15 Ways to Wear Summer Clothes in Fall

I’ve been dreaming about fall and winter clothes for weeks. Visions of fur coats, patterned tights, chunky boots, leather jackets and sparkly holiday dresses dance around in my mind while I’m wearing sandals and t-shirts. Though I can’t stop thinking about fall clothes, the truth is they can get expensive and I still love the things I’ve worn all summer. I hate the idea of packing them away for months and I know there are a million ways to incorporate them into my wardrobe for the cooler months. So, over the next 15 days, I’m going to show you 15 ways to transform things you already have and transition into fall and winter. I’ll list the 15 ideas here, and each day for 15 days, I’ll illustrate one of the tips in my Outfit du Jour and then incorporate a link from this page. I hope it’ll give you a few new ideas for cold weather and be sure to comment with your favorite ways to transition your summer wardrobe into the fall!

1. Add a light jacket.
This might seem obvious, but the potential of a jacket often goes overlooked. Too many times, especially when it’s cool out, jackets are just what we throw on over our outfit while we move from point A to point B. Instead, think of your jacket as an actual part of the outfit, something light enough to leave on throughout the day that adds another dimension to what you’re wearing.
Example: Outfit du Jour: How it Should Be

2. Wear tights.
Tights are one of the easiest ways to take light summer dresses and shorts and transition them into fall. When I was little, I wanted to continue wearing shorts to school even when it got cold in the mornings, so my mom would put bright colored tights under my shorts and send me off to the bus stop. Now, I wear tights all the time. I think you can even wear them when it’s fairly warm out because they are an easy way to highlight colors in your outfit. Pick a less prominent color you’re wearing but that you think is an important aspect of your outfit, and choose tights in that color.
Example: Outfit du Jour: Gold Dust Woman

3. Opt for boots.
Boots are kind of the quintessential fall staple. They’re stylish but often practical parts of a cold-weather wardrobe. There are countless types of boots available and they’re all in style as long as you like them. Pair them with whatever you’re wearing, especially when they are least expected, and you’ll automatically look more appropriately dressed for fall.

Example: Outfit du Jour: I Know What I Know.

4. Wear a flannel shirt.
Almost any short-sleeved shirt can be paired with a flannel shirt for a casual look on a cool day.

Outfit du Jour: My Little Japanese Cigarette Case.

5. Try a turtle neck.
Turtle neck shirts are great because most have long sleeves and they are generally tight-fitting enough to layer under clothes. I wear turtle necks all the time once it gets cold. You can find them pretty cheaply in a variety of colors so that it’s easy to put one under anything to create an extra layer with long sleeves, from t-shirts to dresses.

Example: Outfit du Jour: Swans.

6. Pair bright summer accessories with dark outfits.
Bright accessories leftover from your summer wardrobe are the perfect way to add to a dark, fall outfit.

Example: Outfit du Jour: Think Again.

7. Tailor your accessories and shoes to the weather.

In the summer, it’s easy to wear t-shirts and flip flops for days on end without thinking twice, but as it gets cooler you have to put more thought into what you wear. If it’s raining, try carrying a matching umbrella or wearing galoshes. If it’s really chilly, wear gloves.

Example: Outfit du Jour: Shadow of a Doubt.

8. Try wearing socks with open-toed shoes or even sandals.
For years, wearing socks with sandals has been a faux pas. But not anymore. Cute socks can dress shoes up or down and help transition your favorite summer shoes into fall.

Example: Outfit du Jour: Keep the Car Running.

9. Wear leather.
Warm fall days are the perfect leather jacket weather. If you haven’t worn much leather, you might be under the impression that it’s really warm, but in reality leather doesn’t keep you very warm at all. Try a leather (or faux leather) jacket (or even a skirt) in the early days of fall when you need a light jacket but not a heavy coat.

Example: Outfit du Jour: Mistaken for Strangers.

10. Defer to denim.
Having trouble deciding what to wear? Jeans are always the safe route. Today’s jeans can even be dressy. But remember that denim isn’t just for pants, jean jackets and shirts work with almost any outfit and add an extra layer to your cool-weather look.

Example: Outfit du Jour: Blue Jean Baby.

11. Layer dresses.
Everyone goes layer crazy as the weather cools down, layering shirts, tights and sweaters, but have you ever layered two dresses? Try putting a tight fitting dress with an interesting pattern under a slightly shorter one to give the illusion of a more interesting hemline.

Example: Outfit du Jour: Half of the Time.

12. Play with your maxi dresses.
Maxi dresses have become summer staples but usually get packed away once fall approaches. Instead of forgetting about them for months, try wearing tights or leggings underneath and layering a sweater on top.

Example: Outfit du Jour: See No Evil.

13. Keep your cropped pants.

Cropped pants often seem too summery to wear as the weather cools down, but if you pile on the layers on your top half and pair them with boots or close-toed shoes, they show just the right amount of skin for not-quite-cold weather.

Example: Outfit du Jour: Lately.

14. Have fun with fur.
Nothing says cold weather like fur (or faux fur) but you don’t have to wait until the middle of winter to get your fix. Try layering a fur vest with a quarter-length sleeved shirt or match a fur bag with any of your summery clothes.

Example: Outfit du Jour: Mysteries.

15. Stay warm!
Regardless of what you’re wearing, make sure you stay warm. Pile on layers and don’t be afraid to go all out with the fall and winter accessories. Even if you’re wearing a short dress, it’s okay to wear gloves, scarves and a hat. Chunky winter accessories are cute and practical!

Example: Outfit du Jour: That's It That's all.


  1. Great article! Love the advice for how to use summer pieces in the fall!


  2. Great post! I'll have to keep these tips in mind - and I'm looking forward to seeing your applications of them. I'll have to follow you to be sure I won't miss any! :D

    ~ Katie

  3. Thanks! Today's I'm skipping ahead one idea and wearing open shoes with socks or tights. This is a new one for me too so I'm excited to try it. I'll have an outfit post up later!

  4. This is a great list! Thanks for the advice!

  5. You're very welcome! I'm glad it's been helpful to someone. I know it helped me out to actually sit down and think of ways to make my clothes last all year long!

  6. Okay, I love this post. I am trying to hang on my spring/summer looks as long as possible. I don't want to lose half of my closet! I would love to post this link on my blog sometime this week when I try out some of your tips!