
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.
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Hoka Sneakersmy pickThese are very cute and wildly comfortable.Shop
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New Balance SneakersLove this neutral combo.Shop
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Leather Sneakersa sleeker optionIf you don’t want to go chunky, try these!Shop
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Floral MidiThe perfect day dress.Shop
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Suede SneakersI really like this brand (I have a yellow pair) and think the neutrals are really pretty.Shop
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Shell Cutout MidiFrom a local shop here in Charleston.Shop
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Smocked MidiThis is one of my favorite Hill House silhouettes.Shop
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Denim Minieveryday faveI just ordered this. Such a great basic.Shop
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Tie-Waist Maximy dressI love this dress so much. I like wearing it without the sash.Shop
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Button-Back MinifaveI have this in both yellow and white. It’s a great dress!Shop
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Trapeze MiniEasy breezy! I think this one would look great with a chunkier sneakerShop
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Pleated Shirt DressAnother classic fave. I have this in too many versions!Shop
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Striped Maxi$26.00A dead ringer for the striped J.Crew dress!Shop
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Dual-Tone SneakersThe prettiest shade of mintShop
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Patchwork Midiprettiest cutAnother really cute one from Beau and Ro, a local Charleston shop.Shop





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Grace, this is just the content I needed! When I turned 50 my waist expanded about 5 inches and my feet became very problematic. A pretty dress and comfy sneakers are the perfect easy wardrobe formula!!!
The best!!!!! (I have problematic feet as well!) I am glad you enjoyed the post! xx
Why is everyone saying the J Crew yellow dress that you love is very see thru like a beach coverup and runs big . I know if you take a M, I’m definitely a S . I don’t love my weight this low but the white is lined . I like the yellow on you. So cute. Q
I don’t know! I love it. It’s linen which is slightly sheer (the white one is lined) but I”m very happy with mine.