Tips to Transform Your Wardrobe From Summer to Fall

Every year when cold weather creeps in, I seem to get stuck in clothing ruts. I throw a black or gray cardigan over my outfit, then put on my well-worn knee high boots and black leggings. I’m not always as creative as I am during the warm weather months. This year, I’m hoping to put an end to the laziness and mix my fall style up a little! I also have so many amazing shirts and dresses that I bought over the summer that I’m not ready to let go of wearing yet. This blog post will be all about transitioning your summer wardrobe into fall by following several simple tips.


    Here is one of my favorite purchases from this summer. I personally love the off-the-shoulder trend, and the vibrant color of this dress immediately caught my eye (I wrote about wearing this top and other brights for summer here). Although today was actually a very hot day, I wanted to style my outfit for fall. When it comes to fall coming, I can be as basic as the next girl! I’m all about pumpkin spice coffee (I tried to avoid it in Wawa, but I couldn’t walk away from that smell), wearing boots, and decorating/planning my costume for Halloween.  This general excitement has definitely translated to my clothing choices lately, and the boots have officially come out to play.  Here are my ideas on how you can transition your summer clothes into fall.

So happy with my new felt floppy hat from Marshall’s!

Summer to Fall Transition Tips

  1. Add a hat to your look. Knit beanies, felt floppy hats, wool cloche hats, berets, fedoras, and leather baseball caps are excellent choices for fall. The key is that cooler weather fabrics are generally heavier than summer hats (such as straw floppy hats or fedoras).
  2. Change up your footwear. In the summer, I typically wore this dress with either block heel sandals, wedges, or slides. As you can see, I switched those out for tan knee-high cowboy boots. Booties, ankle boots, knee-high boots, and oxfords are what I typically wear during the fall months. I am planning on also buying more pumps, mules, and loafers this year for more shoe variety. Keep an eye out for fabrics like leather, brocade, velvet, and wool for shoes. My friend Michelle just got a super cute pair of olive green floral boots that I love! I can’t wait to see how she wears them.
  3. Layer on top of your summer blouses and dresses. Cardigans, blazers, jackets, kimonos, plaid shirts, and scarves transition any outfit easily to fall. Really make sure that you’re not just throwing on the same cardigan with everything, like I was doing! Choose thoughtfully and think about the colors of your outfit. Gray-light pink, tan-orange, ivory-burgundy, navy-dark green, black-red are some of my favorite color combos. The cut of your sweater, shirt, or jacket should also work with the silhouette of your shirt or dress, so that it does not create any odd or unflattering bulges and bumps.
  4. Layer under dresses and skirts with fishnet stockings, leggings, and tights. Nude tights are passe these days, so I would stick to black or another dark color that complements your outfit (I almost always wear black underneath my dresses and skirts.). I think leggings that end at your ankle look best with boots, because it covers up that line between your leggings and skin. This creates a more seamless-and longer-looking leg.
  5. Mix your summer clothes with the Fall 2017 Pantone color collection. These are the most popular colors of the upcoming season. Tawny Port, Butterum, Navy Peony, Neutral Gray, and Autumn Maple can be used as neutrals to mix with your summer wear. I would pair neutral summer clothes with the other colors seen here: Grenadine, Ballet Slipper, Shaded Spruce, Golden Lime, and Marina. I already have quite a few pieces from the past few seasons that I’m excited to bring out again in these shades.


6. Choose heavier fabrics and specific prints to mix with summer pieces. Some examples include leather, lace, animal print, fringe, mesh, fur, suede, brocade, and velvet. I’m not a huge animal print fan unless it’s for shoes or purses…otherwise it feels a little too Peg Bundy for me. I have been lusting after leather skirts and pants. I used to have the best “pleather” pants in middle school, and have wanted a real, grown-up pair of leather pants now that they are back in fashion. I think I could pull them off!

Summer/Fall Mash-Ups

1. New York & Company


Take a cold shoulder dress from summer and pair it with a crop cardigan, fishnet tights, perforated booties, leather satchel, and choker. I layered over top, underneath, switched out shoes, added leather as a fabric, and paired a neutral from summer to a new shade for fall.

2. Ann Taylor Loft


In this look, I took a summer favorite, puffy sleeves in a fall color (Grenadine). I paired it with a leather midi skirt, black tights, loafers, and a gold tassel necklace. I am totally in love with this skirt! I would kill to have it!

3. Gap


My favorite summer pants are my cropped pants from New York & Company! I even bought 2 in different colors (black checks and solid white). Here is an adorable pair of navy cropped chinos, paired with a navy striped top, gray blazer (love the long length), tan leather booties, tan crossbody bag, and navy/red scarf. I usually say no to mixing gray and brown, but the light gray and tan actually look great together!

4. Kohl’s


This look is so cute. I would probably wear it all the time! I’m a big kimono person, and now that I have my floppy hat, I can pair the two together. 🙂

Light pink dresses have been a staple of the summer, and now the fall. A longer, ruffled dress looks wonderful with a kimono of the same or similar length. You could pair a shorter dress with a shorter kimono as well! I chose black leggings (they will go under the gray suede knee-high boots), black felt floppy hat, and multi-tone bangles.


5. Forever 21


Graphic tees don’t go OUT of style in fall, but one cute way to layer it is with a plaid shirt. How amazing is this dark green/black plaid shirt hoodie?? I would wear this all the time! A pair of distressed black skinny jeans, O-Ring hoop earrings, black combat boots, and black quilted backpack complete the look. These backpacks remind me so much of the movie Clueless, and it actually makes me want one more!

I hope you enjoyed this blog post, and that it gave you a few more ideas of how to keep using your summer wardrobe well into the fall! What is your favorite look or tip that you’ve seen here? Do you have any additional tips to help your wardrobe stretch from summer to fall?

Until next time…


49 thoughts on “Tips to Transform Your Wardrobe From Summer to Fall

Add yours

    1. I love oversized cardigans! I used to have a long black one when I was younger that went with so many things. Thanks for commenting!


    1. Thank you so much! You know, we have had some wacky fall weather in Pennsylvania lately. Sometimes it’s still in the 80s in October. 😣


    1. Don’t do anything that doesn’t feel like you! I’m not a scarf person, so I don’t do scarves even though they’re wildly popular.


  1. You make a cute model! Love the floppy hat, too! Funny, I was just thinking today how tired I am with my wardrobe. I could totally wear just about everything you’ve pictured here and nearly every color. About the only color I’m not keen on is lime green – sage would be OK, though.

    Liked by 1 person

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