Baggy Jeans Are The Next Big Denim Trend: Do We Care?

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We’ve been cropping our jeans for so long, you guys….SO LONG. I am, after years of mom jeans and cropped skinnies, a fearless, scissor-wielding maniac, and there’s no hem I can’t shorten in seconds. (Hello, ankles!! Welcome to the world!)

But fashion is a fickle friend, so after years and years (and years) of cropping my denim, I’m feeling alllll the feels over this baggy jeans trend.

And frankly, after spending the past year in almost nothing but sweatpants…a pair of oversized, slouchy denim feels like the best kind of bridge back to The Land of Real Clothes.

Baggy Jeans > Skinny Jeans might become my 2021 motto.

Are Baggy Jeans Different From Straight Leg Jeans?

Baggy jeans are loose through the hips and legs, with a very straight leg line — these are not flare jeans. Flares are typically tight to the knee, then swoop down over the shoe, covering it completely. While some baggy jeans may be wide enough to cover the shoes…I much prefer the pairs that are a little more reigned in. Think loose, boyfriend jeans with a full-length, straight leg that is ever-so-slightly too long. The kind that bunches a bit at the top of your shoe.

The vibe is decidedly ’90s.

If skinny jeans are out, baggy jeans are decidedly IN! Relaxed, straight leg & loose-fitting, hello '90s vibe. Like sweatpants, but denim — yes! Here's how to style 'em.

sweater | jeans | sneakers | similar bag | mask

Since trends rarely return in their original, unaltered form, the baggy jeans of today have a much higher rise than the ’90s version. And I think that’s what makes this trend surprisingly wearable. High-rise jeans lengthen your leg line, and — if you show off the waist by tucking or keeping your top a bit cropped — will create some shape (or at least the illusion of height).

If skinny jeans are out, baggy jeans are decidedly IN! Relaxed, straight leg & loose-fitting, hello '90s vibe. Like sweatpants, but denim — yes! Here's how to style 'em.

sweater | jeans | heels | straw bag | mask

Of course, if you’re tall, the trick is going to be finding jeans long enough. But don’t worry…this trend is just gaining steam, so expect to see more iterations of baggy jeans hitting stores.


What Shoes To Wear With Baggy Jeans?

Whenever I’m trying out a new denim trend, it’s almost always the shoes that trip me up. I’m such a creature of comfort, and am not willing to wear uncomfortable shoes (like…ever). So if a new trend can work with my existing go-to shoes…I’m much more likely to embrace the trend.

While I’m planning to do more “research” (ha!) into the topic of baggy jeans & shoes…I have found two shoe types that pair especially well. They’re practically foolproof.

Styling Baggy Jeans With White Leather Sneakers

If skinny jeans are out, baggy jeans are decidedly IN! Relaxed, straight leg & loose-fitting, hello '90s vibe. Like sweatpants, but denim — yes! Here's how to style 'em.

sweater | jeans | sneakers | similar bag | mask

The fact that these baggy jeans work with adidas Superstars made this a much easier trend to lean into. It’s been chilly as of late, so I’m wearing my baggy jeans & sneaks combo with a sweater, but this pairing works just as well with a tucked-in tee or strappy little tank top (like I wore on IG, here). I’m excited to play around more with this combo.

If skinny jeans are out, baggy jeans are decidedly IN! Relaxed, straight leg & loose-fitting, hello '90s vibe. Like sweatpants, but denim — yes! Here's how to style 'em.

sweater | jeans | sneakers | similar bag | mask

Fit notes
The baggy jeans I’m wearing are my longtime favorites: Levi’s 501s. Instead of picking up my usual cropped pair (me in my cropped Levi’s 501s), I went with the 501 Original Fit due to its longer inseam length. My exact pair can be found at Nordstrom, with a 30″ inseam. However, if you go to Levis.com, you can find my exact pair in both 30″ or 32″ inseams. I much prefer my 501s a bit loose, so I’ve sized up one full size from my typical denim size. (I’m wearing a 27 if anyone cares.)

This cropped cashmere sweater has become my wardrobe hero as of late, and if you are a longtime reader, I’m sure you are sick of it by now. I’m wearing a size small, and it’s now sold out at Saks (but on sale at Shopbop).

I have fancier sneakers, but the ones I go back to over and over and over again are my adidas Superstars. I really need to write an ode to them. There’s not a single trip I’ve gone on (in the last 2-3 years) where I haven’t packed these sneaks. I happen to be wearing a limited edition (cause why not?), but the classic adidas Superstars work just as well.

