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Fall 2020 Wardrobe Essentials

September 1, 2020

Welcome to Dressed for My Day, where my goal, each and every day, is to inspire and help women like you and me to dress beautifully and appropriately for our unique days so we can engage authentically and graciously with those around us and influence them well. Yes, it’s a mouthful! Hahaha! But on days like today it bears repeating. It’s Fall 2020 Wardrobe Essentials day!

Fall 2020 Wardrobe Essentials

Wardrobe essentials are the foundational garments and accessories that are absolutely necessary to create the interesting and beautiful outfits you love to wear. At first glance they may seem a little boring. But these pieces are actually the underpinnings of a functional, beautiful and versatile wardrobe. In fact, they’re the glue you need to pull outfits together. So really they’re not boring at all!

Of course, I’m quite aware that my readers are diverse. Some of you gals work outside the home, while others, like me work from your homes. And many others are retired from your professions and enjoying the sweet life (you lucky dogs!).

Of course, as with everything 2020, we have to consider the effects of the pandemic on our wardrobe essentials list, too. You know the ramifications; I don’t need to elaborate. *sigh*

Also, while many of you are here because you gravitate toward my own rather classic style aesthetic, I do know some of you dress more natural and relaxed, feminine, rebellious, creative, dramatic or elegant. So depending on your season of life and lifestyle, coupled with your personal style essence, your fall wardrobe essentials may vary.

Hint: Don’t know your personal style essence? Take my simple, quick What’s Your Style Essence? quiz.

So today’s Fall Wardrobe Essentials list can be interpreted loosely. You don’t need to run out and buy everything on the list. Instead, use my list to help you think about which essentials you may need to purchase or update in order to create beautiful, versatile outfits from the clothes you love to wear.

Let’s get started looking at our fall wardrobe essentials.


Great Denim

As the days get cooler most of us begin to wear our jeans more. And even if you’re still a working gal who dresses more professionally most days, you’ll want some great looking denim to wear for more casual occasions.

AG Farrah High Waist Skinny Jeans

I have grown to love high quality denim, but I don’t think that means you need to dole out hundreds of dollars for every pair. However, I do think, as much as most of us wear our jeans, it is important to have at least a couple of pairs that fit and flatter you beautifully.

Flare Crop Jeans In Authentic Mid Indigo Wash
Loft Flare Crop Jeans In Authentic Mid Indigo Wash

This year skinny jeans and boot cut jeans are still fashionable, but straight leg jeans have taken the lead. Right now we’re seeing mostly cropped or ankle length straight cut jeans, but I imagine we’ll be seeing longer lengths with cooler weather.

Loft Destructed High Rise Straight Crop Jeans

We’re also still seeing lots of deconstructed or ripped jeans. And raw or even chewed hemlines continue to trend. But don’t worry. If these rough and rugged touches aren’t your jam, you can also wear pristine denim and look very in style and chic.

Talbots Denim Jegging Rinse Wash

Also trending are high-rise jeans. That’s great news for most of us gals who need to tuck away some rolls, ahem. Gals, get you some high-rise jeans. They are definitely the most flattering, even if you are short waisted. If you do have a short torso, just don’t tuck your shirt into high-waist or high-rise jeans. High-rise jeans are those that hit you right at your navel or just below. I suggest looking for jeans with a rise of 9.5″ – 10.5″. Anything higher than that might be considered super high rise and those tend to be less comfortable to me.

For each wardrobe essential I’m providing a shopping widget with a price and style variety of that essential. These are affiliate links, so if you shop through them and buy something I do earn a small commission, but at no additional cost to you. Thank you so much for shopping my links and supporting what I do here.

Solid Pants in Neutral

While I tend to wear jeans most days, I also like to have other pants in my wardrobe, both for dressier occasions and variety’s sake. If you’re a working gal you may want more, but even if your lifestyle is rather casual I suggest having at least one pair of other pants, preferably in your personal wardrobe neutral shades (see this post for determining your wardrobe colors).

Nic+Zoe Wonderstretch Straight Leg Pants

I own the black pants in the photo above. They are a little pricey, but I’ve had them for three years and I’ll be wearing them for years to come. I’ve already tried them on recently and they still look great. In fact, I can’t wait to start wearing them again. So no new black slacks for me! That’s the beauty of buying high quality, classic wardrobe essentials. PLUS right now these pants are 25% off.

I’ve mostly included pants that I’ve tried and liked in the shopping widget below. I can also highly recommend these pull-on signature slimming luxe stretch pants from Christopher & Banks. They’re with a different affiliate network, so they’re not included in the shopping widget below.



You’ll find t-shirts in all of my wardrobe essentials lists. In fact, t-shirts are year-round essentials in my book.

