3 Outfit Ideas for Summer Gatherings – VERY Affordable, Comfy Clothes for Super Casual to Dressy

3 Outfit Ideas for Summer Gatherings

Huge thanks to JCPenney and ShopStyle for sponsoring this post

Are you in summer planning mode yet? In case you’re gearing up for summer, I’m sharing three outfit ideas for summer gatherings along with some pieces to build your summer wardrobe, and I’m partnering with JCPenney and ShopStyle to do it! Whether you’ll have low-key, casual activities, be enjoying meals with friends, or headed for a summer date, I found some great summer pieces at super affordable prices that I can’t wait to share with you!

I’ve gotta tell you, JCPenney has some amazing finds! They seriously blow my mind sometimes. Whenever I take my friends shopping to rework their wardrobes, I take them to JCPenney because there are so many comfortable clothes like stretchy jeans and stretchy denim shorts, stretchy jackets, great basics, and more, at really, REALLY great prices. Plus, JCPenney offers a wide range of sizing options, including straight/misses, plus, petite, and tall. Also, you can shop online, in store, or shop online and use the free same-day pickup service to grab your order. So, if you want comfortable clothes that are friendly on your wallet, you should definitely look at JCPenney!

In particular, my very favorite brand there is a.n.a, especially for their basics like jeans, shorts, tees, utility jackets, and denim jackets. I have found soft and stretchy options for all of those types of clothes with a.n.a, and to top it off, the pieces average like $6 to $22! Let’s talk through a few worth checking out right now!

SIZING: I’m 5’6″ and usually S/M or 6 in clothes.


Casual Outfit: grey tee + denim bermuda shorts + white slip-on sneakers + white earrings + tan toteCasual Outfit: grey tee + denim bermuda shorts + white sneakers + white earrings + tan tote

Casual: Shorts + Tee + Sneakers
Shorts with a basic tee is a classic laid-back look for super casual, super low-key activities. It’s something I can throw on easily when my kids and I are headed out the door quickly to hang out with friends on a whim.

You guys know I’m always looking for stretchy denim on your behalf, and these Mid Rise 9″ Rolled Cuff Bermuda shorts by a.n.a are worth checking out! They are pretty comfy with a bit of stretch and a worn-in feel. The waistband has a tiny bit of give, while the legs are pretty stretchy and easy to bend and move around in. I imagine they might soften up even more over time with more washes. And, they’re only $14.99 and come in 4 colors! Check them out HERE. I’m wearing the color Light Zodiac in size 6.

In case you’re looking for some basic tees, this Round Neck Short Sleeve T-shirt by a.n.a comes in 8 solid colors and 2 prints, and it is super affordable at $6.74! The rolled sleeves provide extra details that make the tee a little more interesting than a standard basic tee. The scoop neck works with a lot of different kinds of necklaces, if you ever want to dress the tee up a little. And, the tee is long with a scooped hem. I also tried the white version, which has some heather texture so that it’s not as see-through. Check out all the colors HERE. I wear size M.

Shop the Look:
Tee: c/o JCPenney (exact—wearing size M)
Shorts: c/o JCPenney (exact—wearing size 6)
Shoes: (similar)
Bag: (similar)


Nicer Casual Outfit: white yellow ditzy peplum top + denim shorts + tan t-strap sandals + yellow earrings + pendant necklace + tan toteNicer Casual Outfit: white yellow ditzy peplum top + denim shorts + yellow earrings + pendant necklace + tan toteNicer Casual Outfit: white yellow ditzy peplum top + denim shorts + tan t-strap sandals + yellow earrings + pendant necklace + tan tote close up

Nice Casual: Shorts + Nicer Top + Sandals
If you want to step it up from super casual to a nicer casual look, go for a top that has even more details to elevate it from a super casual basic tee. A look like this is great for barbecues, picnics, or a casual lunch out with friends.

This a.n.a V-Neck Short Sleeve T-shirt isn’t a blouseit’s super soft and feels like a t-shirt, but it has more structure and details than a t-shirt with the peplum, flutter sleeves, and print. Having nicer tops that feel like t-shirts is a great way to be really comfortable while dressing up a little! And this one is only $11.24! It also comes in a cute solid light green or sage type of color. Check it out HERE. I wear size S. For reference, it is 22.5″ long from shoulder to hem in size S, so it is on the shorter side.

These Mid-Rise 5″ Denim Shorts from a.n.a are another stretchy, affordable pair of winners to try! I like how distressing on shorts provides more visual interest, but more importantly, this pair is comfy! The legs are really stretchy, and there’s a little give in the waistband. I think these even stretchier and comfier than the Bermuda shorts above. Plus, they’re only $14.99 right now! These have a mid-rise of 9.5″ and an inseam that I measured at 4.5″ (despite them being labeled as 5″). Check them out HERE. I wear size 8. I believe the high-rise version is HERE.

Shop the Look:
Top: c/o JCPenney (exact—wearing size S)
Shorts: c/o JCPenney (exact—wearing size 8)
Sandals: (super similar)
Bag: (similar)

Like I said earlier, almost every pair of a.n.a jeans or denim shorts I’ve tried are stretchy. So, if this pair or the pair of Bermuda shorts don’t work out, I rounded some up for you in the widget below with different rises and inseams. I also included some chino shorts that I tried that were pretty comfortable with stretch, too. Click through the widget below to shop:


Dressy Outfit: pastel striped midi dress + nude wedges + pendant necklace + denim jacket + white bagDressy Outfit: pastel striped midi dress + nude wedges + pendant necklace + white earrings + denim jacket + white bagDressy Outfit: pastel striped midi sleeveless dress + nude wedges + pendant necklace + white earrings + denim jacket + white bag

Summer Date Night: Lightweight Dress + Wedges
Last, dress up a little for a summer date night with a lightweight, summery dress! This a.n.a dress is lightweight with a cute, fresh print for this summer. It is 90% rayon and 10% linen, so it does wrinkle a little with wear, but I generally feel like wrinkles are not as noticeable with prints. There are thick straps to make it bra-friendly along with a flattering empire waistband and adorable button details down the sides. It only $20.99 right now and comes in 3 prints and a solid pale purple/pink HERE.

I’m wearing size S, but the bust is actually a little large for me and I’d want the straps to be a tad shorter for a more snug fit. (For reference, I have a smaller chest and shorter torso, so I think if you’re average in both areas, it’d be fine.) I would either seek to tailor the straps and bust or even try sizing down to XS. This dress is very, very cute! If you have anything to dress up for this summer, I recommend checking this dress out. Just be sure to test it for wrinkling in whatever print you get!

Shop the Look:
Dress: c/o JCPenney (exact—wearing size S)
Jacket: (similar)

Shoes: (similar)
Bag: (similar)

If you’re looking for some more options for summer, check out some of the items in the widget below!



Ready to work on your summer wardrobe?  To help you with summer planning, we’ve got a free checklist for you to download—the Summer Starter Kit Wardrobe checklist!  This is the list of Core Basics from the Summer Starter Kit Wardrobe Guide. Use it to set a great foundation for your summer wardrobe!

Get the free PDF by subscribing to PMT email updates.  Sign up HERE or through the form above and download yours now!

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