, “have they always been this tight????” this article is for you. Denim styles have been getting progressively looser over the years, and now we’ve arrived at – arguably – one of the most exciting (and scary) new denim trends of 2023: a loose, baggy jean.

In order to get some clarity around the baggy jean trend (and loose denim trends in general), I turned to our behind-the-scenes Philly team for help. The goal? To find the best baggy jeans (hint: Levi’s), create a set of styling tips – or heck, even just really good outfits – that this group of highly opinionated fashion girls from three different generations (Gen Z, Milennial, & Gen X), would all wear.

baggy jeans styling ideas for women over 40
Hiiiiii. We can do this.

Not to be confused with flattering, easy-to-wear wide-leg jeans, baggy jeans are loose through the waist, hips, and legs, and exude a knowing sort of cool. They’re the denim goals boyfriend jeans wish they could be.

If this description of baggy jeans is both confusing and/or terrifying…yes!! We understand each other.

Welcome to the new era of denim.

What Are Baggy Jeans?

While retailers play it pretty fast & loose with denim style names (I swear they just assign words at random – ‘mid-rise baggy wide-leg mom jeans’ for example) I think it’s important to be really clear on our definition of baggy jeans – it makes a difference when shopping & styling.

Baggy jeans are part of a whole family of loose fitting jeans, and can have slightly different shapes (barrel, straight, wide-leg). And while baggy jeans can be considered wide-leg jeans…not all wide-leg jeans are baggy. Confused? Thankfully, we have a handy Venn diagram (because of course we do).

what are baggy jeans

The Best Baggy Jeans

While this is highly subjective, there were three specific pairs of baggy jeans that our whole working group loved. They were:

  • Barrel: Free People Moxie Jeans – these are beloved by not just this group, but the wider TME team, too. Even Laura gave them the nod! A few of us may even own them in multiple colors. [S raises hand] I wear one size down from my regular jean size.
  • Straight: Levi’s Baggy Dad Jeans – For an absolute classic pair of baggy jeans, it’s hard to beat Levi’s (plus sizes available here or here). There’s a ton of cool washes, so be sure to check around – Free People consistently carries this style, as does Shopbop. For a twist, this belted style looks seriously fun.
  • Wide-Legs: Madewell Superwide Jeans – Another team (and reader!!) favorite. More classic wide-leg than the other pairs, this one does manage to still have that effortless cool, baggy jean vibe. Might be a good gateway jean into the world of baggy.

11 Styling Tips For Baggy Jeans (Outfit Ideas Included)

So. After spending countless hours researching baggy jeans, trying them all on, then basically relocating all of our collective wardrobes to the office so we could play dress up and argue as a group (gahhhh)…we’ve managed to come up with a few tips. Eleven, to be exact. And while We Have Lots of Opinions, there were a few outfits that emerged as winners.

If you just want to skip ahead to our 8 favorite outfits, a quick video is here:

Ok!! Let’s get into it.

1. The Most Foolproof Outfit: Tucked-In Tees & Trench Coats

Ok – if you just want to zoom to the punch line, let me get right to the point: this is the best outfit for baggy jeans. Simply tuck a slim-fitting tee into your baggy jeans, and finish with a trench coat. Not only is this silhouette flattering and cool, but trench coats have enough sophistication to elevate the baggy jeans…yet are sporty enough to belong.

how to wear baggy jeans 2023

outfit details

The Trench Coats We Can Personally Recommend

While there are tons of trench coats on the market right now (and yay for that), there are just a handful that this team has worn and loved.

I know you’re wondering about shoes – and we’ll get into that!! But suffice to say that ballet flats + trench coats are a classic pairing, and they work really well here, too. That said, any sort of low-profile sneaker (Sambas, Gazelles, Cariumas, Vejas) also work well with this outfit. Chunky sneakers? Much harder. Yes, this is a total departure from old denim silhouettes – that’s why it’s tricky!

The Best Low Profile Sneakers To Wear With Baggy Jeans


2. The Best Shoes For Baggy Jeans: Ballet Flats

I promised we’d talk more about ballet flats and yes: if you get ONE shoe for baggy jeans this fall, make it a ballet flat. Ballet flats are a sleek counterpoint to the oversized, slouchy jean and just completely elevate the look. If you’ve ever wanted to try out the ‘wrong shoe’ theory, it works perfectly here.

how to wear ballet flats 2023

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What I find so interesting about the ballet flat is how it works with any top – even baggy sweatshirts! And while the color of the ballet flat doesn’t really matter (they were all good), we especially loved metallic ballet flats with baggy jeans. Baggy jeans are typically a lighter wash, so I think the light metallic flat just felt very intentional.

