The Millennial Style Academy Vol. 4 & goodybe to the mid-thigh cardigan

Plus, why I'm not reaching for my classic denim jackets anymore and instead opting for this style instead.

Hi Indigoer!

I’m excited to be diving into our next Millennial Style Academy, featuring a few of my favorite style questions to date. The first question is complimentary, so consider upgrading to paid to unlock the rest of them. Today we’re covering a lot from finding the perfect cardigan that’s updated, my thoughts on the denim jacket, and how to wear sneakers with dresses for 2025. Here’s what’s in this volume of Millennial Style Academy.

• How to wear cardigans

• Where are we shopping for swimsuits

• Are jean jackets still in style and what we’re wearing instead

• What’s the latest in mules

• Making biker shorts outfits cute in the summer

• How to wear sneakers with dresses without looking like we’re in 2015

Let’s dive in!

PS I am running an anniversary special on Substack. My annual plan is currently 40% off and only $30 for the year for LIFE.

*This special promo is only available outside the Substack app so click here if you’re currently reading this on the app. If you’re already a paid subscriber, you can take advantage of this offer by unsubscribing and re-subscribing to reveal the discounted offer. Thank you, as always, for your support here at an indigo day.*

Millennial Style Academy Vol 4

QUESTION: Are jean jackets still in style? What kind are we wearing these days?

ANSWER: Jean jackets will always be in style, but the style of them may vary. Right now, I think the classic jean jacket has been put on the back burner for many. I’m not tossing mine just yet, but I’m definitely not reaching for them much. The jackets I’m reaching for the most, are my cropped utility jacket (featured above) and my cropped trench coat.

The denim jacket styles we are seeing right now are more on the trendy side in terms of silhouette from lady jacket styles, to bombers and cropped denim trenches. If you still have a shrunken denim jacket, I think it’s safe to say you can donate. But for the cropped denim jackets, the oversized ones, I’m keeping those around, but definitely reaching for other jacket styles like cropped trenches and cropped utility jackets.

Row 1 - Lady Jacket • Oversized Utility Jacket • Cropped Utility Jacket

Row 2 - Oversized Denim Jacket • Bomber Denim Jacket • Lady Jacket

Row 3 - Dark Wash Collarless Jacket • Lightwash Shacket • Dark Wash Bomber Jacket

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QUESTION: How are we styling cardigans and what styles are now in?