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How to Dress Up Shorts for Summer Date Nights

One of my favorite things about spring and summer is outdoor dining. If we’re going out to eat when the weather is warm, and outdoor dining is an option, I’ll usually take it!

But it can be hot if you’re sitting in the sun, so I often wear shorts and dress them up with accessories.

muscle tee (S) // shorts (6) // flip flops c/o (8) // earrings // necklaces one & two // bracelet c/o // crossbody (option) // sunnies (option)

This v-neck muscle tee is a fairly simple top, but the smocked detail on the shoulder makes it a little extra special, so you can dress it up or down.

The 100% cotton fabric has a really nice feel to it, and it’s a versatile 25″ length with a classic fit. It runs true to size and comes in a bunch of colors. It’s also on a really nice sale at LOFT this weekend!

I’ve had these Wit & Wisdom Ab Solution Denim Shorts for a couple of seasons; they’re my go-to for when I want a longer, more polished pair of shorts.

They have a 7″ inseam when cuffed, or you can wear them un-cuffed, if you prefer. They run true to size, and they also come in other colors, if you want something other than white.

A lot of times when we go out to dinner, we have to do a fair amount of walking from the car to the restaurant, so I like to wear more casual shoes. No one wants to see a middle aged mom teetering around in heels on a cobblestone sidewalk!

These flip flops are definitely on the more casual side, but I like the minimalist styling, and they actually have a slightly molded footbed for added comfort.

Up to that point, this is just a basic summer outfit you could wear anywhere from running errands to hanging out with friends. What really makes this outfit pop is the accessories.

This Victoria Emerson Indy Cuff is the first piece I added to the look. I love the mix of animal print, sparkling black crystals, shiny gold chains, and the polished white stone; and the crossover design is different. It really amps up this simple black and white outfit.

Since the top has a deep neckline, I layered two gold chain link necklaces, and I added the oversized rattan earrings for a natural element and keep it summery. I figured I already had enough bling going on!

My black Gucci crossbody seemed like the obvious choice of bag. It’s my go-to for dining out looks when I’m wearing black, and I bring it on most of my trips because it’s so carefree and durable.

I realize it is out of range for many, but there are lots of similar options for less, like the Tory Burch McGraw Camera Bag or the Madewell Transport Camera Bag.

I love how this look came together. I think it’s fun to mix high and low — both with price points and level of formality. But if you wanted to tone it down for everyday, you could just replace the accessories with smaller pieces and a little less bling.

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photos: Live To Adore Photography

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16 Responses

  1. This is a great, simple but perfect outfit, and how I dress most of the summer. Glad you are feeling better and beginning to wear new styles that you couldn’t before. Enjoy!

  2. I love to wear black and white. I’m glad you are feeling better. Excited you are getting to wear different styles!

  3. Cute outfit. So happy for you that you tried on a new swimsuit you like and it fits. You sure must be good at sizing. I have never been able to order a suit. I usually go in store to try. But I haven’t worn one for awhile. 😬Have a great weekend and don’t do too much too soon. Your body has been through a lot. So happy you are feeling ok.

    1. Well, they run XS/S/M/L/XL so that made it easy! I ordered a small and a medium and tried them both. The small fits better, although either would really work, I think.

      Definitely trying not to overdo it, but it is hard to sit still when I’m starting to feel better. 🙂

  4. Cute outfit! I wear shorts to dinner in the summer too. I’ve found that adding wedges dresses it up more than flats, but they’re much easier to walk in vs heels! I love beachy looking ones like Steve Madden’s Uri or Toms Marisol. Also I love linen pants for dinner in the summer. Here in the south you can hardly tolerate regular pants during summer, even at night! But linen makes it do-able and there’s so many fun summer prints that dress them up.

      1. They are tricky! It’s hard to get the fit right, I don’t like the legs too billowy but definitely don’t want them to run tight! I’ve found that I have better look if they’re a darker color or print. More slimming and visually forgiving, plus the inevitable wrinkles are not as noticeable.

  5. This is a perfect elevated casual look. I have not thought to wear my rattan earrings with a bold necklace that is gold, etc., but now that I see how it works, I will. Thank you! I’m glad that you are already able to wear tops that you have not been able too for so long. Prayers for continued healing.

  6. Love your swimsuit!!! I unfortunately was diagnosed with breast cancer in 2018. Went from DD to B. They are not great-uneven, no nipples or sensation, but I like them smaller! Praying you heal quickly!

  7. Good morning,
    I’m so happy your recovery is going well. Some days it does seem like one step forward and two steps back. Most of all I’m glad your are liking how it turned out.
    Quick question…So you like Soma vanishing line or the Bliss cotton panties at Nordstrom?

    Have a speed recovery .❤️‍🩹

    1. Thanks, Missy! The Soma vanishing edge panties are much better at hiding panty lines than the Bliss cotton panties. I wear both – the Bliss cotton to sleep in and often under shorts and things. But when I want a seamless look, I pull out the Soma vanishing ones. I actually just ordered some more b/c I only have the one pair.

  8. I love the longer length white denim shorts. Perfect.

    I wish you’d incorporate more Talbots and Chico’s clothing in your posts. Just Googled styling navy floral denim and one of your 2020 posts came up.

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