2 Summer to Fall Outfit Ideas With Loose Denim

Sponsored by J.Crew Factory and Collective Voice

There’s nothing I’m more excited about wearing in the fall than denim.

Not sweaters, not jackets (especially not those since fall where I live is hot), not suede accessories or color-of-the-season accented pieces. Just give me all the summer-to-fall outfits based around cute jeans.

I thought I had tried just about every ’90s style jean on the market, until I spotted the ’90s vintage baggy jean while scrolling through J.Crew Factory’s catalog. It was an easy decision to try these out, but I truly didn’t know just how easily I would obsess over them.

vest (10) | jeans (28) | shoes | bag | scarf | necklace

Summer to Fall Transitional Outfit Ideas from J.Crew Factory

Much of fall fashion trends this season lean decidedly preppy, which makes beloved iconic staples of J.Crew Factory not only a classic favorite, but now an absolute wardrobe score. And because of how affordable their items are, it’s easy to stock up on everything you’re drooling over as we roll into a fresh season (so, uh, yes, I also scooped up their Full Length Wide Leg Jeans to try). Better yet, everything is 50-70% off during their Labor Day Sale event (no code required)!

sweatshirt (XL) | jeans (28) | shoes | necklace

J.Crew Factory does a really good job at stocking a full range of jean styles, from on-trend wide legs to classic straight fits (and flares, and skinnys, and more, too!) but my favorite part is how they offer tall, petite, and curvy fits. As someone who measures 5’10”, I so appreciate the extra length in jeans.

Good denim can be worn a thousand ways, but there’s two specific outfit ideas I’ve been putting into heavy rotation as we transition from the glory beach days of summer to the bustling back-to-school schedules in fall.

Outfit Idea 1: ’90s Vintage Baggy Jeans + The Perfect Vest

The ’90s Vintage Baggy in Clear Light Blue Wash is the perfect light blue loose denim. They nailed the favorite-vintage-jean wash and even got the distressing just right. These are the kind of details that sets the average denim apart from the head-turning pairs – and trust me, this is a pair of jeans that has the IT Factor.

vest (10) | jeans (28) | shoes | bag | scarf | necklace

Fit Notes: I would say they run slightly big, my true size sits a bit lower and loose, but I personally wouldn’t size down. This fit only added to the comfort, while still having a really great bum to them.

J.Crew Factory’s ongoing deals make it easy to try out all the pieces we’re thinking about for the next season – and even the ones we’ve been on the fence about. While grabbing a ’90s style pair of jeans is very run-of-the-mill for me, a VEST?! A vest is definitely not a piece I typically opt for. Yet this one changed my whole plan for my fall wardrobe (I – Am – Not – Even – Exaggerating). 

vest (10) | jeans (28) | shoes | bag | scarf | necklace

If I’m being honest, I mostly avoid sleeveless tops. Showing my full arms is just never where I’ve been the most confident. But I couldn’t help feeling like I was missing out on a really cool trend. Every time I see a vest-and-jeans outfit, I stop and stare. It’s effortlessly cool and incredibly put together. 

I swung for the fences with the Herringbone Button-Front Vest and it completely paid off. I think I stood in front of the mirror for a solid 10 minutes admiring myself in the vest when I first tried it on. I love how the fitted silhouette balances out loose jeans, and yet it still feels gloriously roomy around my soft tumming and arms. I immediately added this look to my “Outfits To Wear On Repeat This Fall” mental list (I may or may not have already repeated the outfit twice…in the same week). 

vest (10) | jeans (28) | shoes | bag | scarf | necklace

Outfit Idea 2: Wide Leg Denim + A Cozy Crewneck

If baggy vintage-inspired jeans aren’t on your fall wishlist (or, like me, you’re looking to add more than one new favorite to your fall wardrobe), don’t skip this full length wide leg jean. 

sweatshirt (XL) | jeans (28) | shoes | necklace

Not only do these come with the supercool, superflattering exposed button fly, but they are made with a bit of stretch to help with all day comfort (which is rad, considering the wash makes them look like rigid raw denim). 

sweatshirt (XL) | jeans (28) | necklace

A dark wash denim tends to have a sophisticated allure about them, which is why I love the juxtaposition of throwing on a comfy crewneck. This 1983 Sweatshirt was a piece I wanted the moment I laid eyes on it. It’s so easy and so cool – the exact kind of pieces I love having on hand to throw on with my jeans when the temperatures dip. This whole outfit feels fresh while being completely comfy for all the busy back-to-school schedules happening around us.

sweatshirt (XL) | jeans (28) | shoes | necklace

Fit Notes: As someone with a very straight, non-curvy frame, there was quite a bit of extra room in the hips and thighs, which makes me think these wide leg jeans could be incredible for all shapes and sizes. They are described as “slim at the hip” but on me these felt quite roomy. I really appreciate the laid back nature of the fit, but if you’re shaped similar to me and seeking a slim silhouette, it would be worth it to try a size down.

 Xx,
Amy

Thank you J.Crew Factory for sponsoring this post! It was SO exciting to get to work with you and highlight my favorite pieces (and if you somehow find more stock of the leopard print mary jane mules that sold out in lightning speed I would be like a little kid on Christmas morning). And to our readers – I mean, if you even got this far to read this end print, I love you forever. Let’s go get coffee and yap about fashion please and thank you. Xxxx

Let’s be friends on Instagram! Sharing life from a California beach town, daily style & beauty faves, and never-ending Taylor Swift dance-athons…all with a good dose of adorable toddler content, too.