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Fall 2021 Wardrobe Essentials

August 24, 2021

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 2021 Wardrobe Essentials day!

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 ladies 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!).

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.

I’ve also decided that this past year has made a significant and lasting impact on how we dress. Our styles changed even more than fashion trend reports had initially predicted, due to stay at home orders, less socializing, more working from home, the desire for comfort and more time being spent outside. So I’ve added a few items to our wardrobe essentials list for the very first time this year. See if you can spot those making a premiere appearance.

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 woman who dresses more professionally most days, you’ll want some great looking denim to wear for more casual occasions.

Relaxed Everyday Jeans from Talbots
I ended up going down a size from these that I’m showing here. I’m wearing an 8 here, but I purchased the 6s later in these Talbots Relaxed Everyday 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.

Straight Leg Jeans with Sport Sandals
Frame Le Sylvie Straight Leg Crop Jeans with Raw Edge

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.

Comfort Sandals and Jeans
Kut from the Kloth Elizabeth Fab Ab 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.

White Tee with Jeans and a Blazer
Balloon jeans continue to trend this year, but there are plenty of other slimmer silhouettes if you don’t prefer this style.

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 Neutrals

While I tend to wear jeans most fall 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).

Accessorize to Maximize
See the original post from last year for details.

My primary neutral in my closet is black. I also wear brown, some camel and grey in the fall and winter. But for me a pair of black slacks is a must. But you could absolutely opt for grey, navy, olive green, camel, etc. I like for these pants to be good quality, have a classic silhouette, be constructed in a versatile fabric that keeps its color and shape and be a versatile length.

I’ve mostly included pants that I’ve tried and liked in the shopping widget below. I also have these Talbots Hampshire Ankle Pants in fawn and black. They’re great pants. Oh, I actually have them in the curvy fit.



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

Button Up V-Neck Cardigan
See the original post // v-neck white 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.

Pomegranate Red Pants
See the original post from last year. // 3/4 length sleeve t-shirt in lots of colors

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 as well as the henley collar is very on trend and would reflect a romantic personal style aesthetic among others.

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.

Styling a Column of Denim
See the original post for details. // Similar chambray or 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.

Talbots Classics
See the original post for details. // Similar chambray or denim shirt

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.

Style Formula #1 - Top This!
See the original post for details.// blouse no longer available

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 available. But cropped styles are trending high. And I think the mid length that hits just below the hip has made a resurgence to the top of the list.

Trending this Fall
See the original post for details. // Cardigan (purchased in the Nordstrom Anniversary Sale)

Perhaps the most popular silhouette this fall is the v-neck, boxy, slightly cropped button up sweater, like the one I’m wearing above. And cable knit is also promising to be the most trendy texture.

Button-Up Cardigan
See the original post for details. // 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.

Rise & Shine
See the original post for details. // Levi’s denim jacket

This year I’m especially seeing a lot of boxy, field coat or chore jacket styles in denim. But I’m also seeing denim blazers and other more fitted silhouettes. So simply choose the one that fills a hole in your wardrobe, that works for your body shape and proportions and that you love. This year I’ll still be wearing my Levi’s denim jacket, undoubtedly. But I also purchased this fitted tailored denim jacket.


Blazers were set to trend high again last year. But since many of us got out a good bit less, we didn’t wear them as much last fall. So maybe we’ll get to make up for that this year. 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’ve really enjoyed wearing my linen blazer this summer, so I know I’ll be grabbing my more fallish ones soon.

Butterfly T-Shirt with Romans 12:2
See the original post for details // fatigue blazer (almost sold out)

We’re seeing almost every silhouette imaginable in blazers this year. So choose the one that works best for your body type. I love a long blazer for a slenderizing and casual effect, but if you prefer something more fitted or shorter, you’ll find plenty to choose from. In this post I showed how you can actually wear a polished suit jacket casually with jeans.

Suit Blazer
Italian Luxe Knit Blazer (25% off) // See the original post for details.

But if you don’t think you’ll wear a jacket as part of a suit, I’d probably opt for a more casual blazer. I love this casual washed blazer from Talbots. It’s a nice weight for fall and I’ll probably pull it out again in the spring. It’s also available in navy. And it’s 25% off right now.

