I feel your pain. I never liked casual clothes myself either, for a variety of reasons (lack of structure/ cotton pills easily / lack of petite basics like tees / etc etc etc). But, since we moved, I am in a part of our city which is much more casual, so I've been working on it!
Here's my basic summer capsule for your inspiration:
Because I do like the "3rd layer" and additional structure, but also it gets chilly at night here in the summer.
- White jean jacket (GAP)
- Blue jean jacket (LOFT)
- (not shown) very faded, cropped light blue jean jacket (LOFT)
- (not shown) white linen "army" style jacket (Old Navy)
No shorts. I have one pair of "gear" khaki REI shorts that work in a pinch, but I prefer to keep my legs covered up. No skirts, because they hate me.
- Striped linen high-waisted pants from Anthro
- Silk genie /jogger pants from Anthro
- (not shown) Elephant pants
What's not shown here are basic V-neck tees and scoop tank tops. I prefer Jcrew for tees although I have had luck lately with Madewell. I stocked up on tanks from GAP. I stick to neutral colors - white, grey, black, navy -- to keep it simple.
What is shown are two sleeveless blouses that are actually a part of my business casual uniform, but I could wear them with the green pants if I am going somewhere a bit more dressy. I of course have other sleeveless shells that can work as well.
My favorite item to wear in the summer.
- Tank style Midi & max lengths, similar silouhettes. I found a shape that works and I just duplicate endlessly in different colors/stripes/etc. Most from Old Navy, though there's an older Jcrew one in there as well.
- Waistless A-line dresses (navy with asymmetrical hemline and the denim dress (Anthro, new acquisition)
- Tee shirt dresses (I have same dress in olive and in black) from LOFT or ON
- Pant suit -- for when I want to be more dressy and I could even wear this to work.
- White sneakers
- Flat sandals (in this case Sanuk sling backs)
- Wedge heels
- (not shown) Jcrew metallic thongs, mostly just for the beach/pool
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