The Best Ballet Flats To Wear With Baggy Jeans

Why not mules? Mules often have the look of a traditional ballet flat – even sleeker, actually, with that pointed toe – but since baggy jeans are often full-length, I didn’t love the inevitable walking-on-the-hem that occurs when wearing an open back shoe. That said, if you can stand the feeling, the look of mules is right on.


3. The Baggy Jeans Outfit That Works With Shoes & Boots You Already Own: Tiny Top (or Bodysuit)

We’re going to get into trickier styling moments, but once again, let’s start simple: tiny tops. Whether it’s a slim, tucked-in tee, a bodysuit, something silky (or cropped), the small-top + loose-bottoms combo is a solid move. One that’s so foolproof it looks good with the widest range of shoes & boots.

the best baggy jeans

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In general, we’ve found shoes or boots with some element of femininity – straps, pointed toes, heels – look the best with baggy jeans. While this is not an exhaustive list, here are the shoes & boots we recommend starting with:

The Best Shoes & Boots To Wear With Baggy Jeans

  • Ballet Flats
  • High Heels (of almost any kind)
  • Low-profile Sneakers
  • Nike Dunks (or Jordans)
  • Birkenstocks
  • Sleek Loafers (not lug sole or chunky)
  • Heeled Boots (pointed toe, stiletto heel – best in lighter colors like tan or even white)
  • Cowboy Boots
  • Platform UGGs

Tiny Tops To Wear With Relaxed, Loose Denim


4. Go Sporty: Cropped Jackets & Baseball Hats

Because baggy jeans are inherently casual, they pair easily with sportswear. But to keep the outfit looking intentional (rather than sloppy), short, sporty jackets are the way to go: windbreakers, bombers, even short puffer coats are perfect. Bonus points for a baseball hat.

baggy jeans outfit idea

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The key here is to show off your waist. So those old, “short-ish” jackets (that hit at mid-hip) are not really what we’re looking for. You want something that hits closer to your waist (or cinches in at the waist), especially if you plan to zip it up.

The Best Sporty Jacket Types For Relaxed Denim

Again, this is not an exhaustive list, but here are three sporty jacket types that seem to work especially well with baggy jeans:

  • Short Windbreakers (With a Drawstring Waist) – My favorite windbreaker (pictured above in green) is from Halfdays. It’s roomy enough to fit over sweaters, but cinches nicely in at the waist, and is available in plus sizes, too. Free People’s Way Home Packable Jacket also works (and comes in a zillion colors) and SPANX’s Organza Windbreaker is really chic (plus sizes also available).
  • Bomber Jackets – Whether you go with a shorter, cropped bomber jacket (we love Athleta’s) or an oversized bomber (Topshop makes the best one – available in corduroy, faux leather or cotton), oddly enough, both styles look great with baggy jeans & baseball hats.
  • Cozy Fleece Jackets – Again, the key here is to find a shorter version that hits at the waist, or at least cinches in at the waist. Vuori’s super snuggly one works (I have it in ivory, but they just released new colors), or this Adidas cord + fleece jacket would be epic with baggy jeans.
  • Oversized Vests – While these do not fit in the category of ‘short jacket’ they are sporty. And I’d be remiss if I didn’t mention how much we loved Free People’s In A Bubble Puffer vest with baggy jeans.

Baseball Hats We Love


5. How To Wear Baggy Jeans With Sweatshirts (Or Slouchy Sweaters)

And now we’re getting into trickier territory! We’ve found that, in general, if you want to wear comfy ol’ tops with comfy ol’ baggy jeans (and yes, yes we do) then you’ve got to either show off your waist somehow (full tuck, half tuck, cropped top, maybe add a belt?) or just lean into the baggy-on-baggy look…but offset with sleek footwear.

outfit details

In general, if going for a baggy-on-baggy look, it helps if the rest of your look is on point. As we mentioned, ballet flats are our top choice, but other shoes can work – just be sure to carry a cute bag and mayyyyybe do your hair/makeup that day. I know that makes a huge difference when I’m trying out these trickier looks.

Low profile sneakers? We’ve also found that low profile sneakers (Sambas, Gazelles, Vejas) vibe like ballet flats, which is why they work so nicely here, too.