Transition to Fall OUtfit
Casual Washed Blazer (also in navy, 25% off) // See the original post for details.

What about plaid blazers? Are they still fashionable? Absolutely. They may not be quite as versatile, but I love having a plaid blazer in my wardrobe for fall.

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 have a video in the can for next Wednesday, September 1, with five essential completer pieces. 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.

Tahari and Eliza J Dresses
Tahari Asymmetrical Knot Sheath Dress // Eliza J Flutter Sleeve Belted Crepe Dress // Karl Lagerfeld Royal Pump // Halogen Teardrop Earrings  // Coach Turnlock Clasp Satchel

I purchased the above dresses in the Nordstrom Anniversary Sale, but they’re still available. The Tahari Asymmetrical Knot Sheath Dress has a classic silhouette and comes in a beautiful red and black, too. The Eliza J Flutter Sleeve Belted Crepe Dress has a more modern vibe so you might not wear it as many years, but it is a classic color.


Let’s talk about the shoes that may be essential to your fall wardrobe, depending on your personal style essence, climate and lifestyle. Here’s a bird’s eye view of the fall 2021 wardrobe essentials in the shoe category.

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.

See the original post for details.// Eileen Fisher Joss Knit booties

But the booties I’m wearing above are actually knit. So I think they’re going to be a great choice for early fall. Look for booties that fit your lifestyle, but also your pants. That’s right, you’ll want booties that will work optimally with the pant styles you choose to wear. That’s why this year Chelsea boots and other silhouettes with narrow shafts are really trending.

It’s small, but I created the following graphic for this past Saturday’s subscriber newsletter where I answer reader questions each week. (If you’re not subscribed to my weekly newsletter, you can fix that right here!)


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, too.

Houndstooth Pants
Similar Mules // See original post from last year for details.

This year we’re still 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. Another trend I’m noticing is gun metal leather and faux leather shoes. I ordered these gun metal loafers from Talbots yesterday and can’t wait to get them. They’ll look so sporty and elevated with black or blue denim.

I also wanted to let you know that I recently became a brand ambassador with Sarah Flint shoes. These exquisitely handcrafted, Italian leather shoes are on par with other luxury brand shoes made in Italy, but are sold only directly to consumer. So, while still an investment, Sarah Flint footwear costs considerably less than their peers. Plus, if you shop with my discount code – SARAHFLINT-BAKAYH – you can get $50 off your first purchase of Sarah Flint shoes.

Sachetto Ballet flats // Natalie

I was gifted the Sachetto Ballet flats (I chose the black Nappa) and I love them. But after feeling how amazingly comfortable they are, I turned right around and purchased the pointy toe ballet flat, the Natalie. I think with these two pairs of versatile and all-day-comfortable flats, I’ll be set for the fall and winter.

I know the Sarah Flint shoes will not be for everyone. And I’ve even found comparable “looking” shoes for you in the shopping widget below. But if you are someone who especially needs or loves extremely comfortable shoes, I think these are worth the investment.


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 platforms. And you’ll also find sneakers in animal print and embossing as well as suede.

Jazzed Sneakers
See the original post for details. // P448 Thea Platform Sneakers

I’m also continuing to see the chunkier, more retro trainers. They’re a fun choice if you’re looking for a second pair. But I think it’s smart for most of us to have a pair of classic white leather sneakers in our closets, too.

Barrel Pants with Retro Trainers
See the original post from this spring for details. //

Neutral Handbag

Let’s round up this fall 2021 wardrobe essentials list with a 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
Social Threads Faux Leather Messenger Bag

Whether you prefer genuine leather or suede or you’d rather carry faux or vegan leather, you’ll find a selection of bags in the colors that work best with your wardrobe. This year backpacks continue to trend. But we’re also seeing lots of shoulder bags in new silhouettes as well as more traditional satchels.

Coach Handbag
Coach Satchel (purchased in the #NSale, but still available)

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.

