Fall/Winter Fashion
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5 Easy Ways to Transition Your Outfits From Summer To Fall

Hello Monday! Today is the first day of school for most of the public schools around here, and I have to pinch myself to believe that summer is coming to an end.

Yes, transition season is here, and the question I get asked most this time of year is how to dress for fall when it’s still warm outside. I get it, we’re tired of our sundresses and flip-flops and anxious to bring out our sweaters and booties, but Mother Nature never got the memo that Labor Day is the unofficial start of fall.

There are no “rules” per se these days (don’t put away those white jeans!) but I do try to straddle that warm/cold line by wearing outfits look intentionally Fall but also accommodate the weather.

dress // boots // jacket // bag // necklace

Here are some tips and ideas for how to transition your outfits from Summer to Fall, especially when it’s still warm outside.

How to Transition Your Outfits From Summer To Fall

#1. Wear darker, richer colors. This is not to say that you can’t wear brights or pastels in the fall, but they are no longer my go-to as they are in summertime. Start opting for darker colors in lightweight fabrics and styles that will keep you comfortable but still look like fall.

For example, I wore this burgundy halter top with black jeans and leopard pumps to go on a dinner date with my husband one warm evening last September. The rich, deep color palette says fall, but I was comfortable in the sleeveless top.

similar top // black skinnies // similar pumps

A casual example is this plum colored tee with jeans and grey Converse that I wore to a school event last weekend. Again, it’s perfectly acceptable for summer, but I probably wouldn’t have put this exact outfit together a month ago. It looks more like fall to me.

similar tee // jeans // sneakers // necklace

#2. Throw a cardigan on it! Take any of your favorite shorts-and-t-shirt outfits and add a cardigan, denim jacket, or utility vest. If it’s still hot enough for sandals, stick with brown or something that looks more like fall. Or you can always wear booties for a fun, sassy look.

I wore this outfit one day last fall, and it was fun, but I admit I felt a little over-the-top with the booties. I’m usually more comfortable in sandals or Converse with this look.

cardigan (size down) // tee // similar shorts // similar booties

Here’s one I wore back in July with sandals, but it will actually work just as well in September. I do continue wearing these sand patent sandals into fall, but usually I’ll opt for a darker brown leather like my Lucky Brand Adinis sandals.

cardigan // tee (size up) // similar shorts // sandals

Another option is to throw a denim jacket over shorts and a t-shirt. Swap out your usual sandals for ballet flats to complete the transition look.

similar jacket // similar tee // shorts // leopard flats

And that leads us to #3!

#3. Bring out your booties, ballet flats, and loafers.

I usually put my espadrilles and summery sandals away after Labor Day and bring out my ankle boots and ballet flats. I may still occasionally wear wedge sandals with leather wrapped heels and block heel sandals — especially if they are grey or brown, but I usually opt for more foot coverage. This year’s loafer trend is perfect for in-between weather, especially the ones that are open in the back.

For example, I wore this knit tank dress with sandals last August, but in September I paired it with ankle boots for more of a fall look. Also note how the color says fall, while the sleeveless silhouette is cool and comfortable for warmer fall weather. This would also be cute with a long cardigan or denim jacket on top for cooler fall days.

Here are a few other transitional styling ideas with another sleeveless knit dress. (I clearly have a thing for green dresses!) I love these grey block heel lace-up sandals for a transitional shoe. They’re super comfy too.

tank dress // cardigan // gold sandals // white denim jacket // grey sandals // initial pendant

I posted this look a few weeks ago, and I think it’s a great transitional look. A t-shirt and jeans with espadrilles or strappy sandals says summer, but a t-shirt and jeans with ankle boots says fall!

grey tee // jeans // booties (RESTOCKED!)

And of course, those are colored jeans, but I do this with blue jeans and colored t-shirts as well. I usually opt for a rich fall tone on top like burgundy or plum (see #1) but olive, grey, or white works too.

#4. Switch to darker nail polish. Yes, even changing your nail polish can make your outfits look more like fall. I’m a huge fan of dark blue and burgundy in the fall, but greys and browns are nice too.