Summertime Uniform with Jeans
Mott & Bow Marcy fitted crewneck T-Shirt

While I still keep my short sleeve tees accessible during the fall and often wear them, I do like to have a good selection of 3/4 length and long sleeve tees in my fall wardrobe. I suggest you have several good, comfortable and well fitting long sleeve or 3/4 length sleeve t-shirts in neutrals like white, off white, grey or black.

black t-shirt
My Favorite T-Shirt: Banana Republic Supima Cotton V-Neck

Hint: We’ll talk about colors and prints next week when I share how to create a capsule wardrobe that works with your wardrobe essentials.

Do your wardrobe essential tees have to be basic crew or v-neck? No. No, they do not. Choose wardrobe essentials that reflect your personal style and that will work with versatility in your personal wardrobe. The puff sleeve tee is very on trend and would reflect a romantic personal style aesthetic among others.

Pima Cotton Puff Sleeve Top

These are the shirts you’ll be wearing often under your favorite cardigans, pullover sweaters or jackets, so choose accordingly. I still think v-necks are the most universally flattering neckline for women, but scoop, bateau neck and crew neck tees serve their purpose, too.

Chambray Shirt

Chambray shirts also make my year-round essentials list. Of course, the length of sleeves changes with the seasons. If you don’t already have a long-sleeve chambray or lightweight denim shirt in your closet, now is a great time to look for one.

Talbots Button Front Denim shirt

A chambray shirt is such a versatile piece. You can dress it down with jeans or other casual pants, such as cargos. But you can also pair it with a pretty pencil skirt or dressier slacks for the office or church. Adding a chambray shirt is also a great way to wear white jeans into the fall and winter.

Statement Blouse

I think it’s smart for every gal to also have a pretty statement blouse at the ready. Depending on your style aesthetic, this could be a silk blouse or a cotton one, polyester or a blend. And while I think a solid is your best bet, you could opt for a pretty floral or other pattern, too. You just want this one blouse to be extremely versatile, pairing easily with many of your jeans, skirts and pants.

Silk Blouse
Silk Shirred v-neck Blouse

Completer Pieces

Let’s hear it for completer pieces!!! Yay! Great outer layers are one of my top 5 favorite things about fall, right in there with pumpkin spice lattes, apple picking, colorful leaves and candy corn. I suggest you consider three completer pieces as wardrobe essentials.


Admittedly, I gravitate toward cardigans this time of year. I just love the yummy, soft texture, the warmth and the sleek, sophisticated presentation of a stylish cardigan. This year, dusters or long cardigans are still trending. But I think the mid length that hits just below the hip has made a resurgence to the top of the list.

Blush Blouse + Black Jeans 3 Ways
Wool & Cashmere Long Cardigan

When selecting a cardigan to serve as a wardrobe essential, I suggest looking for one in a neutral that works well with your other clothing. Also watch for pocket placement. I try to steer clear of patch pockets on the hips.

Denim Jacket

I guess if you live in a cool climate (like I do…now!), you wouldn’t necessarily wear a denim jacket much in the winter, but otherwise it’s a year-round staple. I suggest investing in a timeless, fitted blue denim jacket. But after that, the sky’s the limit! You can also look for jackets with cinched waistbands, softer silhouettes and in different colors or patterns.

denim jacket
Levi’s Original Trucker Denim Jacket in Sweet Jane for less than $50


Blazers were set to trend high again this year. But since many of us are going out a good bit less, I don’t think we’ll get as much wear out of them this year. That’s a shame. I love wearing my blazers and feel just as comfortable and casual in them as I do a cardigan. So I’ll definitely be wearing mine to church and such. In fact, I think I wore my black Veronica Beard scuba jacket just a few weeks ago.

Only the 1901 twill blazer on the right is still available.

Honestly, I can tell the fashion industry has taken a major punch in the gut from the COVID-19 pandemic. Most stores are very late getting their fall line out. And all of them are offering fewer pieces than in years past. But most fashion industry major players are admitting that it was past time for a change of pace anyhow. So maybe we’re all going to get off the fast track a little and be more conscientious about our purchases.

But I digress!

What about other completer pieces?

Obviously there are other completers you could consider for your fall wardrobe essentials including moto jackets, utility jackets and puffer vests. But I consider these to be style preferences more than essentials. Remember, wardrobe essentials are…well, essential. But you can certainly make your wardrobe look more like you by adding in a variety of other completer pieces.

Also, I’ll probably do a completer pieces post in a few weeks. Maybe by then there will be more available.

A Versatile Dress

I think every season calls for a versatile, flattering dress. But which dress style you select is a more personal choice. Choose a dress that works for your lifestyle, your style essence and your body shape and proportions.

Sheath Dress

I purchased the Tahari Sheath Dress above in the Nordstrom Anniversary Sale. I think it will work for any season and will be suitable for weddings, funerals, celebration dinners and church. The Sheath Dress is still available, but the price has gone up.


