How to build your ideal fall wardrobe

I’m back at it…babbling about building your perfect wardrobe.

For some reason, this never gets old for me!  Since you ladies have been asking for my ideal fall wardrobe musings, I’m realizing I am not the only one who is seeking the ultimate wardrobe zen.

I am a big picture person through and through so it seems only natural to start out with what I’m carrying over from spring into fall.  I am a proponent of pieces that work across seasons!  As you know, I believe in investing in quality wardrobe staples that I want to wear all the time!  It is easier to justify spending more when you know you’ll get a ton of wear out of something.

Another point to consider as we reflect on building an ideal fall wardrobe is that this post is part of a series. If  you haven’t already, I highly recommended reading through the previous posts in my ‘Building Your Ideal Wardrobe’ series!  Reading  How to Build Your Ideal Spring Wardrobe part 1 & part 2 will help you get the most out of my wardrobe philosophy as a whole, how pieces carry through multiple seasons, and how to apply this to your own life and preferences!  Think of it as if this were a wardrobe course and the two spring editions are prerequisites.  

Also, most of the pieces I’m featuring here will also make up the bulk of my winter wardrobe with the edition of a few more sweaters, heavier coats, and snow friendly footwear.  As the frigid weather gets closer, I will share a post on what I will add to these staples to carry me  through the harshest New England winter.  And, of course, help you identify what your ideal winter essential list will look like. 

Remember your style vibe and the requirements set forth by your life circumstances may be similar or vastly different from mine.  That’s ok and this editorial can still be very useful for you even if your ideal pieces are entirely different.


Simple adjustments such as swapping out sandals for a fabulous pair of booties, or adding another layer can easily transition a piece from spring to fall.   For example, I would wear this slip dress with sandals and grab a jacket or blazer in case it gets chilly in the spring (or even the summer), and for fall I would add a sweater over the dress & swap out sandals for booties.   Just like that, you’ve got a super chic fall look.

In the spring, I would likely wear a silk blouse on its own with a pencil skirt, trousers or a pair of Levi’s but in the fall I would wear the same blouse under a blazer or a cardigan…or even under my leather jacket for date night. 

 A cashmere sweater is the perfect piece to throw over your shoulders in the spring in case you need another layer, and then for fall it becomes the perfect piece to wear under a light jacket or blazer.

You get the idea, right!?

leather jacket  /  silk slip dress  /  oversized denim jacket  /  oversized v neck sweater  /  black leather booties  /  silk button up  /   black leather belt  /  leather loafers  /  white oxford  /   black blazer


Keep in mind these are my primary essentials for fall.  I don’t really subscribe to the capsule wardrobe philosophy mostly because I know I would get very bored wearing just a small number of items over and over.  I do, however, believe in quality over quantity and in keeping a very meticulously edited closet.  I never have clothes hanging around that I don’t like or don’t wear.  

The building blocks pictured below are first round essentials… or my short list of must haves.  Just as I divided my ideal spring wardrobe into two parts, I would add supplemental pieces to these building blocks to complete my ideal fall/winter wardrobe.  Again, be sure to reread the first two posts in the series.  This post won’t be as useful if you don’t, I promise.  It is the earlier posts in this series that will help you use my essentials as an example to identify and build your ideal wardrobe!  How to Build Your Ideal Spring Wardrobe part 1 & part 2 


wool boyfriend blazer  /  cardigan  /  black turtleneck sweater  /   chunky alpaca sweater  /  black v neck sweater  /  chunky leopard sweater  /  white crew tees /  tank tops  /  sweater dress  /  dress stretch boots  /  leopard belt  /  high rise Levi’s  / high rise black trousers  /   high rise black skinny  /  black leather tote /  combat boots


 In addition to the clothing I carried over from my spring essentials, these are the pieces I do not wish to live without for fall.   Here’s why…

 I have come to value the effortlessness & ease that these pieces provide for me.  My life requires that I easily adapt to changes in plans, and that I am able to get ready quickly and still feel my best.  For me this means that I need to eliminate the extraneous and really hone in on what works best for me… for my style, my body type, my life.  Through trial and error, I’ve learned that I can put on pretty much any combination of these pieces and the outfit will work!  

Jeans and a sweater is probably my most frequently worn outfit formula.  A cozy sweater and an expertly tailored pair of vintage style Levi’s or a fabulous pair of Everlane skinny jeans is what I go to when I don’t have time to think about ironing out the details of a more complicated look.   Changing out shoes, adding a belt…skinny vs. straight leg denim can completely transform a look so that I don’t ever feel like I’m wearing the same thing all the time.  I also love denim paired with a blazer or cardigan with a simple t-shirt or tank underneath.  

An extra long pair of wide leg wool trousers are beyond chic paired with a chunky knit, a straight cut cashmere pullover, a tank top, a blazer, a silk blouse…just about everything I own.  They can be dressed up or down, and…talk about legs for days!

Of course, we all need a stock pile of slim fitting white t-shirts, and tank tops to wear under cardigans, blazers, jackets or even pullovers!  

I firmly believe that if you could only own two dresses…the perfect choices would be a slip dress and a sweater dress.  So effortless, chic and versatile.  Switch up your top layer and shoes, and you can create so many looks.

What does your ideal, effortless fall wardrobe look like?   What pieces would help you feel your best and make getting dressed an easy, stress free event?   Settle in, grab a glass of vino or a cup of coffee/tea and go through the steps I outlined in the first spring edition so that you can determine what this would look like for you.



I absolutely love this view!!

 It is when we look at all the pieces together, that we are able to see what we’ve created.  A workable wardrobe comprised of only pieces we adore that can so easily be remixed to create an abundance of different looks!  Do not be discouraged by the time and patience required to arrive at a closet full of pieces you truly love.  It is a process, but over time you will see it coming to pass.  Yes, money is an obstacle for most (myself included)…and honestly…that is what makes it take soo much time.  I believe the approach I’ve outlined in this series actually saves money in the long run because you are investing in items that you will wear for years to come.  Also, you are carefully choosing pieces that fit your lifestyle, and coordinate exceptionally well with each other.  You have taken the time to identify your style and intentionally choose only what you love.  In doing so you avoid purchasing items you never wear, end up donating…replacing with something else that, again, may not really be right for you.  This is more costly than investing in quality pieces you’ll love for the long haul.

Personal style is an art…one of the very best forms, I believe!  And you are the artist.  Never ever forget you are the artist!!!  


Disclosure:  Some of the links in this post are affiliate links. If you go through them to make a purchase, I may earn a commission.  Please know that I  link these brands and their products because I wear them, use them and believe in them. Not because of the commission I receive from your purchases.  If you do decide to make a purchase, I hope you love it as much as I do and thank you for supporting Diari Di Cuore.


Follow on Instagram

Looking for Something?