Day Dresses + Sneakers

I spend a lot of time crawling Pinterest for outfit inspiration. The truth is that since the pandemic, I’ve struggled with finding my personal style. The number of trends is overwhelming. When you balance that with a changing body and the feeling that my waistline has a mind of its own (I swear, my pant size changes depending on the day!), getting dressed can feel really hard. The Pinterest crawl has been to find outfit inspiration that I find chic, cool (but also comfortable). I’ve noticed I pin a lot of tent dresses and comfy shoes.

One pin in particular (and of course, I can’t find it!!!) really stood out to me. A woman wearing a tent dress (hers was white), colorful necklaces, and pristine white Hokas. Now that, to me, felt like a great everyday outfit. Something I could wear to run errands, but still take a meeting or end up at happy hour. I set out to recreate it with pieces I already had in my closet (I love this Ann Mashburn dress!) and love the result. Comfortable and easy.

Below, I’ve rounded up more great day dresses and sneakers that I think are dress-friendly. This is probably obvious, but to keep this look from getting schlubby, I think your sneakers need to be really clean. So, the sneakers I wear with my dresses are separate from my gym sneakers and/or my yard cleaning sneakers.

PS—Look at this $26 Target dress! It looks so much like the J.Crew one I just bought.

Disclosure: If you buy something through my links, I may earn an affiliate commission at no cost to you. I only feature things I truly love here. Thanks for your support.