I’ll be sharing more wardrobe pieces for fall in the coming days. I’ll do a deep dive into fall boots for sure. And I have that video coming with 5 completer pieces for fall. Are there other fall 2021 wardrobe essentials you’d like for me to do a designated post on? Let me know!

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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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20 thoughts on “Fall 2021 Wardrobe Essentials

  1. Happy Birthday to James! What an informative post! While I don’t like changing out my closet, I am looking forward to getting out my handbags and shoes, in particular. It’s going to have to cool down here before I venture up in the attic though. Our lows are still in the 70’s. As a GA native, you know what it’s like. Have a great day!

  2. Great post! Very inspirational!! Love the chambray shirt and dark taupe combo. Very striking. Thanks for the info and inspiration at the end of your posts. Always look forward to reading. ❤️

  3. A wonderful “Blessed for my day” devotional today. So true how God can change our life when we focus on Him.

  4. What a great post! It’s really got me thinking about what to wear as the weather transitions and the timing is perfect as I’m about to reorganize my closets. Congratulations on the new affiliation with Sarah Flint! I tried to click on the Sarah Flint shoes but kept getting error codes. Oh dear! Your scripture post really hit home with me today and made me ask myself if I’m reflecting who God has turned me into over the decades or if I keep seeing the old me. Ooof.

    1. Hi Martha. Thanks so much for reading and sharing your thoughts. I’m so sorry about the Sarah Flint links and thanks for alerting me that they were malfunctioning. I’ve corrected them now. Have a great day!

  5. Great post! I am currently beginning to switch out my closet, so this post was very timely. Unfortunately, I need a wide shoe and most are medium only. Also, due to heart surgery, I need to cover my décolletage, so V-neck and scoop necklines are not flattering.

    1. Hi, MJ. Kay also has a discount code for Calla shoes. Although they were designed for people with bunions, they are also great for those of us who just have wider feet. I have a pair of their gray flats that I just love – high quality leather, good arch support, and (yay!) enough room in the toe box. You might want to check them out.

  6. Loved this post! I noticed the navy top and burgandy pants and had never thought to put them together! I love navy and now there is another combination to try. I also think you look fabulous in the rusty brown sweater and black slacks. I buy browns but make the error of only wearing them with nuetral beiges and other browns. I know I need color to feel comfortable with nuetrals and brown, thanks for showing me the way…

  7. Great post, Kay! I’m in the market for a couple of blazers. I’m thinking black and camel.
    Happy birthday to James!

  8. Happy Birthday James.
    What a lovely post. Your ideas have helped me so much plan/update my wardrobe to dress beautifully.
    And I always pull a gem out of your devotions.
    Be Blessed.

  9. Hi Kay,
    I love the Eliza J dress & clicked in it. Several reviews said it ran 1, even 2, sizes small. Did you find that to be the case or did you go with your usual size 8?
    I follow you faithfully, appreciate your work very much, & always love your BFMD touch at the end!

    1. I’m wearing my usual size 8 in the photo. But I didn’t keep the dress. I would have sized up to a 10 if I did. Lovely dress, just didn’t need it.

  10. I tried on my favorite brown boots from a couple of years ago and they have shrunk. I think my feet have flattened out due to wearing only flats, flip flops and house shoes for two years. I have bigger feet! So I’m looking for a new pair of brown boots this year. Thank you Covid.

  11. Thank you, Kay, this was an incredible post with so many helpful tips. Thank you for the time you take to help others
    look and feel their best. I bought my first camel blazer on sale last winter after seeing you in yours and can’t wait to wear it as the weather gets cooler here. Loved your blessed comments today and my journey with Jesus has changed my name into gracefully confident. So thankful!!

  12. I love this post! Thank you for sharing. I’m so ready to wear Fall colors and styles. I have quite a few pieces that you mentioned, and a few that I’d like to get. I’m now excited to put together some outfits. Your wardrobe is is beautiful. Happy Birthday to James.

  13. A little slow reading this post this week, but WOW! Great post full of all the info and items we need for fall and most likely winter for us Texans!! Thanks for keeping us on track with these great shops lists!! Have a blessed day!

  14. Love this post, it’s more me since I’m retired!
    Look forward to reading your post each day especially the devotional!