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5 Comfy Casual Outfits For Summer

Happy Friday, ladies!  We’ve made it through another week and are headed straight into Memorial Day Weekend.  We’ve got a fun post for you:  a Fridays With Oscar roundup of 5 comfy casual outfits for Summer.

I went through the archives and pulled together some of my favorite summer outfits, as well as cocktails perfect for a warm summer day.  For each outfit, I pulled together a similar with in-stock items from some of my favorite retailers.  Also, just for something extra, I also pulled together my top 5 handbags for summer.

So sit back and relax:  Oscar, Ollie, and I all wish you a blessed holiday weekend.

The Summary

  Today features 5 comfy casual outfits for Summer

  The outfits I’ve modeled are all old, but I’ve put together similars for each 

  My top 5 handbags for Summer 2022 are at the end of the post, so don’t miss them!

5 Comfy Casual Outfits For Summer

1. Raspberry Mint Mojito Mocktail

My first outfit could not be more simple:  a graphic tee, drawstring pants, and sandals.  Perfect for those lazy Summer days inside and out, you can’t go wrong with a graphic tee.

[GET THE COCKTAIL RECIPE]

FWO-7

Similar outfit

Screen Shot 2022-05-27 at 8.47.05 AM

Board:  “Amour Du Soleil” Crewneck T-Shirt (J.Crew) | The Waist Crop Pants (Talbots) | Printed Canvas Tote (Talbots) | Hanna Vachetta Leather Slides (Talbots)

Shop the Board

2. Old Fashioned

For those early Summer mornings or random 60/70 degree days, pair a sweater and shorts.  Obviously, you can’t go wrong with gingham—and don’t be afraid to pattern (mis)match to add some levity to your outfit.

[GET THE COCKTAIL RECIPE]

DSC09348

Similar Outfit

Screen Shot 2022-05-27 at 9.06.51 AM

Board: Avery Gingham Short Sleeve Shirt (PAIGE, Nordstrom) | Tassel Hem Linen Sweater (Talbots) | Pima French Terry Shorts (Talbots) | Evelynn Wicker Bucket Bag (J.McLaughlin) | Izzy Eyelet Espadrilles (Talbots)

Shop the outfit

3. Red Wine Berry Spritzer

Such a classic pairing:  a clean white midi skirt and a crisp button-down.  I love midi skirts for Summer, and every woman needs a pair of metallic sandals.

[GET THE COCKTAIL RECIPE]

DSC01692

Similar Outfit

Screen Shot 2022-05-27 at 9.16.35 AM

Board:  Ivory Lorna Lace Skirt (Tuckernuck) | Perfect Shirt (Ann Taylor) | Keri Whipstitch Metallica Nappa Sandals (Talbots) | Kara Straw Tote (J.McLaughlin)

Shop the outfit

4. Long Island Iced Tea

Stripes and shorts—a classic summer pairing.  Whether you go with a button-down, tunic, or blouse, blue or red stripes embody Summer.  Pair your shirt with striped sandals for a more put-together look.

[GET THE COCKTAIL RECIPE]

beth from Style at a Certain Age wears a striped shirt, white shorts, sandals, and rattan handbag

Similar Outfit

Screen Shot 2022-05-27 at 9.28.45 AM

Board:  Linen Band Collar Popover (Talbots) | Embroidered Pull On Cotton Voile Shorts (Talbots) | Ilyssa Seersucker Espadrille Sandals (Talbots) | Zip-Top Transport Crossbody (Madewell)

Shop the outfit

5. Gin & Tonic

I definitely don’t shy away from a pair of dark-washed jeans during Summer.  Paired with a neutral blouse, you’ve got a timeless classic look.  And remember, always have a pair of animal print shoes in your closet—they function as a neutral and add visual interest to any outfit.

[GET THE COCKTAIL RECIPE]

ann taylor bow blouse, sailor jeans, leopard flats Screen Shot 2022-05-27 at 9.37.44 AM

Board: Tie Mock Neck Shell (Ann Taylor) | Cindy High Waist Crop Jeans (PAIGE, Nordstrom) | Le Sunset Square Tote Ballet Flat (FRAME, Nordstrom) | Straw Tote (Talbots)

Shop the outfit

My Favorite Bags Summer 2022

1.

Medium Transport Tote

(shop more Madewell bags)

Shop Now Screen Shot 2022-05-27 at 9.44.30 AM Screen Shot 2022-05-27 at 9.46.45 AM

2.

Elpis Woven Straw Handbag

(shop more J.McLaughlin bags)

Shop Now

3.

Ella Canvas Tote

(shop more Tory Burch bags)

Shop Now Screen Shot 2022-05-27 at 9.49.02 AM Screen Shot 2022-05-27 at 9.51.13 AM

4.

Bamboo Handle Rattan Round Bag

(shop more Talbots handbags)

Shop Now

5.

Banya Leather & Paper Straw Tote

(shop more Simon Miller bags)

Shop Now Screen Shot 2022-05-27 at 9.54.40 AM

In Case You Missed It

Yesterday, I shared this year’s Summer Lingerie mega-roundup. Click the title or image below to read the article.

Summer Lingerie 2022 Edition

Screen Shot 2022-05-26 at 2.54.44 PM

About The Author

  1. Marie Dee

    Iโ€™m a huge Oscar fan! His expressions are adorable and he looks so sweetโ€ฆthose little eyebrows! Precious!

  2. Good outfit for the summer
    Bteth specialty for me that live in the beach.
    Thank you

  3. Cute outfits. My favorite is the white shorts, blue and white stripped top and shoes.
    Hope you, Oscar, and Ollie have a very nice
    Memorial Day. Hope you have time with your family also.

  4. Martha

    Greetings to Oscar and thanks for sharing. In Colombia we have a 365-day summer so these ideas come in handy.

    1. MaryLynne

      I have that skirt from Talbot s. I just ordered their embroidered top to go with it. Hope the blues match

Navy Coat winter outfit

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