Easing Into Fall Outfits | Style Files

Today I am sharing some easing into fall outfits that I hope will give you some ideas for how to transition your summer wardrobe to fall.

Hey friends!  It’s hard to take in that Fall is in full swing, and I’m loving the fall transition in my wardrobe right now!  It’s just plain fun to change things up once in a while, #amiright?  So I thought I would share some easing into fall outfits with you today!  And I’ll also give you some fun tips along the way for layering or adding things to make them even more cozy as fall turns to frigid.

Let’s start with this striped sun dress that I cozied up for fall.  This dress is from Old Navy and I bought it to take to wear during our NYC trip over the summer.  On that trip I wore it with these black sneakers, and I’ve also worn it with cute sandals too.  It’s super easy to transition this dress to fall by adding a cozy cardigan and a pair of booties.  And yes, you can wear booties with dresses!  I’ve had some people tell me that they don’t buy booties because they don’t know how to wear them.  I love wearing them with dresses!I also think this dress is great for fall because of the black striped pattern.  I think virtually any color cardigan would match this dress.

Speaking of booties, I shared some of my favorite booties for fall here.

These booties are about 4 years old and I still love them just as much as the day I bought them.  I remember them feeling like such a splurge to me at the time, but they are just such a basic that I have worn them what seems like a million times.  We should all buy things we love that much!  And these were worth it.

Please note: Some of the links in this post are affiliate links, which allows me to make a small commission from your purchase, but your price stays the same.

To make this outfit or these items a little more cozy as it cools down more, you can easily add a black pair of tights.  These are my most favorite black opaque tights of all time.  A cozy plaid scarf would look great with this, and you can go one step further and add a chambray shirt under the dress if you want too.  That would look super cute! Even a pair of tall boots could work with this dress and cardigan.

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Striped dress  (long sleeve version) | Cardigan | Booties option |

necklace option | Tassel earrings

I am linking to the exact cardigan you see below, but I chose a long sleeve version of this dress because mine is now sold out.  But Old Navy usually always has a version of this dress for every season, and I like the long sleeve version just as much, and it’s still good for layering.  In many cases, I am linking to similar items if the item I am wearing is no longer available.  Using the items I link to will give you a very similar look.

I simply could not resist picking up this cheetah print cardigan when I saw it on Old Navy’s website.  I had a leopard cardigan for a short time that I loved, and I left it at an event in Atlanta.  Never saw it again, and I have always regretted that.  So I scooped this up.  Remember, I use animal print as a neutral, and you should too!

This was a warm fall day in the 80’s, so I was able to wear these cute brown sandals.  But imagine this look with the booties in the outfit above.  I think it would look great this way!  These sandals are very flattering and comfy.  I actually own them in black as well.  And I usually don’t buy more than one color of an item, so the fact that I own these in two colors is proof that they are fab!  This is a classic black sheath dress that has a bit of a cinched in waist.  Any type of black dress like this would create a similar look.  You may have one in your closet right now!

I just threw on this cardigan over it, but I can imagine this cardi over many different solid color dresses.  This Chloe and Isabel tiger eye necklace was a Christmas gift from my husband a couple of years ago, and I love it so much!  I just checked, and it’s currently on final sale for half off, which makes me think they are discontinuing it and I’m sad.  Scoop it up if you like it!  It is convertible and the tassel comes off.

Add some black tights and some booties or pair this cardigan with something else entirely!  It would look great with jeans or a solid colored pair of pants.  It would also look good with a chambray shirt.  You could also pair it with other button down shirts in solid colors.

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Cheetah Cardi | Black dress option | Sandals |  Necklace | Feather cuff bracelet

This next dress is a maxi dress that I just adore!  And good news if you like it, because it is currently on sale for less than $25.  I really love this dress.  It is perfect for summer, but I feel like it can be worn well into fall as well.  I like that this dress is black, because classic!  I also love the fact that the dress has pockets, because who doesn’t love a dress with pockets, it’s a total bonus.  I like the flattering side slits, but they don’t go up too far to reveal too much, so I feel like it is perfect for teachers or similar professions.  There is also a pretty back on this dress, which you can see if you scroll down to the third photo.  This dress is casual and flattering.  It is loose and flowy, and hide a whole lot of evil.  I would definitely wear it with the cheetah cardigan above too.

I wore this dress very recently just as you see it here.  Because we have had a very warm fall so far.  But you can easily cozy this dress up with a cute denim jacket, a chunky cardigan, or a scarf.  I haven’t tried it on with booties yet, but I am imagining that you could throw on a pair of tights with a cute bootie and it would look cool.  I also think it would look cute with a pair of converse or the black sneakers I wore with the striped dress that is pictured above.

Here you can get a glimpse of the back of this dress.  This is really cute for summer, but throw on a jacket or cardigan, and no one is the wiser. I just love the casual vibe of this dress.  i could wear it every day all day.  And if you love it for summer, but not for fall, still do snatch it up, because it is a great price right now.

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Dress | Sandals option  option | Monogram necklace

Do you ever see something while shopping and you instantly know it will be yours?  Well, that is how it went down with this cream colored cardigan.  I was shopping for things to take to NYC, and I simply had to have this cardigan.  I wasn’t even sure if I would pack it to take it to New York, but I knew it was the perfect addition to my wardrobe.  I just feel like this cardigan can work all year around, and it’s super cute with the fringe detail all around the bottom.  I also like the side slits it has.  I did end up taking it to NYC by the way.

Actually now that I am writing this post, I realize that this entire outfit is from Old Navy.  I just love the “Oh Hey Vacay” tee.  You can’t wear it every day, but I don’t work during summer so it’s perfect for summer and fall or even Christmas or spring break.  So I think I will get a fair amount of use out of it.

But the skirt is perfect for all seasons.  I love the olive color and think it is a great color for fall.  It is high waisted and stretchy, but looks like a pencil skirt.  And I can think of so many items in my wardrobe that I can mix and match with it.  And that is my favorite kind of addition to my wardrobe.  If something is versatile, I’m always a fan.

As it gets colder out, these sandals can easily be switched out for a bootie or a tall boot.  I feel that both would look good with this skirt. i even wore it with those same black sneakers around NYC.  I would like to find a pair of olive colored tights because I think they would look great with it.  I also think this skirt would look great with a military jacket or vest.  If you just switched out the tee for a chambray top, and added a tall boot you would have a completely different outfit here.

As for the sweater, it is such a neutral and versatile piece that I can mix and match with so many things I already own.  It would look great with leggings, jeans, dresses, and skirts.  I particularly do love a long cardigan like this with a dress or a skirt.  And you can cozy it up even more by adding a long sleeve top instead of short sleeve.  And it would also look great with a myriad of cozy scarfs.

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Sandals | Plus sized fringe cardigan fringe cardigan option 1 option 2 |

Skirt| necklace option

These are just some ideas I have for easing into fall outfits, and if you struggle at this time of year with what to wear, I hope I gave you some tips that you feel like you can use in your own wardrobe.  I’ll be back tomorrow to share our progress on our kitchen cabinets.  We have painted cabinets!  So I hope you will come back and check that out.  Have a great day!

Before I go, I wanted to mention that I am an Amazon Influencer, and I now have a storefront that is up and running!  You can click here to go to my page.  You will find this smart lock there, along with loads of other things that myself and my family have ordered and love.  I have all sorts of different things linked there, including things that I have already ordered myself and things that are currently on my wish list.

Do you have champagne taste and a tiny budget too? 
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