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Fall 2019 Wardrobe Essentials

August 30, 2019

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 2019 Wardrobe Essentials day!

Today’s post is part of this year’s style series, Building a Wardrobe that Works for You. If you’re new to the series, you might want to catch up by at least reading the first post in this 2019 series, 9 Keys to Building a Wardrobe that Works for You. According to that post, one of the keys is having the Essentials. These somewhat “boring” 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!). 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.

New AG Mari Straight Leg Jeans with High Waist in 12yr Persistent

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.

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.

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.

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).

I own the black pants in the photo above. They are a little pricey, but I’ll be wearing them for years. 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.



You’ll find t-shirts in all of my wardrobe essentials lists. In fact, I think I need to do a 5th wardrobe essentials list once I’ve completed my winter list. The 5th list would be the year-round essentials. Anyhow, t-shirts are year-round essentials in my book.

Long Sleeve 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. But it’s also great to have a few stripes or other colors.

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 and crew neck tees serve their purpose, too.

Chambray Shirt

I have a feeling chambray shirts will 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.

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.

Other Layering Base Pieces

This is one of those categories where your personal style essence really determines the direction you take. The bottom line is that during fall we tend to want to layer on our clothing so we can also take layers off as we heat up. And that’s a beautiful way to dress!

But for every trending or classic outer layer you buy, I suggest you have at least two to four different base layers you can mix with it. So besides the t-shirts I mentioned above, you may want to incorporate into your fall wardrobe essentials list one or more of the following:

  • lightweight turtlenecks
  • camisoles
  • tanks
  • long-sleeve button up shirts
  • silk blouses

For instance, if you have a denim jacket (and I hope you do!), you can create completely different and lovely looks when you layer that jacket over a) a silky, print camisole b) a colorful long-sleeve button up shirt or c) a silky leopard print blouse. Personally I’m making sure my fall closet is stocked with a couple of each of these in versatile prints and colors.

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 definitely trending. That’s great news for tall gals like myself. But there are plenty of other styles in the offerings, so you’re sure to find something that suits your taste, body shape and proportions.

When selecting cardigans I’d use the “invest in classics/save on trends” philosophy. I splurged on a couple of cashmere blend long cardigans in the Nordstrom Anniversary Sale (sold out but these are similar), but I got them in neutrals that I can wear for years. But if you want to buy something in the trending teals, berries, pistachio greens or golden yellows, I’d spend less on bargain finds.

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 decent, fitted blue denim jacket. But after that, the sky’s the limit! In fact, I recently picked up this snakeskin denim jacket and can’t wait to wear it.

snake around jacket (the small fits me nicely)


Y’all, blazers are trending big time this fall. So they’re not just for the ultra classic dresser or the working gal. More than ever, a pretty, well-fitted blazer is a fall wardrobe essential. And they’re so very versatile.

I have this black one (and love it), but I just recently ordered this houndstooth girlfriend blazer from Gap. Maybe you’ll see it in an upcoming blog post if it fits well. Of course, plaid is definitely hot this fall and winter. So if you already own a solid one – or you just prefer plaid! – consider one of these in colors that suit you best.

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.

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.

But here are a few things to consider when selecting that one dress for the fall:

  • the midi length (just below the knee) is trending and looks great on most of us older gals.
  • wrap or faux wrap dresses are almost universally flattering and easy to wear.
  • dark florals are trending but be careful to select modern looking florals and resist those reminiscent of the Little House on the Prairie.
  • choose a dress that works well for your lifestyle and the events you have coming up this fall and winter.


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.

What’s trending in booties:

  • snake embossed
  • croc embossed
  • leopard
  • suede
  • lots of leather
  • pointy toes
  • western embellishments and style


Right now we might can imagine slipping on some booties, but knee-high boots just sound hot, hot, hot. I get it. But deeper into fall I know I’ll be anxious to put on some skinny jeans or cords and zip up my boots. You will, too!

