Outfits Lately | 25 Summer to Fall Outfit Ideas

Good morning Friday!  Every Friday feels so good because that is when I try to take the afternoons to do something fun with my Mom and Jordan, and today we are planning to do some Fall decor shopping at Hobby Lobby.  If that doesn’t get us in the Fall mood, I don’t know what will! I’ve also been trying to dress for fall while it’s still warm out so I wanted to share a round up of summer to fall outfit ideas.

I’m also still on a high from last night’s Project OneWay.  The show was so fun and even though I was so nervous/excited beforehand #jitters!, the wonderful audience put me right at ease and were so great to chat with afterwards.  A million thank you’s to everyone who came out!  I appreciate you so much. I’ll have a recap with pics for you next week!

Our Fitness Challenge is still going strong!  The next Meal Plan will go out in tomorrow’s newsletter, subscribe here so you don’t miss it.

Today, I have a 25 fall outfits ideas to share with you along with some great weekend steals!


5 Weekend Steals Under $35

This racerback dress comes in all kinds of colors, it fits great and it’s only $15! It would look great under a longer cardi or denim jacket for fall.

Any top that comes in a fun, bright color is hard to pass up and the flutter sleeves on this one are so cute! This top is $17 right now, all other tops and sweaters are 30% off too!

This dark green floral dress has me all excited for fall. The $24 price tag is even better! Save 20% off EVERYTHING with code: SWEET.

Save up to 50% on fall faves, like this classic pullover sweater that you can get for $32 in one of 12 colors!

A recent obsession, these Skimmer Jeans in 5 different colors were $68, but now they’re $34! These are the cute little olive colored pants that have the slimming pockets and the butt lift!! #absolutiontechnology


Have you heard the saying, “Dress for the job you want, not the job you have”? As I’m putting together my most recent looks to share with you today, I feel like I’ve been living by the motto “Dress for the season you want, not the weather you have.” It’s been a mix of jeans and fun dresses, plus shorts and sweaters and on a few good days.  We’re truly transitioning to Fall over here.

Outfit Idea #1

Summer to Fall Outfit Ideas

Top • Jeans • Mules • Crossbody

This breezy top is cute with the smocking at the top but loose fitting and comfortable enough to go well with jeans. The color is a great Fall mauve that will look great under a jacket or cardi in a few weeks/months when the temperatures cool off.

Outfit Idea #2

Summer to Fall Outfit Ideas

Floral Top • Frayed Hem Jeans • Booties • Military Jacket • Earrings • Necklace • Lips

Combining Fall + Summer has been a must in Houston and this top is the best of both worlds! This dark floral shell/tank is perfect for hot days, but the dark background with floral print easily lends itself to Fall. It’s silky smooth in the front with a t-shirt material back.  You can give it a mini front tuck for a casual look or tuck it into a skirt or pants for the office.

Outfit Idea #3

Summer to Fall Outfit Ideas

Jeans • Stripe SweaterBooties • Clutch • Bracelet

I got this sweater in the mail and it is giving me all the fall vibes! I love the brown/red/grey combo and paired with the suede booties and clutch #yesplease. Can’t wait to wear this one OUT of the house!

Outfit Idea #4

Summer to Fall Outfit Ideas

Top • Jeans • BootiesNecklace • Bracelet

This is basically just a t-shirt, but the notched neck and the washed-out rust color make it just a little something extra.  And a big yes to the day I got to wear Fall booties!

Outfit Idea #5

Summer to Fall Outfit Ideas

Button Front Dress • Booties • Bag • Necklace • Bracelet

This button front dress had me from the minute I saw it online and I’m so glad it’s as good in person!  With short sleeves and a drop hem, it’s perfect for work to weekend and everything in between.  The relaxed fit is very forgiving and easy to wear.  And, lots of colors to choose from in this one!

Outfit Idea #6

Summer to Fall Outfit Ideas

Top • Jeans •  Heels •  Glasses •  Clutch

I got this peplum top during the Anniversary Sale and it’s just the perfect navy for dressy tops in the Fall. It looks great with jeans, would be killer with a colorful pencil skirt or slacks. I decided on the leopard bag because leopard is a neutral as far as I’m concerned!

