The past few months, I’ve been trying a different approach to getting dressed. Instead of asking Is this flattering? or Does this go together?, I’ve been asking Do I like how this feels? Do I like how this looks?

I’m reaching for baggy pants, oversized button-downs, sneakers, and maxi dresses—clothes I used to avoid because they weren’t “feminine” or “put-together” enough. Now they’re exactly what I want.

Today I’m sharing a few summer outfit ideas that have felt the most like me lately. Comfy, lived-in, a little offbeat. Dressing for yourself changes everything.

*If an item is no longer available online, I’ve linked a similar product instead (noted below).

5 Summer Outfits I’m Loving This Season

Outfit 1

I wore this on one of those in-between days where it’s hot in the sun but cool in the breeze. This sweater tee reminds me of something I wore on repeat in college. The hat and sunglasses are louder than I usually go, but I love how they shift the whole mood to do not disturb; probably reading.

Product Links

• Denim Shorts – J.Crew
• Montauk Sweater Tee – J.Crew
• Belt – Madewell
• Patent Leather Tote – Sézane (gifted)
• Sunglasses – Monday Swimwear
• Wide Brim Raffia Straw Hat – Janessa Leone
• Multicolored Stone Bead Necklace – no longer available (similar here)
• Pearl Necklace – no longer available (similar here)

Outfit 2

This outfit came together in five seconds and felt easy, but totally different in the best way. I threw the button-down over the dress because I saw “the kids” doing it at the last concert I attended. Now I want to wear this combo every day. It’s simple and unfussy. 

Product Links

• White Tank Dress – no longer available (similar here)
• Yellow Button-Down – no longer available (similar here)
• Black Ballet Flats – no longer available (similar here)
• Patent Leather Tote – Sézane (gifted)
• Pearl Necklace – no longer available (similar here)
• Sunglasses – Teumire

Outfit 3

I love this dress because it’s soft and swingy but structured enough to feel up for taking it out to a party. The flip flops make it casual, and the basket bag makes it feel like I could end up at a market in the South of France… or Target. Which is my reality, but I keep dreaming anyway. 

Product Links

• Dress – J.Crew
• Flip Flops – Havaianas
• Basket Bag – no longer available (similar here)
• Sunglasses – Monday Swimwear
• Pearl Necklace – no longer available (similar here)

Outfit 4

This is what I wear when I want to feel cool but also like I’m in pajamas. I threw this on after a swim, added some layered necklaces, and suddenly it looked intentional.

Product Links

• 2-Piece Set – no longer available (similar here)
• Swimsuit – Monday Swimwear
• Sunglasses – Teumire
• Pearl Necklace – no longer available (similar here)
• Stone/Pearl Drop Necklace – Filosophy
• Silver Phone Case – UEEBAI

Outfit 5

This outfit just made me happy. I started with the pants (bows!), which felt like an outfit in their own right, and kept the top breezy and the accessories summery.

Product Links

• White Button-Down – no longer available (similar here)
• Jeans – Flying Angel
• Woven Bag – Frances Valentine
• Sunglasses – no longer available (similar here)
• Pearl Necklace – no longer available (similar here)
• Multicolored Stone Bead Necklace – no longer available (similar here)
• Flip Flops – Havaianas

Editor’s Note: This article contains affiliate links. Wit & Delight uses affiliate links as a source of revenue to fund business operations and to be less dependent on branded content. Wit & Delight stands behind all product recommendations. Still have questions about these links or our process? Feel free to email us.

Kate Arends

Kate is the founder of Wit & Delight. She is currently learning how to play tennis and is forever testing the boundaries of her creative muscle. Follow her on Instagram at @witanddelight_.