Six Tips for Transitioning Your Wardrobe to Fall

(Last Updated On: August 8, 2023)

Back in the day when I was full on into my banking career, it was a semi-annual tradition to switch the wardrobe twice a year, as I lived in a very definite four-season climate. Transitioning the wardrobe to fall was an activity that I enjoyed to a point, with the crisp Autumn days, cider mills, bonfires, and other cool weather activities around the corner. Of course, then came winter.

Then I moved to Florida where I lived for twelve years, and the wardrobe was not only very casual, it was warm weather, warm weather, and more warm weather clothes. Pretty simple.

Now that I’m back in the four season climate that wardrobe switch-out is back to a lesser degree, as my in-the-office career days are a thing of the past. But it’s still very much a thing that needs to take place if I want to stay warm and look good in the process!

But it still remains that adjusting your wardrobe to accommodate the fall weather is a task that needs to be accomplished. And, as with so many things that we take on, being organized and purposeful can make all the difference between frustration and feeling victorious (at least for the task at hand!) 

Here are some simple tips for you to make the change easier, so that you’ll look stylish, comfortable, and ready for fall.

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Transitioning Your Wardrobe to Fall

1 | Take an Inventory of Your Summer Clothes First

Before you actually start transitioning your wardrobe to fall and making the switch from the summer clothes to the cooler/colder weather wardrobe, take an inventory of what you have that might need to be washed, dry cleaned, repaired, donated, etc.  

• Use those last days of summer to clean out your closet.  First, you want to get rid of the clothes that have worn out, and are only going to be taking up valuable space in your closet.
• Consider donating these items.  Then, go through what you have left; consider how much use each item has gotten in the past year. Bring them all out (and lay them flat, if possible) so that you can try things on. 
• Once you’ve determined what will be leaving your closet permanently, take stock of the remaining seasonal clothes to see what might need to be washed or dry cleaned. 
• Set aside the cotton and linen dresses, skirt, slacks, and blazers for the next year’s warm season. Then, you’ll be ready to place them in their winter hibernation location, wherever that may be.

2 | Evaluate the Colors in Your Closet

Neutral tones transition well into the fall season.

Dark shades, like deep purples, forest greens, camel browns and navy blues all work well with other fall neutrals: black, taupe and grey.

If your closet is full of bright colors from summer’s fuchsia, lime green and hot pink to light tropical tones, then you’ll want to add some neutrals to the mix.

Are there any animal prints in the wardrobe? These can make wonderful transition pieces…tops, belts, shoes, scarves…they can create a rich look and make a fall fashion statement.

3 | Transition Pieces

There are some wardrobe staples that we can wear as the weather turns cooler. They can be the building blocks of many great outfits.

Wool pants or skirts:   Wool and wool blends are ideal for fall. They warm when it’s cold and breathe when things heat up again in the late afternoon. Plus, they’re great at wicking away moisture so you don’t end up walking around with that damp feeling. 

Why is wool considered a moisture-wicking fabric? We generally equate wool with cold weather, but because the fabric has small openings in it, while it does absorb a small amount of liquid, it also wicks moisture out of those small openings. So, the surface of the wool yarns remain dry to the touch. That’s why it can work well on those warmer fall afternoons. And, these wool styles can carry right into the winter season.

Blazers:    As the temperatures cool, you’re going to need a blazer that can keep up with the changing weather patterns.  Blazers are perfect for throwing on when it’s still hot enough outside and you just want some extra coverage, or if the evening decides to turn chilly. They layer easily over a light sweater or top. 

Fabrics such as tweed or lightweight wool will pair well with jeans and a light colored shirt or top. Be creative in your thoughts about style, too. A traditional blazer is okay, but what about a boyfriend style, slightly oversized, casual blazer? Or a longer length style?

Cardigan Sweaters:   Don’t underestimate how much a cardigan can really spruce up an otherwise simple outfit. It’s the one item that is often overlooked in a wardrobe for women; however, it’s also one of the best secret weapons for fashion.

I love them long and drapey, but there’s more than one way to wear a cardigan! Go with what looks best on your frame and body shape.

Denim: Jeans, skirts, vests, and jackets are favorite go-to’s for a casual fall outfit.

Leather: a lighter weight leather jacket or vest can transform a pair of jeans and top into a fall outfit very easily, and by adding a pair of mules with matching belt and/or bag along with a pair of metallic earrings, you’ve just created an awesome fall outfit.

Find your new favorite blazer or cardigan in this handy LookBook:

4 | Outfit Layering Tips

We may not show our midlife arms to the world like we did in our younger years, but tank tops, sleeveless tops, and short sleeved tops serve an important layering function in the cooler weather.