Lastly, if you haven’t yet gotten addicted to Clare V bags…maybe just move on. Nobody needs these. That said…I don’t quite know why I never seem to tire of these bags…but I’ll pick these over Chanel/YSL/whatever it bag any day. (I *did* write an ode to Clare V’s Pot de Miel bag, as an example.)


Styling Baggy Jeans With Heels

If skinny jeans are out, baggy jeans are decidedly IN! Relaxed, straight leg & loose-fitting, hello '90s vibe. Like sweatpants, but denim — yes! Here's how to style 'em.

sweater | jeans | heels | straw bag | mask

Heels, of course, always look good with denim. But I wanted to see if baggy jeans would work with fancy, dramatic heels and they DO.

That said, I probably wouldn’t wear this exact outfit again: there’s a bit too much going on. The bagginess of the jeans themselves is almost like an accessory, so in this case, I wish I was carrying a sleeker bag. OR I wish I was wearing minimalist nude sandals; that would work, too.

If skinny jeans are out, baggy jeans are decidedly IN! Relaxed, straight leg & loose-fitting, hello '90s vibe. Like sweatpants, but denim — yes! Here's how to style 'em.

sweater | jeans | heels | straw bag | mask

Truth be told I’m wildly obsessed with this straw stunner and my excitement may have blinded me a little bit. Rest assured I have big plans for this bag (just maybe not with this particular jeans + heels combo).

If skinny jeans are out, baggy jeans are decidedly IN! Relaxed, straight leg & loose-fitting, hello '90s vibe. Like sweatpants, but denim — yes! Here's how to style 'em.

sweater | jeans** | heels | straw bag** | mask

Fit Notes: I’ve already talked ad nauseam about my jeans & sweater above…but can we discuss this gorgeous straw bag from AAKS?? It has an inner liner to keep your valuables in place and pom-poms. AAKS is a Black-owned business, and each bag is handcrafted in Ghana. I couldn’t be more thrilled that Nordstrom is now carrying a bunch of AAKS bags. Check ’em out.

Lastly, I’m always happy to wear these (admittedly) slightly over-the-top Loeffler Randall heels. These statement heels are surprisingly walkable, too, thanks to the sturdy heel and ankle-strap.


Where To Buy The Best Baggy Jeans (By Height)

If skinny jeans are out, baggy jeans are decidedly IN! Relaxed, straight leg & loose-fitting, hello '90s vibe. Like sweatpants, but denim — yes! Here's how to style 'em.

I’m kiiind of a die-hard Levi’s girl: their washes set the standard for that perfectly-faded-blue, and their commitment to sustainability is impressive. That said, I scoured the internets for a few additional options (and was able to find other sustainable pairs, too). And since a key part of this look is finding full-length jeans, I’ve broken my favorites out by inseam length.

For funsies, let’s start with the skeptics first.


The Best Baggy Jeans For Tall Women (Inseam 33″ – 36″)

OK, you long-legged gazelles…here ya go.


The Best Baggy Jeans With A 32″ Inseam

I’ve found that many brands don’t keep a consistent inseam length as the sizes change (even within the same style), so there’s a bit of a fudge factor here. That said, these are the jeans that retailers claimed were consistently longer than 30″.


The Best Baggy Jeans For Petites (Inseam 30″ & Under)

At 5 feet, 3-ish inches tall…this category is where I typically land, especially if I want to wear these jeans with sneakers. As I mentioned above, my beloved Levi’s come in at 30″…but only if you get the original fit, not the cropped fit. Most straight-leg jeans these days seem to fall between 28″ – 30″ so there’s a ton of choice in this category.

What say you, readers? Are you tempted by this baggy jeans trend? (And if you’ve found a perfect pair…SPILL.)

xo,

S

26 COMMENTS

  1. Any thoughts on how these 501s would fit a more pear-shaped gal? I love the look on you. Reminds me of my 90s Levi’s for sure. Worry they might not look as “baggy” on my pear bod.

    • Our next team try-on is a pair of Levi 501s (which reminds me…I think I’m the last one needing to add my pic to the article, oops). Anyway, you’ll be able to see how different body types look in the 501s. I know Scotti considers herself pear-shaped, and I think she loves them. I really would try sizing up – maybe even 2 sizes?? It took me a while to figure out sizing, but once I did, I LOVED them.

