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Fashion· Summer

Summer Dresses For Every Occasion

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

fit & flare belted sundress

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

Bar III Ruched Tank Dress

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.

striped knit dress

casual weekend style

INC Fisherman Bucket Bag

Bar III Striped Knit Dress

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

City Studios Sundress

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.

vintage-inspired summer style

Fossil Straw Crossbody Bag

fit & flare sundress

classic belted sundress

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

floral maxi dress

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.

summer date night dress

floral print wrap dress

Billabong Wrap Dress

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

OUTDOOR CONCERT

how to style a belt bag

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.

outdoor festival style

Steve Madden Belt Bag

American Rag Printed Dress

Ruffled off-the-shoulder dress

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

Teeze Me Juniors Maxi Dress

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.

INC Bow Clutch

What to wear to a summer wedding

DKNY Floral Statement Earrings

navy maxi dress

What I’m wearing:
c/o Teeze Me Ruffled Maxi Dress, c/o DKNY Floral Earrings,
c/o INC Bow Clutch, Similar Sandals, Lips: Clinique (Hot Tamale)

MORE SUMMER DRESSES

07.25.19 Kimberly

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Penny Pincher Fashion is a part of several affiliate networks. This means when you click on links to various merchants on this site and/or make a purchase, this may result in a commission that is credited to PPF. Also, as an Amazon Associate I earn from qualifying purchases. I take the responsibility of recommending products very seriously & will link to items that I personally love.

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