Let’s talk about the shoes that may be essential to your fall wardrobe, depending on your personal style essence, climate and lifestyle.

Booties & Shooties

Booties, and their early fall cousins, shooties or shoe booties, have almost become synonymous with fall footwear. Sure we’ll wear other shoes, but when we really want to achieve that autumn-like style we’ll want to slip into some suede, leather or animal embossed booties.

no longer available

What’s trending in booties:

  • snake embossed
  • croc embossed
  • leopard
  • suede
  • lots of leather
  • pointy toes
  • squared off toes
  • sock booties
  • kitten heels


Of course a gal doesn’t want to wear booties every day, especially as much as we’re staying in. So you’ll probably want a pair of fall and winter flats, too. This year ballet flats are losing favor, but you can certainly still wear them if they’re your jam. Pointy toe flats are in more than ever and, indeed, they do create a more sophisticated look and elongate the leg. But if you can’t wear pointy toe shoes never fear. Square toed shoes are really trending.

suede mules

This year we’re also seeing a lot of animal print and embossed flats, buckles and chains, suede and leather, d’orsays and slight heels. Slides and mules are still in fashion, but loafers are definitely trending, too. In fact, there’s a whole “man shoe” trend riding high right now.


Finally in the shoe department, most of us gals will want to have a pair of sneakers on hand for truly casual looks. You’ll find fashion sneakers ranging from the traditional to wedge heels to platforms. And you’ll also find sneakers in animal print and embossing as well as suede.

I’ll continue wearing these Tory Burch sneakers this fall, along with my more economical Madewell Sidewalk sneakers.

While you can wear most any sneakers during this season, I prefer sneakers that will cover my feet more than some. I also choose leather over canvas during this time of year.

wedge sneakers
I have these wedges from last year and I’m itching to wear them again!

Neutral Handbag

A neutral handbag is an essential in any season, but you’ll probably be ready to change up from whatever you’ve been carrying this spring and summer. If you have invested in a high quality handbag in the past, don’t hesitate to bring it out of its duster bag. But if you’re looking for a new neutral bag, you’ll find plenty in every category.

shoulder bag
I’ll continue to carry my Tory Burch McGraw Leather Hobo this fall and winter.

I suggest looking for a bag in a neutral that works well with your selected wardrobe neutral. So if you wear a lot of black, you may want to go with a black or grey handbag. Or if you wear more browns, you might want a handbag in maple, saddle leather or dark brown.

While you may also want a clutch or small bag in animal print or a trending color, I suggest choosing a neutral colored bag that is big enough for you everyday essentials and one that is easiest and most natural for you to carry.

By the way, you also may enjoy this recent video about Fall Wardrobe Essentials. But this time I’m showing you my personal favorites in each of these categories.

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Blessed for My Day

I love it that Jesus simply laid eyes on Simon and immediately gave him a new name, Peter. He saw the man who stood before Him, but He also knew the man Simon would become. It’s not just that Jesus saw potential in Simon. He saw his destiny.

Simon was probably in his 20s or early 30s when he encountered Jesus. If you had met Jesus face to face when you were in that age range, who would Jesus have encountered? And who is that woman today? How is she different from the woman you were then? Has Jesus changed your name? Maybe from fearful to secure, from arrogant to humble, from flighty to poised, from hot-tempered to composed or from unsure to gracefully confident?

Look, we’ve not been perfected. But surely we’ve been changed by our relationship with Jesus. Don’t be afraid to own the new names that Jesus has given you. Rejoice in the destiny Jesus saw in you and the miraculous way He has brought it forth in your life.

He brought him to Jesus. Jesus looked at him and said, “You are Simon the son of John. You shall be called Cephas” (which means Peter). ~ John 1:42

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xoxo, Kay
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8 thoughts on “Fall 2020 Wardrobe Essentials

  1. YAY!!! So happy to say that I already have all the items you recommend! Thanks for helping us be prepared for fall…whatever that looks like!

  2. Great post, Kay! I am confident that I have the fall wardrobe essentials that fit my lifestyle. While I am so ready for cooler weather, we are still having triple digit heat index’s and the projection is for us to have a warm winter. I will eventually change out my clothes, but it’s way so hot in our attic to start doing that. Great BFMD!

  3. Yep… I have all those taken care of, as well! Thanks for your blog and being a Godly example for so many women. I am 51 and still have 6 kids at home…one has special needs and still in diapers…so add “stay-at-home moms” to the categories of women that read your blog! ?

  4. Thanks Kay. Your post encouraged me to buy a couple of tees and some booties. I need the encouragement for shoe shopping. For me it can be as hard as buying a swim suit. And thanks too for the reminder of a new name from the Name above all Names!