Fashion & Beauty

How to Transition Your Favorite Summer Staples into the Fall Season

July 19, 2016

It’s a sad but undeniable truth that summer can’t last forever. The weather will turn cooler, the days will grow shorter, and the leaves will start changing before we know it. And while the start of fall means the end of summer, it doesn’t have to mean the end of your favorite summer clothes. So, before you pack away your go-to warm-weather pieces, try out these quick styling tips that will easily bridge the gap between seasons. 

Perhaps the easiest summer staple to transition into the fall, the sundress only really requires a cozy cardigan and a pair of boots (tights optional) to make it season-appropriate. But if you want to go above and beyond the average transitional outfit, all it takes is a tad more effort—trust us, it’s worth it. Instead of the usual cardigan, try topping your sundress with a chunky knit sweater instead. Not only will you feel super cozy, but wearing something solid over the dress will give the illusion of a skirt-sweater combination, adding to your fall wardrobe options. For an even trendier transitional twist, wear a basic long sleeve shirt or turtleneck underneath your sundress, which works especially well with strappy styles. To tie everything together (and keep you warm), Lyst recommends topping your dress with a more laid-back jacket like a bomber, leather biker, or denim jacket for weekend festivities, or a tailored blazer, which is ideal for the office. 

Rules are made to be broken, especially the one about not wearing white after Labor Day. Sure, white is a crisp and cool hue that we tend to associate with the warmth of summertime, but that doesn’t mean it can’t be worn during other seasons as well. To transition your beloved white skinny jeans from summer to fall, Stitch Fix recommends adding warm textures to your look—think fuzzy sweaters, luxe leathers, rich suedes, and wild knits. As for the color palette, incorporate darker hues on top. They provide a nice contrast to the clean white of your denim, and they’ll add interest and depth to your overall outfit. Finish with a pair of heeled ankle booties and skinnies rolled slightly so that the hem hits right at or a hair above the top of the boot.


An intimidating piece to wear any time of the year, the crop top might seem a little too tricky to rock once the temperature drops, even for the bravest of fashionistas. But if you love this trend during the summer months, chances are you’ll love it even more for fall. The trick to baring your midriff throughout the cooler season is to start with a crop top that hits at just the right spot (your belly button or longer is a good rule of thumb for this). If your favorite summer crop happens to have long sleeves, Style Blazer suggests throwing it on underneath a strappy jumpsuit. And with this trick, you get bonus points for transitioning two summer trends in one go. However, if the style in your closet happens to be sleeveless or strappy, layer it beneath a button-up or an open knit sweater, both of which allow the crop top to peek through while keeping you warm.  

Author Bio: This is a guest post by Nicole Mayer, a freelance writer hailing from Miami who currently resides in New York. In addition to writing about fashion, Nicole enjoys exploring the NYC food scene, visiting with family, and spending Sunday afternoons catching up on her Netflix queue.

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  • Love to wear white during other seasons too, even though it might be more of a challenge it makes a great contrast to the darker colors of fall! Xx

  • I love being able to layer over and under pieces I wear in the summer to keep it interesting in other seasons.

    Amy Ann
    Straight A Style

  • You’ve shared some really great ideas here, girlie! I’m all for transitional pieces and getting the most out of my money! I don’t own a crop top, simply because I haven’t found one that ticked all the right boxes, but I’m still on the hunt and I love the idea if wearing one with longer sleeves over a jumpsuit! I also don’t follow the rule of not wearing white after Labor Day, it’s so ridiculous, isn’t it!? I love the idea of wearing it with warmer and cozier textures to really play up that fall season feel. Great post, beauty, thank so much for sharing and I hope you have a great week ahead!



  • I am all about this… but lol, we won’t be getting fall anytime soon here in Prague. The weather just seems to be getting increasingly hot with each day.

  • Biana Perez

    I love dresses for this exact reason – they are so easy to transition into colder months! xo, Biana

  • I was never a fan of fall growing up in the northeast because it meant winter was coming *shudder*. Now that I live in Florida, I’m not so afraid of fall. We get the fall temps when up north is getting winter, and I love adding jackets to my sundresses and switching out my sandals for some peep toe ankle booties <3
    Green Fashionista

  • These are great tips! I’m trying not to think of cooler temps yet. 🙂 I’m a big fan of layering over summer dresses in the fall.

  • Such great tips! It’s hard to believe fall is creeping up so soon!


  • This is am excellent guest post by Nicole! I love the fashion tips for transitional month! I especially love wearing my maxi dresses under my bomber jacket!

  • What a fun guest post idea and so many great tips! This heat has me wishing for some cooler temps!
    xo, Lily
    Beauty With Lily

  • Love this look! It is always fun to style a summery dress with a cardigan and tights 🙂



    Novelstyle Blog

  • reneejessome

    Great post! Although I’m not quite ready yet to start thinking about Fall!!

    Renee | Life After Lux

  • Emma Cheetham

    Love this post! I love versatile pieces that I can transition through the seasons. You have some great tips. Thanks for sharing!

    Xo, Emma |

  • Jen Dang @ Skirt The Rules

    Ugh, so not ready for fall, but I’m loving your transition tips!

    xo Jen
    Skirt The Rules

  • Charlotte Luisa

    Great tips! I wasn’t even thinking about fall yet but I guess it’s coming quicker than I want it to.. I love pairing girly dresses with a chunky sweater in the winter and fall.
    Love from Boston,
    Charlotte Luisa

  • I love the idea of layering slip dresses over shirts or even turtlenecks for the cooler months!

  • Great tips, Summer has only just started for us here in the UK but it’s never too early to plan the wardrobe. Gemma x

  • Fall will be here before you know it! I love layering over dresses! These are great tips for transitioning!

    Doused In Pink

  • I like the sundress and bomber jacket together! I can’t wait for fall, mainly because of the fashion, football and cooler temps 🙂


  • Ahh mannn….I refuse to believe summer will ever end! haha But it is inevitable. I love just adding a denim or leather jacket to a dress. Great tips!! Thanks!

  • Ianne Cabangon

    These are such nuce transition outfit.
    Xo, Christianne

  • I love the idea of rocking a sweater over a sundress! Great way to continue wearing those pieces through Fall!!

    Allison / Joy and Ivy

  • Great post and tips! Living in Arizona my summer stiff is so drastically different from my winter stuff haha. Not sure they could ever transfer? It actually gets pretty chilly here in the winter (contrary to what people really think), and in the summer ALL I want to wear are jean shorts and anything that pretty much makes me naked lol.


  • Great post! Crop top under a jumpsuit is perfect suggestion! Well , I am thinking of wearing sleeveless waist coat over off the shoulder top and Embroidered jeans…..
    Checkout my recent post here!

  • this post is really useful. You dont have to stop wearing your certain outfits just because of the season


  • Carina Vardie

    I don’t want summer to end, but I love fall fashion. Awesome tips!


  • I love taking summer pieces and making ’em work in the fall- great styling tips, babe!

    Le Stylo Rouge

  • Andreea Birsan

    Mixing summerish pieces into the a/w wardrobe is one of the things that I love doing. Great post babe! x

    Have a nice day,

  • These are great tips Courtney. I sometimes get so frustrated in that gap because I go out super summery and it starts getting cold so I just freeze!

    My Vogue Style |

  • Candace

    Summer pieces are super easy to wear in the fall with layers. Love the slip dress with the bomber. May try this during the fall!

  • Great style inspiration! Love this post , I love wearing summer pieces during fall, the trick is to layer smartly!
    Thank u for sharing this post !

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