17 Super Cute Summer to Fall Outfits

Hey friends!  How’s your week going?! I found myself in school supply HELL yesterday trying to gather ALL the supplies for two grades at the last minute!  I could’ve sworn I ordered the whole packet online ages ago, but when I got the email that they were due for drop off, I realized I hadn’t! 🙁

So, we packed up and went to Target and it’s so hard trying to find all the specific items!  And why did I bring my kids with me who begged for things NOT ON THE SCHOOL SUPPLY LIST!  We are here for SCHOOL SUPPLIES – not toys – people!

At least we found almost everything and it’s really a small thing when you consider the big picture! Maybe I’m a little stressed about school and all.the.things!

17 Super Cute (Summer to Fall) Outfits

I placed an order at one of my favorite boutique retailers, Red Dress, and they have so many cute things!  It’s definitely my go-to when I want to see something new and different for a change.

Everything is on trend, the prices are quite reasonable, and shipping is FREE when you spend $75.

I’ve had great customer service there and returns are super easy too.  *This post isn’t sponsored by Red Dress, it’s just a place I like to shop and think you might too!

This time, I was excited to see lots of clothes I could style for now, while it’s still hot out, and later, when temperatures start to cool off!

For Size Reference: I’m a shorty (5’1) and petite, weighing about 110.  I typically wear size 0p/25 jeans, XS or XSP in tops and dresses.

Jewelry Worn: Crescent NecklaceChokerWrap BraceletBeaded Bracelets

Red Dress Fashion Finds, Tie Dye Crop Top, Shorts, Booties

Tie Dye TopShortsBooties

I’m still super crazy about tie dye, especially when the top is this soft and cozy!  It’s a crop style, but not too short- especially if you’re wearing high waist jeans.  It has a longer, elbow length sleeve that balances out the shorter length.  You can also pull the top to one side and wear it off one shoulder.

Top Fit: I’m wearing a Small

These shorts are so chic and cool, but they do run small.  I ordered my regular size, but wish I would’ve sized up for a more relaxed fit.  I love the light wash, and distressing that’s in just the right places.

Shorts Fit: I’m wearing a 25, prefer 26 since they run small

When you pair a top and jean shorts with booties, it makes it instantly feel Fall foward.

Red Dress Fashion Finds, Tie Dye Top, Jeans Shorts

Tie Dye TopShorts

Red Dress Fashion Finds, Long Sleeve Tee, Jean Shorts, Booties


This pullover top is also so cool with the intricate stitching, long v-neckline, double-slit hemline and dolman sleeves.  It’s perfect for when you want that relaxed, weekend vibe.  I’m wearing the ‘olive’ color, but it also comes in grey and white.

Top Fit: I’m wearing a Small

Shorts Fit: I’m wearing a 25

Red Dress Fashion Finds, Long Sleeve Tee, Jean Shorts, Booties

 TeeAmazon Jeans ShortsBooties

I pulled on my Amazon jean shorts so you could see this outfit with a bit longer jean shorts! These shorts are a longtime fave by Madison and they’re perfectly relaxed with slight distressing and a raw edge hem.

Shorts Fit: I’m wearing a 25

Red Dress Fashion Finds, Sweater, Jeans, Booties


Man, this pullover is SO soft and cozy!  It reminds me of those soft Gibson tops, but this one has a layered neckline and layered cuffs.  It makes it look like you’re wearing a top underneath, but it’s just one shirt.

Pullover Fit: I’m wearing a Small

I got these jeans from Red Dress last year and ‘rediscovered’ them in my closet clean out session.  They were one of the pairs that made the keep list when I gathered up my donations for Star of Hope.  This pair is extremely comfortable with a bit of stretch, a high waist, distressing and a lighter wash.  I’m reaching for them over and over now because they are so comfortable.

Jeans Fit: I sized up to a 3 and they fit perfectly, I’m normally a 0P/25 in jeans

Red Dress Fashion Finds, Sweater, Jeans


Red Dress Fashion Finds, Cable Knit Sweater, Jeans, Mules

SweaterJeansChain Mules

This sweater was in my Loves Giveaway that I announced yesterday!  It’s a mix of crochet front with an almost terry cloth like sleeve.  The sleeves are incredibly soft on the inside and I love how they loosely blouse. But isn’t the contrast fun?!  And the sweater part is mimicked in the sleeve cuff.

The crochet holes are on the bigger side, so you may want to layer a camisole underneath.  I’m wearing my Amazon tank that has skinny adjustable shoulder straps.  They come in a pack of 4 for $24.  They run slightly small, so you may want to size up.

Sweater Fit : Oversized fit, I’m wearing size Small

Red Dress Fashion Finds, Cable Knit Sweater, Jeans, Mules


Romper • Studded Sandals

Of course I love a romper and this one is so comfy/cute! I love the short sleeve style, cuffed sleeve and perfect v-neck.  The waist is smocked with a functional drawstring and it has pockets.  I love throwing this on when I need to run out of the house- it’s a complete outfit without searching for a matching top/bottom.

Romper Fit: Runs small, I’m wearing an XS but I’ll keep it out of the dryer to make sure it doesn’t shrink

Red Dress Fashion Finds, Gray Romper


Red Dress Fashion Finds, Jean Jacket, Romper, Sneakers

Amazon Jean Jacket RomperStudded Sneakers

Come Fall, a jean jacket looks great with almost everything.  This one from Amazon is sturdy and stylish and very well made, being from the Amazon house brand, Daily Ritual.  It’s 98% cotton, with 2% stretch, so it’s easy to wear, but won’t lose it’s shape.  You can find it in three colors, this one is Medium Wash, which looks great with the romper, but also with white or black jeans, skirts and dresses.