  2. So curious about the baggy jean. I have a pair of dad jeans that might work – if it’d stop snowing in Colorado, I’d like to try them with a strappy, flat sandal. I’m focusing on only warm weather looks right now to preserve my sanity.

    • I get this. Let me know how it goes. The Dad jeans I have (including my usual 501s) weren’t *quite* long enough to really get this look down. But other than leg length, I think the styles are identical.

  3. I’m not sure I can embrace the full on baggy jeans with an inseam that goes all the way down to the sneakers. However, if you roll them a bit for me they would crossover from ‘dad’ jeans (as in they look exactly like what my dad wears) to a cuter boyfriend jean. I love the way a baggy boyfriend jean rolled up at the ankles looks with a simple black v-neck t-shirt. =)

  4. Wow, I hate them! But I am historically several years behind the curve on denim trends (just phasing out my last pair of skinnies) so I’ll probably have 4 pairs of them in about 3 years.

    • HAHAHAHAHAHAHA – I totallllly get this. I’ve completely stopped saying ‘NEVER’ on this blog because, over the last 13 years, I’ve been bitten by exactly 100% of my “never” declarations. SIGH.

  5. So my cousin recently gifted me a pair of Levi’s 501 straight leg jeans that didn’t fit her (they DO run small!). They’re thicker and actually weigh more than my usual denim. I believe they have either no stretch or very little, and you can feel the difference. I can’t decide if I like the heavier feel yet. My pair hits at the ankle and they’re pretty fitted, but I can imagine a looser, longer (baggier) pair would be more comfortable.

  6. I recently bought the Pistola Cassie jeans and I love them but also feel like I’m trying to look like I did in high school so may be having a fashion midlife crisis (I’m 41 so baggy vintage 501s from the flea market were my high school staple)? They’re a 31″ inseam and just a touch too long on me (I’m 5’4″) but I’m having fun playing around with styling them. I’m not thrilled, though, about the return of long jeans and pairing them with shoes. I remember needing to have jeans for sneakers/flats and jeans for heels and I’ve so enjoyed the cropped jean trend for simplifying life in that regard!

  7. Yes! I am so so happy for full-length jeans. I have had it with the crops. Part of that is living in New England and being sick of cold, and part is being 5’10” and needing a longer inseam to even have a good crop. And baggy, I love you. I never loved skinny jeans. I was born for this moment, or maybe I really just never left the 90s.

  8. I bought that exact pair a few weeks ago and love them, but I bought my true size—which felt too tight initially but stretched to fit with a day or two of wear. I love them—but in my normal size they are fitted/snug in the butt and waist—which I really like with the looser leg.

  9. Ack! Though I was committed to these throughout college and beyond in the 90s, I don’t think they’re especially flattering, and probably less so now that I’m no longer inhabiting a 20-something body.

    Designer jeans taught me a lot about the magic of pocket placement, and feel like Levi’s misses the mark with the wide low pockets.

    I want early aughts flares to return!

  10. I’m with you. I look at these pics and I think “really?”. It’s kind of how I feel when I look at these super high waisted pants that make asses look flat as pancakes…really? I clearly have NO idea what looks good anymore and will be wearing my skinny jeans forever. Are skinny jeans the new “mom jeans”😂. At least my butt looks round and my man digs them.

  11. I don’t know if I can get on board with this, but props for posting a pair with the giant inseam I’d need to pull this off! Now I have to actually consider it, haha.

  12. I am looking forward to the TME team try on. I so want to love these jeans and yet, I cannot imagine how to wear them and not look sloppy- especially at work. And I hear you on the shoe pairings. I could use a whole tutorial on what shoes to go with which jeans.

  13. Skinny jeans was the greatest fashion development for the past two decades. I see what’s happening here. Baggy jeans is trying to ease itself into the fashion industry through the back door. Sneaky sneaky. Well it’s not going to work.

  14. So, my exact pair of 501s in the 32” length came yesterday. One size up from my usual. Two sizes up was not available in the 32” length, so I couldn’t try that. I am almost 5’ 7” and these give me just a bit of puddling at the ankle. Not quite as much as Shana in her photos. As what I call an athletic pear shape, they also are not quite as baggy on me through the hips, booty and upper thighs. I think two sizes up would require me to have the waist taken in, though, as I don’t carry a lot of weight in my middle. I actually think I could wear them long or cuffed. Love the wash, and they will break in wonderfully. I am struggling a bit with what tops look good with this looser bottom and high waist. Many of the tops in my closet were a bit too long. On the fence about keeping. Would love to see what else you pair with these.

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