I'm Lisa Kirk, a wife, mama, writer, and founder. Since 2010, Something Pretty has been home to my favorite memories, reflections, and inspirations. Thanks so much for reading!

Late Summer Outfit Diary


When my dear friend Emily shared a bunch of my outfit diary photos on her blog recently, I was so encouraged to get this post on my schedule! This late summer outfit diary is a little different than past posts, namely because the outfits I have been most excited by lately have been my forays into “workwear.” I’m now working downtown a few mornings a week, and although I could wear anything to do that, I feel so much better equipped to act and make decisions like the CEO and founder I now am (how wild!) when I’ve dressed the part. If you’re on the hunt for workwear inspiration, I recommend following Kim Le on Instagram. Especially if you work in a corporate/business casual environment and are looking for fresh outfit ideas, she’s an excellent resource!

Since a handful of these pieces are old or “thrifted” (I have been having great luck on Poshmark lately!), I don’t want to focus so much on specific items; I’d rather share the outfit “recipe” you can use for yourself with pieces in your own closet. Of course, if you do have any specific questions about the exact pieces I’m wearing, don’t hesitate to ask!

Tuckernuck Royal Shirt Dress / Margaux The Loafer
I’ve been eyeing Tuckernuck’s array of shirtdresses for ages and finally scooped up this one. Now, I kind of want every color–it just doesn’t get easier to create a polished, comfortable look than throwing on a shirtdress. This one has a very relaxed fit, so it’s comfortable to wear when playing on the floor with the kids too. It does wrinkle easily, but I’ve heard the non-cotton Royal Shirt Dresses don’t. I’m saving up for one and will report back :)

Amour Vert striped tee (similar) / One Third Jacket / J. Crew slip skirt / Margaux The Heel
I mentioned this on Instagram recently, but this cream tweed jacket is one of my FAVORITE new additions to my wardrobe. It’s by a small, female-founded, direct-to-consumer brand that focuses solely on jackets–the easiest “third piece” to add interest to an outfit. I can’t wait to wear it regularly in the season ahead.

Madewell shirt (similar) / J. Crew pants / Sbicca block heels (similar)
I have been wanting a pair of cropped flared pants and bit the bullet on these during a J. Crew sale a few weeks ago. The silhouette has made such a fun, fresh addition to my wardrobe and I’m amazed by how comfortable they are. Definitely recommend!

Lake dress / The Tiny Tassel earrings / Margaux The Demi flats
My Lake pajamas collection is admittedly generous, but this is my first foray into their day dresses. I will say it feels a little pajama-like (unsurprising considering the brand, I suppose!) and runs looser than I would have liked. That said, I got it for a great price and it’s such a classic style. I’m looking forward to trying it with some different layers this fall.

& Other Stories blouse / J. Crew Factory corduroy pants (similar) / Similar captoe slingbacks
This blouse!! I love the color and texture so much. I bought it for an upcoming marketing shoot but haven’t been able to resist wearing it in the meantime…as in, two days in a row this week!

Tuckernuck dress (similar) / Buru belt / Sarah Flint Natalie flats
A midi shirtdress always feels so timeless and polished to me! I’ve worn this look to work and to church, usually with this (stretchy!) raffia belt, but sometimes without.

J. Crew dress (similar) / Mango cardigan (similar) / Veja sneakers
One of my tricks for dressing for fall when it still feels like summer: layer on sweaters without actually wearing them, whether that means looped around your waist or draped over your shoulders. Instant cozy appeal sans sweat!

J. Crew dress / Amour Vert jacket (can’t find anything similar, but this navy cropped jacket is beautiful!) / Sarah Flint Natalie flats
This white denim shift dress was one of my favorite summer buys. I wish it was a touch longer, but still have found plenty of opportunities to wear it. As we’re getting into fall, it’ll be the perfect “blank canvas” for layers.






  1. Em says:

    SO GOOD! And confession: I may or may not have opened up & Other Stories with the intent of buying that shirt after we were together yesterday but they only have size 8 left in stock! Wahhhh! (I’ve decided the only positive of not sitting next to each other every day is that I don’t have to feel bad about owning the same clothing as you, ha!)

  2. Emma says:

    That’s so fun and exciting that you get to work downtown!! The picture you shared on Instagram of your J.Crew beige pants with the mint blazer has been seared into my mind as the epitome of best business outfit, ever!

  3. Dana says:

    So cute!!


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