This outfit is a good example. I wear this top with light wash jeans all summer long, but simply wearing a darker nail polish on my toes makes it look a little more fall-appropriate. The gold sandals work fine for fall as well, but I might opt for a suede mule next time.

similar top // jeans // similar sandals // tote // sunnies c/o // nail polish

#5. Wear white jeans with fall tops. This is for when weather gets colder, but I love pairing white jeans with earth tones or chunky sweaters and boots once there’s a chill in the air. Take a look at a few of my favorite fall looks with white jeans. In fact, I have a whole post on how to wear white jeans after Labor Day.

sweater // white jeans (option) // plaid scarf // OTK boots

pullover // white jeans (option) // similar satchel // booties c/o Payless // necklace

grey tee // white jeans (option) // similar jacket // booties c/o The Walking Co.

Okay, I know I said 5 tips, but one other thing to consider is your handbag. I have some bags that I carry year ’round and others that I put away for fall and winter. Simply swapping out accessories such as nail colors, shoes, and handbags can take many a summer outfit right into fall without any other adjustments.

I’ll be sharing a lot of fun fall transitional looks in my upcoming 26 Days of Fall Fashion style series where I partner up with Cyndi Spivey over at Grace + Beauty and we each style a new fall outfit every day during the month of September, so stay tuned for that! We start on September 1st.

Before I go, I want to encourage everyone to consider making a donation to Hurricane Harvey relief. I’ve been watching the news out of Texas with a heavy heart. We’ve been having such glorious weather here that it’s hard to imagine how so much flooding and devastation can be happening in other parts of the country, but it’s very real, and many have lost everything. The worst part is, it’s not even over yet.

I like to donate with Samaritan’s Purse, but there are tons of organizations that offer relief for people effected by natural disasters such as this, so pick your favorite and consider what you can give because they’re going to need all the help they can get. No donation is too small; it all adds up.

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37 thoughts on “5 Easy Ways to Transition Your Outfits From Summer To Fall

    1. I know, i always feel that way when there are big news events going on – whether it’s weather related or violence. But there is almost always something bad happening somewhere, and I guess we have to live our lives while trying to be mindful of those in need.

      I feel the same about ankle boots. At first I found them really hard to style, but now it’s coming more easily to me and they seem to go with everything.

  1. LOVE LOVE this post – Fall is my favorite season to dress for and we are already having a dip in temperatures here in Ohio! Great tips!

  2. This is very helpful. Thanks! And I just switched out my polish to a burgundy this weekend. Since I live in MN and we have such a LONG winter, I am waiting to wear any booties or boots until September 1st. My feet have been freezing but I don’t care, that’s all I’ll wear from Sept-March. 🙂 Great ideas for the white jeans too. I have some and I never really know what to wear with them so I have some great ideas now.

    1. I don’t blame you for waiting. I also feel like our summers are too short (not as short as yours, though! Didn’t you have snow in May this year?) and I am probably crazy to go to the booties so soon, but it’s a fun juxtaposition to pair them with shorts and dresses. 🙂

      1. lol, No snow in May by me this year but they probably did in the northern half of the state. I’m near Rochester. A few years ago though we got DUMPED on like May 3rd or something. It was bad….and extremely depressing!

  3. Like you, my heart breaks looking at the pictures from TX. It is more than my mind can comprehend as I am sitting safely on my front porch enjoying the wind and nature. A country singer, Chris Young, is from Houston and has said his home is probably destroyed, but it’s the people that matters. So, he has set up a gofundme page, he’s donating a very large sum of money to the Red Cross, and asking others to join him.
    Love this post and what perfect timing! I bought the camo jeans at ON, along with a mustard colored tee to wear with them, but was wondering about proper shoes, since I think I’m taking it to ATL with us in Thursday. Now, I know what to do!
    Thanks! I hope your ankle is still improving!

