Summer Dresses For Every Occasion - Penny Pincher Fashion

This post is sponsored by Macy’s & ShopStyle.
All opinions are 100% honest & all items were hand-selected by me.

We have officially entered the hottest part of summer and, if you’re like me, the lightest pieces possible are all I want to reach for right now. What I learned while in the 100+ degree weather in India is that dresses are often the coolest option for those sweltering days. Plus, I love the simplicity of just throwing on one piece of clothing & instantly feeling pulled together, regardless of how sticky & miserable I might feel.

Today I’m rounding up the best summer dresses for every occasion in varying styles, silhouettes, colors & prints. Now is a great time to shop because Macy’s just launched a huge sale, where you’ll get an extra 20% off thousands of markdowns when you use code BIG through July 28th! Here are my top picks + full reviews in each category:

CASUAL WEEKEND

Who doesn’t love a comfy, stretchy knit dress that basically feels like you’re wearing pajamas?! This one has such a flattering shape & the ruching detail is very forgiving. I think you could easily dress this up with heeled sandals for date night, but I paired it with a denim jacket & sneakers for an easy on-the-go weekend look. If you’re not a fan of stripes, this also comes in two different shades of gray (links below) – I found this to run true to size, but if you prefer a looser fit, I’d recommend sizing up. Other casual dresses to try: this drawstring-waist dress, this sleeveless knit maxi, this embroidered shift dress and this striped midi.

What I’m wearing:
c/o Bar III Striped Dress (more colors here & here), Similar Denim Jacket,
c/o Converse Sneakers, c/o INC Bucket Bag

SUNDAY BRUNCH

I fell in love with the vintage-inspired design of this sundress – plus, any dress with pockets is a winner in my book! This is fully lined & has adjustable straps – I also think you could remove the belt it comes with & swap it out for a neutral style like this or this. I think this dress is perfect for an afternoon brunch, a bridal or baby shower, a barbeque with friends or dinner al fresco (would also be great to take on any upcoming vacations you may have!).

Juniors’ sizing can be a little tricky to navigate, so if you’re unsure, I recommend checking the size chart on the listing to find your best fit (I’m wearing a size 5 here, which is the equivalent to a women’s 2). I paired it with these classic woven espadrilles that highly resemble the Stuart Weitzman version (but cost a fraction of the price!). More options to try: this printed midi, this white eyelet dress (similar for less here), this gingham sundress, this embroidered shift dress and this tie-front midi.

What I’m wearing:
c/o City Studios Belted Sundress, c/o Enzo Angiolini Wedge Espadrilles,
c/o Fossil Straw Crossbody, c/o Essentials Hoop Earrings

DATE NIGHT

Our kids have finally hit ages where we can leave them at home without a sitter and, this summer, we have taken full advantage of that! We typically go to more laid-back spots that have outdoor seating or hit up the nearest wine bar with light bites. The floral print of this wrap dress is so striking and I love that it’s made from a super lightweight rayon (unlined, but not sheer at all). I did find this to run a bit small, so I recommend sizing up – it is a true wrap style, so if you’re a new mom, it’s definitely nursing-friendly! More date night dresses I love: this ruffled maxi, this snake print dress, this floral print midi and this twist-front slip dress.

What I’m wearing:
c/o Billabong Wrap Dress, Similar Sandals,
Similar Clutch, Nails: Essie (Style Stunner)

OUTDOOR CONCERT

Speaking of date nights, one of our favorite activities to do together as a couple is take in some live music. Even if you’re not a fan of festivals, there are plenty of great outdoor venues where you’ll want to wear something cute & comfortable to fit the setting. This ruffled dress has a slightly bohemian feel to it that makes it perfect for a concert (or the beach!). I added a hands-free belt bag (more colors here) and lace-up sandals with a sturdy block heel (ideal for navigating uneven terrain). I found this dress to run true to size & you can also wear it up on your shoulders (with a regular bra) if you prefer. Other boho-inspired dresses on sale: here, here & here.

What I’m wearing:
c/o American Rag Off-The-Shoulder Dress, c/o Rachel Roy Hoops,
c/o Steve Madden Belt Bag, Similar Sandals

WEDDING GUEST

Since wedding season is in full swing, I had to include this category! I know many of you have multiple weddings to attend, which can get expensive very quickly if you’re having to buy a new dress for each one. Would you believe this navy maxi is under $30? It looks far more expensive & is even more stunning in person. The straps are adjustable & there’s a lace-up detail in back so you can cinch the waist in as much as you want/need to ensure a perfect fit! I added some white accessories & a bold lip for a striking statement. Here are a few more dresses that would be ideal for attending a wedding or special event: this floral lace dress, this colorblocked maxi, this printed midi, this ruffle-trim dress and this floral fit & flare.