Fall Denim Made Easy: My Favorite Fits of the Season
SWEATER(XXL) | JEANS (16/18) | SIMILAR JEANS(USE CARALYN15) | FLATS | SIMILAR FLATS
LET’s TALK ABOUT
STYLING FALL JEANS
When it comes to fall fashion, nothing beats a great pair of jeans. They’re classic, they’re versatile, and they evolve with the season—think richer washes, updated silhouettes, and endless outfit combos.
Lately, I’ve been gravitating toward styles that feel equal parts pulled-together and comfortable, from effortless kick flares to tried-and-true staples that work for everything on my calendar. Whether I’m dressing them up with heels and a blazer or keeping it casual with sneakers and a knit, these are the jeans I’ve actually been reaching for on repeat.
PS: Not sure what shoes to wear with your denim?
I’ve got you covered in this guide with everything from sneakers and flats to boots and heels.
JEANS (1X) | SHOP THE LOOK
JEANS (18) | SHOP THE LOOK
JEANS (16) | SHOP THE LOOK
JEANS (18) (PLUS SIZE JEANS) | SHOP THE LOOK
fall denim 2025
My Favorite Styles LATELY
Cropped kick-out jeans (like these — use CARALYN15 on your first order or with a new email address) are such a great way to ease into the wide-leg world without going full drama. They’re super flattering on a range of shapes and pair well with flats, sneakers, or a little boot. I’ve been calling these my “out to dinner” jeans because they feel polished but still so comfortable.
A great black pair of jeans like these is truly a closet MVP. I cannot stand when black denim fades after a couple of washes, but this pair holds up so well. The color stays rich, the fit stays flattering, and they go with literally everything. Sleek, timeless, and totally worth it.
Bootcut and flare jeans are having a moment again, and I’m not mad about it. I got this under $30 pair last year and still love them. The fit through the thighs helps balance out oversized sweaters and jackets, and they look amazing with a heeled boot or chunky platform. Instant long-leg energy.
If comfort is the goal, this pair is the one I’ve been reaching for the most. They have that broken-in feel right out of the box, but the cut still feels modern and pulled together. Perfect with sneakers or a cute flat, just an easy, everyday staple that still feels stylish.
At the end of the day, there are a ton of fun trends to try, but the best jeans are the ones you feel amazing in. These are a few of my current favorites… let me know which style you’re loving most this season!
My Go-To denim retailers
If you’re looking to update your denim this season, these are the spots I always check first. Some are my long-time faves, others are newer finds, but all carry styles I’ve personally worn, loved, and recommended time and time again.
ABERCROMBIE - Great curve styles + modern silhouettes
CHICO’S - Hidden gem for pull-on styles and comfort stretch
GOOD AMERICAN - Inclusive sizing + quality that holds up, my favorite for postpartum, by far!
J.CREW - Classic cuts, trending washes, and petite/tall options
SOFIA VERGARA JEANS (+) - Budget-friendly and size-inclusive at Walmart
SPANX (use CARALYN20) - My go-to for shaping denim with it’s hidden tummy-control panel inside!
honorable mentions:
AMERICAN EAGLE | GAP | J CREW FACTORY | LANE BRYANT (+) |
LEVIS ON AMAZON | WHITE HOUSE BLACK MARKET
Click through to browse their latest arrivals, especially if you’re in the market for a new fit, wash, or rise to love this fall. And if there’s a retailer you swear by that I missed, tell me! I’m always on the hunt for more to try.
JEANS (1X - USE CARALYN15) | SHOP THE LOOK
JEANS (18) | SHOP THE LOOK
Thanks for reading!
Fall denim doesn’t have to be complicated. It’s all about finding silhouettes that feel good, fit your lifestyle, and give you that instant confidence boost when you slip them on. From polished flares to classic black denim and even relaxed jogger-style jeans, there’s truly something for every mood (and every moment) this season.
Which style are you most excited to try, or already living in? Tell me below or shoot me a DM. I love hearing what you’re loving!
xx CMK
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