    1. Thanks to everyone for thinking of those of us here in southeast Texas. Don’t feel guilty for having thoughts of more pleasant things. We all have a difficult time, at one point or another, thinking of something out of the realm of possibility of where we may be at the moment … human nature I suppose. That said, we will come out of this stronger, and wiser. I’ve lived in this area for 37 years now, and we have weathered Alicia, Allison, Katrina, Rita, Ike, and now Harvey. Trust me when I say, you can’t help but become a stronger, wiser person after seeing and living thru this type of devastation. We will be ok. It’s all just STUFF, after all. PERSPECTIVE …

      1. You have a great attitude, and I hear ya on the stuff, but I remember the months following a major flood in my hometown and the sight of the debris and the stench. It is a lot to live through and takes a long time to rebuild. You all are in my thoughts and prayers. 🙂

    2. Thanks, Ginger. I think it’s fine now. I am so relieved! Still gotta figure out what’s up with my knee, though.

      The camo jeans and mustard tee sound really fun – ankle boots will be perfect with that!

      1. I have the booties for when it gets a little cooler. I have thong sandals with gold medallions on top that I can wear now. I do need to get up in the attic and look for a more appropriate colored purse.

  4. Great post! I love the idea of making outfits more fall-like while still accommodating warm weather (which we typically still have here even after Labor Day). I just bought myself a pair of booties (Ellie was impressed), and I’m excited to pair those with my white jeans to “fall it up”. I’ll wear that with a darker pink sweater for my class tomorrow (I teach on Tuesday, so it’s the one day I wear something other than bad smelling exercise clothes most of the day). And maybe look a little stylish for a change! 🙂 Also, thanks for the plug for TX. I have cousins in Houston, and the pics are terrifying.

  5. I so love that burgundy sleeveless top! I love that you can combine it with pretty much any color to find the perfect Fall colors. And I love the fit, as it seems like it would be forgiving to a lot of body shapes!

  6. Just wanted to share an easy way to donate to the Red Cross: Text HARVEY to 90999. It will prompt you to reply back with “yes” and that will automatically bill your phone bill for $10 to the Red Cross.

    Hope it’s okay to share that here. What’s happening in Houston and all over the gulf areas of Texas is so heartbreaking.

  7. Love this post! Thanks for all of the ideas about how to transform a summer look into a fall one. I have never thought about the color of nail polish. Food for thought.

  8. Love the variety to wearing white jeans into the Fall! I also like the three ways to wear a dress for Fall. In fact I’d enjoying seeing more posts on how to take one article of clothing and wearing it three different ways to create a variety of outfits.
    Praying for Texas.

  9. Love this post! Perfect timing since I won’t have a workwear challenge to participate in, I’m thankful for your help in figuring out what to wear. Love the outfits and ideas. Thank you!!!

  10. I appreciate your fighting the frump tips.
    Updating your makeup, wondering what bands everyone is using. I currently use Merle Norman but my retailer is retiring, no one nearby. I live rural. Looking for input about a new cosmetic line.

    Thx,
    Tessa

  11. Oh Jo Lynne I love how you’ve gone step by step showing everyone. I totally agree about the nail color! It’s such a small thing but I just did mine in dark blue thinking about fall instead of the soft pink I had for summer. It just felt like a natural transition. And I love how you are wearing your white jeans with the OTK boots. So fresh and stylish. I was just thinking about putting my white jeans away mostly b/c I’m kinda sick of wearing them, but you have made me stop and think twice!

    Julia
    http://www.whenthegirlsrule.com

  12. Oops…..when I commented earlier forgot to say how great this post was. I love the striped dress outfit at the front and such helpful hints. I have a hard time going from Summer to Fall especially when Fall weather keeps going on sunny and warm.

  13. I love the way you keep everything so real. I sure appreciate all your hard work it is so helpful! I can’t wait for September 1st So many good ideas here! The small details really bring a outfit up a notch I also enjoy everyone’s comments Praying for everyone

  14. Thanks JoLynne for your thoughts and prayers for my Texas neighbors. We are so fortunate to be just a little ways outside of the storm zone so just got some rain. We will be driving through the Houston area to leave on a cruise out of Galveston next week and I’m already trying to prepare myself; I know what we see on tv doesn’t show the true reality of it all. As far as those impacted by the storm I know they’d appreciate continued prayers.

    1. Thanks for the update, Rebecca. Glad you’ve missed the worst of it. I keep watching the coverage, and I have one friend in Katy who has posted some videos and things – she’s been out helping. It sounds like it will take weeks for the water to even go down. You guys definitely have my prayers. I keep wishing there was more I can do.

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