Outfit Idea #7

black midi tank dress

Midi Dress • Heels • Similar Clutch • Necklace • Similar Cuff Bracelet

I scored this midi dress for only $42!  It’s double lined to keep you all snug and the midi length is is sleek and slimming.  I noticed sizes were going fast, so this one($56) and this one ($88) are similar options.

Outfit Idea #8

Summer to Fall Outfit Ideas

Lightweight HoodieBoyfriend Shorts • Necklace • Coil Ring

A pullover and shorts has been my outfit of choice recently when I’m just sitting in my office at my computer.  It’s comfy and cozy at the same time.

Outfit Idea #9

Summer to Fall Outfit Ideas

Jeans •  Square Neck Tee •  Wedge Sneakers •  Satchel •  Necklace

My ruffle sleeve top is on sale for only $15 today! ? It’s a super soft knit with a square neck and fun ruffled sleeves.

Outfit Idea #10

Summer to Fall Outfit Ideas

Ruffle Hem Top •  Jeans • Satchel •  Booties •  Necklace

I wore this outfit to the dress rehearsal for Project OneWay.  The thin knit sweater with ruffle trim is perfect for our in-between weather lately.  It’s on sale today 30% off! 

Outfit Idea #11

Summer to Fall Outfit Ideas

Lace Halter Dress XS • Nude Heels

I found your fancy Fall ? dress for a party, dinner out, or wedding! It’s gorgeous crochet, fully lined and fits like a glove! Bonus, it’s under $30 & comes in lots of colors! 

Outfit Idea #12

Summer to Fall Outfit Ideas

Stripe HoodieBoyfriend ShortsSneakers

Jean shorts and a cozy pullover is what I’ve been reaching for while working inside the house and running errands on the weekend.  This striped pullover has a kangaroo pouch and hoodie;)

Outfit Idea #13

Summer to Fall Outfit Ideas

Dress • BootiesEarrings

Happy to share this sweet check dress is on sale for only $37 today (normally $80)! ?? It easily goes from work to weekend and you can style it with heels, a belt, tights, tall boots and/or a leather jacket.

Outfit Idea #14

Summer to Fall Outfit Ideas

Flutter Sleeve Shirt • Jeans • Mules • Crossbody Bag • Sunglasses

The flutter sleeve and criss cross detail at the shoulder of this top is what caught my eye.  It’s super comfy and a step up from your regular v-neck tee. My leopard flats have been on repeat as you can see.  They are so comfy and I love the pop of interest they add to the outfit!

Outfit Idea #15

Summer to Fall Outfit Ideas

Top • Jeans • Purse

I know we’re on the Fitness Challenge now, so this ‘Rose All Day’ top is something to look forward to on that “cheat” day.  I thought it was so cute and a steal at only $12!

Outfit Idea #16

Summer to Fall Outfit Ideas

Floral Maxi Dress

Remember this floral print maxi dress from my first Amazon haul? The colors are perfect for Fall and I felt so feminine and pretty for a girls lunch with my mom and Jordan in it.

Outfit Idea #17

leopard print shirt

Leopard Blouse • Jeans • Heels

Fall is bringing out my love of leopard in a big way!  This leopard blouse is equal parts classic and chic and can be worn casually or dressed up. I like it with jeans and rolled sleeves for a girl’s night out or worn with tailored slacks or a pencil skirt for a smart work look.

Outfit Idea #18

Super Woman tee

Super Woman TeeFave Jean Shorts

Channeling my inner Super Woman here and I have to give credit to James for snapping this pic!

Outfit Idea #19

Summer to Fall Outfit Ideas

Ruffle Sleeve Tee • Frayed Hem Jeans • Leopard Flats • Striped Bag (similar) • Necklace • Similar  Bracelet • Kendra Scott Earrings (30% off)  Military Jacket

I threw on the military jacket to show you how easily it goes with nearly any outfit.  I usually cuff the sleeves by folding them up and then tucking them over the fold for an effortless, unstuffy look. Aren’t those shoes fun?!  I like the pointy toe and they come in both medium and wide widths to fit every foot.

