I went on a little shopping spree last month in anticipation of reaching “immunity” in early May. I looked for a few new pieces and styles that were new to my wardrobe, which was a fun challenge in itself. The pieces were a collection of looser-fitting items, different shapes, and new styles…it was a really fun way to explore the possibilities of my closet. 

Here are four outfits featuring the items I decided to keep! And if after spring and summer I find I wore them a ton, I’ll most likely invest in higher-quality versions of some of these pieces to ensure they last for years to come.

If you didn’t see it before, take a peek at last month’s outfits post, featuring five of my favorite transitional outfits for spring, all styled with the same pair of denim shorts.

Outfit 1: Featuring…pants I could hide my children in (shown above)

I saw someone wearing baggy pants the other day and thought I’d give them another try. I really like these double cloth ones because they have enough structure to not give you a saggy-looking bottom! And they’re so comfy. 

Product Sources: Free People essential doublecloth pants | Mille Florian top, similar here from Free People | & Other Stories straw bucket hat (no longer available, similar here from COS | Free People Delaney fisherman platforms | babaà cardigan (worn in the Instagram reel version of this outfit), similar here from Madewell

Outfit 2: Featuring…sandals I wore in the sixth grade

This outfit features a relaxed and slouchy fit that still feels put together enough for an outdoor dinner with friends. Remember when we wore pants that draped over our shoes?! They’re back!

Product Sources: H&M button-down shirt (low stock), similar here from ASOS | Vintage black denim, similar here from Levi’s | & Other Stories straw bucket hat (no longer available, similar here from COS | & Other Stories Sandals (low stock), similar here from Dr. Martens

Outfit 3: Featuring…my librarian chic vest

This vest was definitely something my heart wanted even before I knew how I wanted to style it. I love it over a t-shirt with shorts and with a billowy top like my absolute ride-or-die fave from Mille. 

Product Sources: Free People Vintage Collection sweater, similar here from Mango | Thrifted Levi’s denim, similar here from Levi’s | Mille Genevieve top | Marion Parke sandals, similar here from TKEES | H&M shorts (worn in the Instagram reel version of this outfit) (no longer available), similar here from H&M

Outfit 4: Featuring…a confidence-boosting dress in a new-to-me shape

I always get at least one new dress in the summer and this one featured a neckline that I hadn’t tried before (see it in action in the Instagram reel!). It is really flattering!!

Product Sources: Maria Stanley cardigan, similar here from & Other Stories | & Other Stories midi dress (sold out in blue), similar here from & Other Stories | Secondhand Totême tote | & Other Stories heeled sandals (low stock), similar here from Chelsea Paris | BAGGU fabric mask | babaà cardigan (worn in the Instagram reel version of this outfit), similar here from Madewell

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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_.