Now let’s talk about chunky sneakers: I know we still have them in our closets, right? Chunky sneakers can totally work with baggy jeans, but because they break up leg line, they tend to work best when the outfit has a clearly defined waist. A boxy, cropped top is our top choice, but any sort of tiny top that shows off a waist would work with chunky sneakers.

Comfy Tops To Wear With Loose Jeans


6.  The Most Foolproof Top For Baggy Jeans: The Capelet

If you are tempted (but slightly frightened) by the baggy-on-baggy look, we have a shortcut: Frank & Eileens genius capelet. It’s not too long, nor too short, and looked good with literally every. single. shoe.(or boot) we tried. It’s baggy jeans’ BFF.

baggy jeans easy outfit ideas

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This capelet is hard to find a dupe for – the genius lies partly in the fabric (which is decidedly lux for a “sweatshirt”), and partly in the cut. But we did manage to find a few capelets that might be worth trying.

Our Favorite Capelets/Ponchos


7. How To Wear Baggy Jeans With Long Tops

Once we venture into the realm of a truly long top – not just baggy, mind you, but menswear shirting or maybe even tunic-style tops – baggy jeans need sleek footwear. For most of us, that means heels. A sleek stiletto, or a pointed toe really help to define a leggier line. And these feminine shoes look especially amazing when paired with menswear-inspired shirts.

How to style an oversized button-up

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A note for the tall: You probably don’t need heels. But the sleek line, even in flats, will help keep the look intentional, not sloppy.

A note for the short: if the shirt is overwhelming, try cuffing the sleeves. It makes a huge difference.

Our Favorite Oversized Button-Ups


8. How To Style Baggy Jeans With UGGs

If this seems like an oddly specific shoutout…it is. But what good is a baggy jean styling article if you can’t actually wear these very comfortable jeans with very comfortable boots? The key to wearing UGGs with baggy jeans is, once again: show off that waist.

UGG outfit ideas with long, loose jeans

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If you happen to be in the market for new UGGs, we all LOVED how the newer, platform UGGs looked with baggy jeans. There’s something about that smooth sole that elevates the look (both literally and figuratively – ha!).

Our Favorite UGGs


9. How To Style Baggy Jeans With Western Boots

(aka: Balancing The Yeehaw)

As a boot shape, cowboy boots are a no-brainer with baggy jeans. They fit easily under the hem of the jean, most have some sort of walkable heel, and the pointy toe is sleek – exactly the kind of boot that elevates the baggy jean outfit! The trick, though, is to balance out the, uh, ‘yeehaw‘ factor of the cowboy boot. Our favorite way to do that? By adding in preppy elements: nautical stripes or chunky, cozy knits.

how to wear cowboy boots with baggy jeans.

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Don’t be afraid to play around with cuffing your baggy jeans. In general, if the boot is flat and the top is short…a cuff works.

Western (Cowboy?) Boots We Recommend


10. The Best Boot For Baggy Jeans: Light, Sleek Boots

As we get used to a new denim silhouette, I do think our eyes need a period of adjustment. And the easiest way to ease that transition is to think monochrome. Since baggy jeans are, by definition, a bit broken-in, we’ve found that a lighter shoe (tan, taupe, light gray, ivory, blush, even white) worked fairly flawlessly with baggy jeans.

The best ankle boots for baggy jeans are tan, taupe or white.

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Darker boots (black, oxblood) provided so much contrast in both color and vibe that it often felt jarring. I’ve always been a huge fan of tan ankle boots (I find them more useful than black), but if you have an old pair of white ankle boots still sitting in your closet, baggy jeans are a perfect way to make them feel fresh.

Shop Our Most-Worn Tan Booties


11. How To Wear Black Boots With Baggy Jeans

That said…I know most of us already have black boots in our closets – can we really not wear them with baggy jeans? And the answer, of course, is: it depends. After hours of try ons, we all found ourselves struggling with the chunky, lug-sole boot shape: Doc Martens, lug-sole chelsea boots, even chunky loafers were tricky.

Why chunky, lug sole black boots are hard to style with baggy jeans.

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In general, if you want to wear black boots with baggy jeans, you’ve either got to balance the outfit by adding in some black (and/or heavier texture) up top…or you’ve got to pick a black boot that’s sleek, not chunky. Black sneakers with a contrasting sole (white, or gum sole) also helps to keep the black shoe from being too overwhelming.

Shop Black Boots To Wear With Relaxed, Loose Jeans


And thank you for coming to our Ted Talk. 😉

xo,

S

Oh hey pinners…