I’m smitten with this ruffle sleeve tee. It’s ultra soft and comfy and the fun sleeve detail dresses it up from your regular black tee.  I like this worn casually with jeans and the pop of leopard, but you could also pair it with a skirt or pants.

Outfit Idea #20

Summer to Fall Outfit Ideas

Colorblock Top  • Scarf • Jeans • Wedge Sneakers • Crossbody Bag • Sunnies • Similar  Bracelet • Earrings

The popular Wedge Sneakers went fast during the Anniversary Sale, but they’re restocked in almost all sizes now!  The zip makes them very easy to get on and off- no laces to mess with.  I think these booties are great for any age and the taupe color is pretty in person. These skinny mini jeans are a mid-rise with a bit of stretch.  I love the medium wash and slight whiskering at the hips.  They also have a comfortable ‘Ab-solution’ powermesh panel to “mold and hold, a waistband with interior control and booty-lift construction.”  #youhadmeatbootylift

Outfit Idea #21

Black boho dress

Baby Doll Dress • Peep Toe Booties

A dead ringer for a Free People dress, but under $25! It’s got darling eyelet detail and the skirt is lined. My 3-strand necklace is restocked in GOLD & on sale too!

Outfit Idea #22

duran duran tee

Duran Duran TeeFave Jean Shorts • Wedge Sneakers

Hungry like the ?! This tee takes me back!  These jean shorts are still in heavy rotation, such a great distressed, relaxed fit and still lots in stock! Wedge sneaks are comfy & cute! 

Outfit Idea #23

Summer to Fall Outfit Ideas

Lace Bell Sleeve Top • Ripped Skinny Jeans • Heels • Round Bali Bag • Kendra Scott Earrings • Rose Gold Watch

This top is one of my absolute favorites and I’ve actually already worn it!  It’s a gorgeous white crochet that is fully lined through the body with a stretchy white underlay.  The bell sleeves are so feminine and pretty.  It looks so expensive and at a retailer like Nordstrom, it would probably be $89.  At Amazon, it’s under $50 and worth every penny!  It also comes in pink and navy and a short sleeve version.

Outfit Idea #24

Summer to Fall Outfit Ideas

Boyfriend Jeans • Cold Shoulder Top • Strapless Bra • Black Heels • Alternative Leopard Bag • Coil Ring

My ‘go to’ look for a girls night out or date night is jeans, heels and a sassy top.  It’s quite effortless, but with the right proportions, it really packs a punch. I’m crazy for this cold shoulder, chiffon number.  It feels beautiful on, but isn’t revealing. The front part is lined and not see-through.  In fact, it’s quite modest with the flowy shape, but showing off your shoulders is so elegant.  I did a mini front tuck to elongate the look of my short legs.

Outfit Idea #25

Summer to Fall Outfit Ideas

Skinny Jeans • Leopard Mule • Leopard Loafers • Criss Cross Sweater • Bralette • Clutch

Anyone else dreaming of Fall?! ? Totally smitten both of these leopard flats that are the perfect transitional Fall shoe. ?? The loafer is a little dressier with a pointy toe and perfect for work, the slide is weekend ready and ultra cute! ? The skinny jeans are a fave budget friendly find! They have special waistline to keep you looking slim and trim! ??

I hope these 25 summer to fall outfit ideas helped you find some creative ways to start dressing for fall while it’s still warm out.

Have a wonderful weekend friends! 

To all of you that are currently in the path of Hurricane Florence, my heart goes out to you and I am keeping you in my prayers.  I hope you and your family stay safe. 

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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!


  1. Bold question here… is your bust “natural” or have you had a boob job? 😉 I’ve always been a stouter build with a large bust; while nursing, not a bra in the world could hold those girls in, and you could tell from across the room…lol! But after nursing my 3 back-to-back littles and finally loosing some weight, my boobs have absolutely shrunk and deflated. I’m horrified as I never in thousand years thought I’d have this problem, and hubby’s a little saddened too. I’ve actually had to gain 15 lbs before they plumped up slightly (but they’re still far from what I’m used to). I figure I’ll take that little extra weight so that I’m not sporting saggy skin boobs…ug! 😛

    1. Hi! I have implants- got them a couple years after James was born and I lost so much fullness after breastfeeding too. I was a natural C and now I’m a D.

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