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Thursday Outfit: Relaxed Date Look

May 22, 2025

After ten years together, our dad nights follow a very specific pattern — the moment the babysitter arrives, run from the house to whatever new bar or restaurant we haven’t had time to try, try to be home by 10:30PM so we can go to bed. So romantic. Welcome to being married with a toddler. But, regardless, I need outfits where I can just change shoes and put on lipstick and leave.

That’s right, it’s Mommy does Day-to-Night. Cosmo would be so proud.

Spotted this look on Pinterest, and I loved the relaxed, casual foundation dressed up for dinner or drinks. The perfect look to just change accessories and hit the town. Let’s remake it.

The Dress // I do not wear silk or satin slip dresses. My postpartum body would need a full shaper to make that look nice, and just, no thanks on that much lycra on a day off. But have a look at this 100% cotton slip dress from Buck Mason, which is a fabulous alternative. And did I mention that it has pockets? Yes, ladies, pockets.

For a similar look in a fuller shape, try this option from Gap. Need wider straps? Try this racerback style from Quince. Plus size? Soma has you covered.

Striped Top // A striped button up top is a summertime MVP. You can wear it as a pool cover, to the office, or layered over a cute dress. Madwell’s oversized shirt is always a great pick. Express has a slightly more refined version with a medium-width stripe for $35.

If you don’t own a striped button up, I recommend buying one. Bring it into your wardrobe, and then, hit up Pinterest for ideas.

The Bag // This clutch from Sezane deserves a moment. I mean, look at this stunning statement piece that is perfect for dressy or casual occasions. *chef’s kiss* Need a less spendy option with the same rope styling? Try this clutch from Nordstrom.

Jewelry & Shoes // I wanted a large hoop for this look, but a basic hoop was not for me. So I decided on these slightly oblong beaded hoop. I also like this larger round beaded hoop. Also, this Madewell cuff is a Tiffany knock-off, and it is a steal.

These shoes are everywhere right now. Quince, as you know, dupes styles from other brands. These strappy kitten sandals are a Khaite dupe, and they’re really comfortable and perfect for summer weddings and events.

Styling // Wearing the hair up is dresses up the look. I’m not usually what I’m going for, so I would wear it down and wavy with a side part and some volume spray. For the makeup, I would transition my daily makeup with some deep raspberry lipstick and a liquid liner.

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  1. Anna says:

    Unrelated-ish…do you have any tips for searching Pinterest or customizing your feed? I recently came back to it after not using it for years – mostly for home decor stuff, but I’d like to use it for hair and fashion too – and it seems like every other pin/post thing is an ad. I wouldn’t even hate this so much if it actually took me to the item, but instead they just take me to an Amazon or Target page with completely different items.

things that caught my eye

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