Fashion Transition from Summer to Fall – 4 Key Wardrobe Pieces

Everyone seems to be in transition right now. Kids are heading back to school, my instagram feed is full of pictures of Bento box lunch pails and the latest backpack trends, chalkboards that read, “First day of…” and uncluttered playrooms. The gym childcare is now cleared out of the big kids and now overflowing with all the toddlers left behind by their older siblings, and sadly, our neighborhood pool is closing. Supermarkets are getting decorated with pumpkins and ghoulish Halloween gear, cinnamon brooms and mums. And naturally, Indiana decided now would be a good time to feel like summer, for the first time all summer. What the heehaw?

Now begins the confusing weather patterns, and the teasing of fall. Is she here? Is she coming? Is the heat staying, and will we have one glorious Indian summer until October? Or will I be in a scarf within a week? Nobody can know. But! I am here to tell you, your wardrobe doesn’t need to falter under the weather identity crisis that is a Midwestern September. Here are some strategic pieces that will help you make the fashion transition from summer to fall, while still braving the heat, keep the chill at bay, and do whatever else might be necessary in the uncertain days to come.

Fashion Transition from Summer to Fall – 4 Key Wardrobe Pieces

1. Steve Madden Eros Shoes from Piperlime: Maybe shoes aren’t you first concern. But I like shoes. Especially these. They’re close-toed, so if it gets too chilly, or the ground is full of soggy dew, you won’t have to worry about it. Conversely, if you’re in a pair of shorts and you haven’t painted your toe nails because you assumed the season of sandals would fade with the month of August, these would be your best bet. They’re practical, comfortable, and chic. Wear them with a pair of green chinos, rolled cuff denim jeans, cut off shorts, khaki shorts, or capri pants.

Steve Madden Eros Shoes from Piperlime #fashion

2. Jessica Simpson Pixie Knit Denim Jacket at Macy’s: I am a sucker for a denim jacket. First, you can wear it over everything. A dress, a tank, a tee, a blouse. And this denim jacket with the sweater material on the sleeves looks extra cozy. If it’s unusually brisk, wear it with a black maxi skirt or a pair of  black leggings or black jeans. If it’s warm, but not warm enough, try it with a pair of shorts. I love the idea of layer it with a colorful tank too, because it’s such a good mix of neutrals.

Jessica Simpson Pixie Knit Denim Jacket at Macy's #fashion

3. Pixie Stretch Twill Cropped Pants by Old Navy: I am not going to lie, I really shop at Old Navy most. It’s just close to my house, cheap, and it has a cart where I can trap my son and balloons and coloring tables for my daughter. It just makes sense. And they’ve really been moving up in their fashion choices. I took a rather fashionable friend with me in there the other week and she even seemed pleasantly surprised. That’s right, judge not. And these little cropped pants? Perfect for the weird fall-summer transition. You can wear them with ankle booties, with a pair of sandals, with a wedge, with a pump, with slippers when you need to. Pair it with a sleeveless blouse for warmer days, and top the blouse with a jacket or sweater for the cooler ones.

Pixie Stretch Twill Cropped Pants by Old Navy #fashion

4. Lou & Grey Open Stitch Sweater in Black and White Combo by Loft: I’ve already praised Loft for it’s sales so I won’t go into it, but if the price of this sweater shocks you, just know it will be on sale in a few days. And off sale. And back on. So, Be attentive. Lou & Grey is their new line of clothes that are basically the love child of comfort and chic. I love everything Lou & Grey and you will to. Now this, THIS, is the perfect item to carry in your car. So you showed up at your son’s baseball practice, or your go indoors for your daughter’s gymnastics class, in a tanktop and jeans and you end up cold? Slip on this open stitch sweater, warm enough to insulate, breathable enough to not announce that it’s winter. Or throw it on over a pair of shorts. Or over that same black maxi skirt. Pair it with color. Pair it with neutrals. Just pair it, and bring it with you wherever you go.

Lou & Grey Open Stitch Sweater in Black and White Combo by Loft #fashion

What about you? How do you make the fashion transition from Summer to Fall?

Copyright © Charis Freije, Moms of Faith®, All Rights Reserved


  1. John on September 10, 2014 at 11:49 pm

    Great picks! I always like a lightweight sweater or jacket to transition between summer & fall. Also khakis or chinos seem to work well with both wardrobe seasons.

  2. Ashley Charles on September 14, 2014 at 7:29 pm

    I ran across this post and ordered the snakeskin Vans from Piperlime in the White/Black! I LOVE them! I consider my style to be a bit less “mainstream” and these fit perfectly into my wardrobe! Thanks for sharing!

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