A Week of Thoughtful Outfits: Early Summer Roundup

Thoughtful Summer Outfits Roundup

Thoughtful Summer Outfits Roundup

Since I haven’t done an outfit post in what feels like forever, I decided to do a roundup of a week’s worth of outfits. As I talked about a couple weeks ago, I’ve been feeling a bit overwhelmed by clothing choices as a result of the aesthetic whiplash we’re experiencing right now in fashion trends.

And it’s been so long since I’ve exercised my outfit-building muscle. After all, I spent most of the last year either working at a hospital or doing school on Zoom. But one thing that has helped me ease back into getting dressed is simply…getting dressed. Actually putting stuff on and wearing it is the best antidote to wardrobe confusion.

These are outfits I actually wore, though I photographed them in one batch after the fact. I have found that taking daily outfit photos takes way more time, so it’s not really worth my effort to do it. Maybe someday I’ll have a dedicated room or space to take photos in.

As a reminder, I am currently shopping according to slow fashion rules rather than taking a strict approach to ethics and sustainability. This process has ensured that I make smarter purchases that work for my body and my lifestyle. I’ve linked to available products, but please keep in mind that they may not be what works best for you.

Day 1: Simple and Bright

Thoughtful Summer Outfits Roundup
Thoughtful Summer Outfits Roundup - Crocs platforms

My definition of simple dressing, but with a bit of a punch. I wore this to go to Outback with Daniel. We greatly enjoyed the Bloomin’ Onion, in case your were wondering.

Top – old J. Crew; Jeans – H&M Conscious; Shoes – Crocs

Day 2: Graduation Picnic

Thoughtful Summer Outfits Roundup

I wore this on a day that was cool in the morning and hot in the afternoon. Daniel and I attended a picnic to celebrate Episcopal student graduates from my seminary. It was so lovely to see the whole group in person after a long year on Zoom.

Top – Loft; Jeans – Banana Republic Factory (they really need to change their name!); Shoes – Camper via Ebay (older style); Cardigan – thrifted

Day 3: Lil’ Backpack

Thoughtful Summer Outfits Roundup - Madewell balloon jeans
Fossil convertible backpack

I talked about this bag in December, but it’s great because you can wear it as a backpack or crossbody. Of course, as with anything with multi-functionality, there are downsides to using it in each position. But it’s still cute and pretty functional. I wore this to trek across campus to pick up a custom sweatshirt, only to be told it wasn’t ready for pickup.

Top – Target; Balloon Jeans – Madewell (reviewed here); Shoes – old Nike; Bag – Fossil (older style)

Day 4: Swoosh

Thoughtful Summer Outfits Roundup - thrifted gingham skirt

My very, very favorite thrifted gingham skirt. It looked almost brown when I bought it because it had been steeped in years of secondhand smoke. But after several washes, it was good as new. I finally bought a pair of Nike high tops I’ve been wanting for a long time. I know I’ll wear them a lot.

Top – old Everlane; Skirt – thrifted; Shoes – Nike Court Royale 2

Day 5: “The biggest little state in the union”

Johnny Was sandals

I got this vintage t-shirt at an antique store when we vacationed in Rhode Island a couple weeks ago (vacationed sounds fancy, but it was just an overnight visit). I paired it with my favorite new cut-offs and sandals I kept even though they arrived with a defect and the company wouldn’t give me a price adjustment. I just loved them too much to part with them.

Top – vintage; Jean Shorts – DIY from these; Sandals – Johnny Was

I spent the last two weeks frantically trying to fix backend errors on the blog, only to create new ones. My apologies if you had a chaotic experience trying to read new posts! The tech team at WordPress are miracle workers.

Let me know if you’d like to see more thoughtful summer outfits roundups! I’ll see what I can do.

Leah Wise

Leah Wise is the founder of StyleWise Blog. She has been writing, speaking, and consulting on sustainable fashion, the fair trade and secondhand supply chain, and digital marketing for over ten years. An Episcopal priest, Leah holds a B.A. in Religion from Florida State University and an M.Div. from Yale Divinity School. When not working, you can find her looking for treasures at the thrift store.

May we recommend...


  1. Seeing others wear REAL clothes, irrespective of what’s “trendy” is always a breath of fresh air to me 🙂 I’m also dipping my toes back into dressing (plus business casual dressing, since I’m no longer WFH) and you’re right that the solution is to just do it!

    1. Thanks! I am pulling my hair out trying to figure out how to do business casual for the internship I start in a couple weeks. But it’s so much easier to do on the job rather than anticipating what I’ll need to wear.

      1. Yes, business casual is the *worst,* mostly because there seems to be little consensus on what is actually IS! I always lean toward overdressing on the first day of a new job and then look at what everyone else is wearing to match the level of formality… Then, when it’s safe, I slowly start dressing more casually, haha. (Because I am not a dressy person.)

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.