The Millennial Style Academy Vol. 1

Your burning style questions and dilemmas, answered.

Hey Indigoer,

If you’re new here, or maybe you’re a subscriber and never really checked out Instagram, Millennial Mondays is something I started a few years ago as a way to help followers update their closets. When we were all struggling to make the shift from skinny jeans to straight leg jeans, Millennial Mondays was a way for me to show you HOW to make these changes. We also said goodbye to tunic tops, and hello to crop tops (not showing our midriffs though, we’re very demure, very mindful), among other swaps.

I had written this big post about the Millennial style swaps you can make to update your closet. Little tweaks that can make a big impact to make your closet and personal style feel a bit more updated. I then took this to Instagram and started answering questions every other Monday.

It’s been so fun to answer these burning style questions for you. And my favorite part is when I get DMs saying how these posts, and this type of content, have helped you update your closet and just make you feel more stylish again.

Whether you agree or not with saying goodbye to skinny jeans, or any trend in general, and think we should just wear whatever, it doesn’t matter. You do you. It’s not that serious if you don’t want it to be! For me, I think it’s fun to change things up. I enjoy feeling up to date in trends, but also feeling confident in knowing which ones I want to invest in and which ones I’m going to skip. And I hope I can help you do that too with this series.

The one thing I struggle with when I share this content on Instagram is well, I hate sharing on my phone! It’s limited, it’s more time consuming, and it’s just harder. I want to share more images, more collages, more text. But it requires me to sit at my computer, to then share it to my phone, to then find it in my photos to then add it to LTK, and it is a WHOLE thing. Ugh, it’s a struggle. And while I don’t have a seat at the table with Mosseri at Instagram or Amber Venz at LTK who have made creating SO HARD for us desktop girlies, I decided to bring it to Substack.

So yes, I’ll still answer some style questions on Instagram. But the bulk of Millennial Monday is going to live here at Substack. And here’s why I’m pumped for it.

It will live on forever. While you can browse my IG Story highlight (does anyone even do this?), this will live on Substack so you can go back to old posts. My Substack is sort of like another website which is great! They will be more in-depth too with more text and explanation, links to products and collages or photos. These may get cut off in your email inbox, so be sure to click to read the whole thing!

I will collect questions in the comments here at Substack, IG and Facebook. And while this will be content for paid subscribers, there will be a question or two you can see the answers to even if you’re a free subscriber. So you aren’t totally missing out, I promise!

A New Monthly Series For Paid Subscribers

This will become a monthly series that’s more detailed so it is officially time to drop Monday and instead I want to introduce you to, Millennial Style Academy. A destination where you can learn how to update your looks with questions directly from the Indigo community. So with that, let’s dive into your latest questions.

Your Millennial Style Questions

QUESTION: “I struggle with footwear for formal events these days. My days of sky high heels are over, but flats never feel quite fancy enough. What are formal shoes that go easier on my ankles, but are still trendy and cute?”

Answer: I feel like as soon as I hit my mid 30’s the sky high heel game was over. Even more so the moment I moved to NYC. I can’t even imagine dancing the night away in 4-inch heels ever again. There are so many great options for those of us who want to be more comfortable, or are struggling with planter fasciitis (hi that’s me, I’ve hit mid to late 30s and it’s crushing my soul and my body).

Your best bet is going to be one of two options. First, a low heel like a cute kitten heel or a block heel for even more stability. These are so much more comfortable and are super on trend right now. There are so many fun ones too. I’m loving these with the cool silver ankle detail, or these red ones. Mesh detailing is popular across the board and this adds a little something special to these shoes making them feel more appropriate for a special event than just a patent leather. Look for satin, velvet or mesh materials when shopping for a dress shoe.

The second option is a flat like a Mary Jane or ballet flat. Skip the black or nude leather and go for something much dressier like a metallic, a mesh ballet flat or a satin fabric and always embellishments if you can. These leopard bow ones are really fun, and these satin ones from Reformation are nice too. With the mesh trend being so hot right now, these are really easy to find and I think will be a great option to hold on to as your comfy occasion shoes even if they lose their popularity.