This year knee high boots seem to be taking the spotlight and over the knee boots are less prevalent on the scene. If you own over the knee boots, you can certainly still wear them. Shoot, if you just love them you can still buy them and wear them. But I, personally, am kinda glad they’re not the rage this year. I never really got them.

Conversely, riding boots seem to be returning to fashion. Not that you ever couldn’t wear them. But they’re more on point this year. You’ll also see even more suede and quilting, as in the photo above.


Of course a gal doesn’t want to wear boots or booties every day. 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.

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.

Do you need to add a pair of sneakers to your fall wardrobe essentials?

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.

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.

Season Accessories

In the fall our accessories tend to change from the warmer months, too. This is when I like to once again start wearing both neck scarves and longer scarves. And of course, right now we’re seeing more outfits belted, too, so I suggest having both a couple of neutral belts and maybe a leopard or snake print belt. As far as jewelry, you’ll definitely want some basic gold and/or silver pieces to mindlessly reach for to top off your outfits.

Also hats are definitely trending. I picked up a lovely fedora in the Nordstrom Anniversary Sale that I’m looking forward to wearing. What accessories do you need to add to your fall wardrobe essentials?

Well that’s a wrap! Remember, if you’ve missed any of the Building a Wardrobe that Works for You series, you can check out the previous posts here. You’ll also find access to the series under the “fashion” tab at the top of the website.

If You’re Visiting from Pinterest…

I hope you’ll take a few moments to look around Dressed for My Day. You might want to…

  • find out more about me here.
  • check out my other fashion posts here.
  • discover the answers to my frequently asked questions here.
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Blessed for My Day

The Bible tells us that the Lord inhabits the praises of His people. In other words, His presence dwells in the midst of praise and trust in Him. Recently I heard one preacher say that praising God provides a landing pad for His fullness.

When you feel alone in your struggles or concern, check whether or not you have put down a landing pad for God. Have you spoken more complaints and concerns and doubts? Or have you filled your space – your office, your car, your home, your walking trail – with praises for God? Today choose to praise Him first, and then share with Him your cares.

I will sing to the Lord as long as I live;
    I will sing praise to my God while I have being.
May my meditation be pleasing to him,
    for I rejoice in the Lord. ~ Psalm 104:33-34

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xoxo, Kay
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9 thoughts on “Fall 2019 Wardrobe Essentials

  1. Hello Kay,

    I really love your posts! I look forward to seeing them in my email every day. I have a quick question regarding sizing for the snake print jean jacket. I’d like to order it and I usually wear a small or medium size, depending on the item. But it says to size down, I’m not sure if I should go with the extra small or small. What size did you order since we’re similar in size?

    Thank you!

    1. Hi Donna. I have a small in the snake print jacket and, like you, usually wear either a medium or small. So I’m suggesting a small. I hope that works for you. It is a fitted jacket, but doesn’t feel tight on me at all. But I certainly wouldn’t go with an x-small for me. And it’s definitely a keeper!

  2. Good morning Kay. Great post today. It’s cool here in the mornings, you can feel fall in the air! I am wearing a duster today that I’ve had for a couple of years. I’m sure by afternoon it will be off but for now it’s keeping me nice and warm and stylin’?

  3. Hi Kay! Thank you for putting this post together. I am going to use your shopping widgets to find a chambray shirt. It was 55 when I got up this morning, which was so refreshing. We can’t wait for fall weather to get here. I hope you are having a great day!

  4. Hi Kay, this post was wonderful! I’ve been reading your blog since it started and love how thorough and how much content is in each post. I love fall fashion, especially here in the Cincinnati area (I’ve lived here for 15 years, also a southern transplant). We have several months of cozy clothes and boots!

    1. Well thanks so much for letting me know, Beth. I’m really glad you’re enjoying the blog. I appreciate you reading! Here’s to a great fall!

  5. This is such an excellent post, Kay, thank you! I am saving it for future reference. I can’t imagine how much time it must have taken to put this together! Blessings!