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.



Similar outfit

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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.



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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.



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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.


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

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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.


ann taylor bow blouse, sailor jeans, leopard flats

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My Favorite Bags Summer 2022


Medium Transport Tote

(shop more Madewell bags)

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Elpis Woven Straw Handbag

(shop more J.McLaughlin bags)

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Bamboo Handle Rattan Round Bag

(shop more Talbots handbags)


Banya Leather & Paper Straw Tote

(shop more Simon Miller bags)

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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.

Happy Wednesday, ladies!  Really gorgeous weather here in Georgia.  Already got me thinking about the transition from Spring to Summer.  So, I thought I'd do something a bit out of the norm for a Wednesday.  I pulled together 5 comfy casual outfits from our Fridays with Oscar archive that are perfect for that Spring-to-Summer transition.

My long-time readers know that Fridays with Oscar always feature a cocktail and recipe.  I didn't go that far today---have to respect the Friday tradition.  But I did pull together 5 of my favorite healthy eating cookbooks this year as a little something extra.

The Summary

  Today we've got 5 comfy casual outfits for Spring-to-Summer transition

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

  My top 5 healthy eating cookbooks are at the end of the post, so don't miss them!

5 Comfy Casual Outfits

1. Sweater & joggers

Best for those in the low 70s, the first outfit could not be simpler.  A comfy sweater paired with joggers.

Joggers are great for the days when you're lounging around the house.  But dress them up slightly with your favorite Spring sweater and they're also perfect for running errands.

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Similar outfit

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2. Polo & Shorts

We're headed for 80-degree weather here this weekend, so I'm reaching for a pair of shorts.

I'm loving the girlfriend shorts from Talbots this season and they pair perfectly with a simple polo.  I'm keeping the outfit neutral today, but add a pop of color for levity.

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3. Stripe on Stripe

My third outfit is a matchy-matchy stripe-on-strip top and bottom.  I broke up with 'monochrome' with a big dose of color.

I love, love, love pink.  And there's nothing easier than adding color to your outfit with a sweater and your accessory choice.

If pink isn't your color, no problem.  Try yellow, orange, or even a bright green.  Have fun with this one!

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4. Blouse & Jeans

Probably the most "dressy" of the five comfy casual outfits, I went with a print top and jeans here.

So many prints to choose from this year at retailers like Talbots, my similar outfit below features a floral ruffle top.  But swap it out for your favorite, if you're not loving my pick.

And what's so great about this outfit, you could swap out the top for a crisp white button-down or a simple black tee.

So many options here.

Screen Shot 2022-04-20 at 9.46.24 AM

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5. Sweater & Print Pants

My final outfit features a printed pant paired with a simple navy sweater.

Just like the above outfit, there are so many fun printed pants to choose from this year to fit your own personal style.

Keep the sweater simple and just have fun with the pants.  You really can't go wrong.

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The Cookbooks


The Mediterranean Table

Sonoma Press

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Skinnytaste Meal Prep

Gina Homolka


The Comfortable kitchen

Alex Snodgrass

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Well Plated

Eric Clarke


The complete salad cookbook

America's Test Kitchen

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In Case You Missed It

Yesterday, I featured a dress from FARM Rio perfect for any occasion. Click the title or image below to read the article.


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