Jacket Fit : TTS, I’m wearing XS

Red Dress Fashion FInds, Dress, Booties

DressClear Heels

OMG! This dress is SASSY! I actually adore it for a date night and appreciate how the closed neckline balances the mini skirt.  It’s so short that I’d actually feel more comfortable wearing boy shorts underneath, or with tights in the Fall.  The style is so flirty with the ruffled skirt and ruched tie sleeves.  There’s also a little keyhole tie at the neck that you could also wear open (as seen on the model).

I’m also crazy for the blue and orange floral colors against the dark background.  It definitely makes the dress Fall friendly.

Dress Fit: Runs small, I’m wearing a Small and it’s still short

Red Dress Fashion FInds, Dress, Booties


Red Dress Fashion Finds, Dress, Jacket, Booties, Clutch

DressSimilar Jacket on AmazonBootiesAmazon Clutch

A no-brainer formula for a Fall/Winter night out look is : faux leather jacket + booties = HOT!

Jacket Fit: I’m wearing a Small

Dress Boots

This feminine dress will have you feeling so pretty!  It has a romantic vibe with the floral print and almost sheer (but lined) material.  The ruffles are a sweet touch and it comes with the coordinating tie belt that you could always swap out for one of your own.  Knee high boots look great with this dress.

Dress Fit: I’m wearing a Small


The oranges and browns in this dress lends itself to Fall, but the white background says Summer! It’s a darling little sundress with a tie bodice, flutter sleeves, smocked waist and ruffled skirt.

Dress Fit: I’m wearing a Small

Red Dress Fashion Finds, Dress


Red Dress Fashion Finds, Sweatshirt, Fall Dress, Booties

DressAmazon Pullover • Booties

All you need to do to transition this dress to Fall, is add a sweater over it!  I belted the pullover, then pulled out the top until it looked almost crop length. You can also fold the sleeves and push them up for a more casual look.

Red Dress Fashion Finds, Blue Floral Dress, Wedges


I adored this little A-line dress!  It’s so easy to wear, slipping over your head and being very non-body conscious.  It’s perfect for a big brunch or lunch! And the blue colors are so vibrant and pretty!  Especially with the crochet lined detail.

Dress Fit: I’m wearing a Small

Red Dress Fashion Finds, Blue Floral Dress, Wedges


Red Dress Fashion Finds, Blue Floral Dress, Booties, Jean Jacket

DressJean JacketBooties

Again, simply adding booties and a jean jacket prolongs the life of this dress!  I wore mine this weekend and I’m sure you’ll be seeing it again come Fall.

Red Dress Fashion Finds, Shift Dress, Booties


This dress is similar in shape, but with short sleeves and it’s fully lined.  The fringe part is such a great detail that makes it more special.  I could see adding a colorful scarf if you wanted to add some flair to this outfit for Fall.

Red Dress Fashion Finds, Peasant Dress, Booties


This dress is already quite Fall ready with the autumn “golden brown” color. It feels incredibly smooth and silky on and I like the ruffled/smocked detail at the top, along with the smocked waist and layered skirt.  It’s lined and not at all see-through.

Dress Fit: I’m wearing a Small


Red Dress Fashion Finds, Maxi Dress, Sandals

Maxi DressSandals

Oh man, this dress is going fast so fingers crossed it’s still available in your size!  It’s absolutely stunning in person and very well made.  I was immediately drawn to the classic fit and flare maxi shape and the blue patten with orange ribbon trim.  Sooo pretty! The dress ties at the shoulder and sways gracefully when you walk. It’s also gorgeous in the back with a v/scoop back.

Dress Fit: I’m wearing a size XS

Red Dress Fashion Finds, Black Eyelet Dress, Studded Sandals

Romper DressSandals

Guess what?! This dress is a romper with shorts underneath!  I love that because you get the best of both worlds- it looks like a dress, but has you covered like shorts do.  There is an allover eyelet pattern throughout and a flirty ruffled sleeve.

Dress Fit: I’m wearing a Small

Red Dress Fashion Finds, Black eyelet Dress, Booties, Hat

DressBooties Amazon Hat

Eyelet tends to say Spring & Summer, but with a wool hat and booties, you’re on your way to Fall for sure!  This hat is from Amazon and still going strong after 2 years!  I like that you can adjust the size to fit your head perfectly! And it’s only $16!

shop by clicking the photos below

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Are you still dressing for Summer or is it cooler where you are?  In Houston, we’re watching out for Tropical Storm Laura and Hurricane Marco.  I’m praying we all stay safe, especially our friends in Louisiana, who could take the brunt of it.  ♥

More posts you might enjoy!

Latest Amazon Fashion here & here

Nordstrom vs. Amazon | Looks for Less

In the Dressing Room w Ali-Shaun

My Favorite Meals & Amazon Kitchen Essentials

Painted House Reveal & Fall Decor

Also, don’t forget to subscribe to my blog for a chance to win my Monthly Loves!  And sign up for my FREE printables for our next Fitness Challenge here.  They’ll be live on Saturday, August 29th!


Have a fantastic day friends!


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Meet Megan

Hi! I’m Megan, mom to a thoughtful teenager and spunky young girl. We call Houston home and recently moved into our dream home. I traded my lawyer hat to become a full-time blogger in 2010. I love sharing my passion for affordable fashion, home decor, organization, & fitness to help inspire you to take care of you!

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