They add a layer of comfort for the cooler temperatures and serve as a foundation to our fall outfits.

Begin with a short sleeve or sleeveless top, then:

• Wear a button-up shirt over your top, with just one button done, or wear a sweater over the top. It will give you an extra layer of warmth or just a stylish transition from summer to fall.  
• Wear your long-sleeve blouse over the sleeveless top and buttoned up; add a cardigan too, but open enough to display the blouse underneath.
• The longer length cardigan becomes your transitional piece, giving you some extra warmth for the chillier evenings, and it can cover that area of our body that we want to minimize as we get older.
• Take that cardigan and layer it over a lighter fabric dress to create a comfortable fall outfit.

The magic of layering is that you can always add or remove depending on the weather.

5 | Accessories

Accessories are a great way to incorporate fall fashion into your wardrobe because they typically do not add extra layers or warmth, just some cool and interesting style accents.

Bags: The drawstring or cross-body purse is a great fall/winter transition bag. If a larger size suits you better, opt for fall-toned colors like black, tan, or deep green.

Jewelry:  Think rich colors, metallics, feathers and beads.  Other fall jewelry options include beaded necklaces that are unusual and fun, or a chunky bracelet for those cool fall nights.

A woven neckline can be just the right way to incorporate your favorite large necklace into an outfit and still feel that you’re covered for the cooler weather.  Pick one out of woods like cedar, pine, or oak…or even one with a heavier stone like onyx or tiger’s eye. 

Scarves:    From long and draping to small and cozy, scarves add personality to the simplest of outfits.  They are a great way to add the rich fall colors into your wardrobe without being too bold or adding too many layers.

Hats: Are you a hat person? A classic, mid-length wool hat is ideal for both fall and winter.  The caps that we wear in the summer can feel too light when the weather changes; however, a hat that is too short or made of a heavy material can be uncomfortable as the temperatures get cooler and daylight hours decrease. 

Try to choose one in brown or black…two colors that will work for any fall outfit.

6 | Don’t Forget the Shoes

Remember to look at your tootsies, too, when transitioning your wardrobe. Here are some tips for selecting footwear for fall:

Put away the sandals and swap them for a pair of mules. The mules are the perfect transitional shoe because they can be dressed up or down for the season.

A pair of low heeled shoes will elevate the outfit, and you! Your legs will look a little longer when you wear a shoe with a heel.

Or opt for ankle boots paired with leggings or skinny jeans. Boots, and booties, are timeless and look good with fall sweaters and overcoats.

Loafers never go out of style, and they’re a classic for any fall outfit with pants as a foundation.

There are so many styles of flats that will help take your outfit into the cooler weather!

If you still enjoy sandals, like me (I still haven’t gotten accustomed to wearing shoes), opt for darker colors like black, brown, or even tan, to be consistent with both the rest of your outfit as well as the colors of Autumn.

Check out this LookBook for some fall-inspired shoe styles:

Plan Ahead: Create Outfits for your Summer to Fall Wardrobe Transition

Midlife blogger Kay Harms from Dressed for My Day does a fantastic job of demonstrating how to put separates together as the weather begins to cool off.

It’s always helpful and quite a time-saver, to think ahead about the separates in your closet: the pants, denim, tops, sweaters, cardigans, jackets, dresses, and shoes, and how they can work together to carry you through the warm/chilly/hot/cold/sultry/in between days of Autumn.

One method to stay organized is to take the separates and coordinate them in one area of your closet. These will be your ‘summer to fall’ transition outfits.

• place the tops (short sleeves, tanks, 3/4 sleeves, etc) together
• place the long sleeved button up shirts or pullovers together
• place the pants together and organize by fabric or color
• place the outer layering pieces together – the blazers, jackets, cardigans, and sweaters that will carry you through the warm/cool days of early autumn
• place the denim pieces together – jeans, crops, jackets, vests
• place any skirts or dresses that could work as layering pieces together

Now that you have your wardrobe organized for the transition from summer to fall, you can easily put together an outfit by selecting a top/bottom/layering piece from your small collection.

Add the accessories and shoes, and you’re set for whatever the weather will bring you that day!

Conclusion: Transitioning Your Wardrobe to Fall

We know the cooler fall season is around the corner, and before we know it, winter will be upon us. So, why not transition the wardrobe to fall in style? Wearing what we have in different ways, creating new combinations of separates, can almost seem like we’ve gone shopping (without spending a dime!)

Have some fun with your outfits as the seasons changes. It’s a great way to keep a positive outlook and the spirits high even as the temperatures start to drop!

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