Dressy-Casual Fall Essentials for the Work-at-Home Mom

by - October 22, 2020

Working at home comes with its own set of rules about how to dress. For the most part, unless you have a meeting, be it face-to-face or via Zoom, you don't have to worry about what you look like. That said, I am a firm believer in dressing for success always. When I get up and get dressed, no matter what I decide to put on, I have a more productive day.

My typical daily style could be described as dressy-casual. I don't wear traditional heels much anymore, but most days I do prefer a little added height. Slacks really don't have a place in my closet anymore either, although I do still have them for special occasions. I tend to stick with jeans or twill pants, or on days where I'm feeling a comfier vibe I'll pull out a pair of joggers. I like to dress comfortably stylish, and nearly all of my outfits feature some type of print.

Now that our weather pattern is starting to show more signs of Fall, I've started drifting into that portion of my closet. We've only had a few days that were cool enough for a sweater or sweatshirt so far, but I have been getting to use some of my favorite layering pieces. Fall (which is pretty much what our winter amounts to compared to other parts of the country) is truly my favorite season to dress in, and today I wanted share my essentials for the season.

Sizing note: I'm 5'2" and wear size 6/8 or medium in tops and dresses, size 6 in pants and skirts, and size 7 in shoes.

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boyfriend jeans leather pants

Not-So Basic Bottoms

I feel like skinny jeans are probably here to stay, especially during boot season, but I'm kind of over them, ya know? These days I find myself reaching for looser denim styles, like my fave boyfriend jeans from Old Navy, button-fly jeans, or even bootcut ones. For one thing, super skinny jeans aren't exactly the most comfortable jeans in the pile, are they? They definitely have a place in my closet, but I love that little bit of personality these other styles add to my outfit.

For something a little edgier, why not reach for some leather? I'm not much of a leggings girl, myself. That said, I bought a pair of faux leather leggings several years ago off a $5 rack to try and loved them. I wore them out, literally, and hadn't found a replacement pair at a price point I was comfortable with for a couple years. This year, though, I decided to invest in a pair of faux leather pants - you know, a pair with a button and zipper - and got this pair on sale from Express. I had to size up to a 10 because they run super small, so they're a smidge longer than I wanted but I feel like they're probably going to draw up a little bit.

color block sweater purple sweatshirt

Warm Tops

It goes without saying that comfy sweatshirts and cozy sweaters are Fall wardrobe essentials. I've really embraced sweatshirts this year. I'm not sure why I didn't own any before, to be honest, but I've added four to my closet so far. I love the casual vibe a sweatshirt gives off, and with the right cut, color and/or print, you can definitely pull off a look that's more athleisure than sloppy.

Considering how short our cold season is, it's kind of crazy how many sweaters I own, but in my defense I literally keep sweaters for years and years. I actually only recently started updating my sweater collection. Some of my basic, classic styles had finally reached the end of their days and needed replacing, and I wanted to add a few trendier ones like the color block one in the pic above and this pretty lantern sleeve one that I can't wait to wear.

long cardigan chunky cardigandenim jacket white leather jacket 

Don't Forget Your Layers

Layers are an essential part of southern Fall outfits. Our fall (and even winter) consists of cooler mornings and evenings and midday temps that are sometimes in the mid-80s. Having removable layers is a must if you want to survive the still running air conditioner inside but don't want to suffer a heat stroke outside.

So let's start with your main ingredient: the top. My fall layering essentials consist of t-shirts, henleys, and tanks. Stripes are a classic layering item, and even though it feels like you see them on literally everyone these days, you need at least one striped t-shirt in your closet (I have at least five just in black and white). For skirts, I recommend this pretty button-front camisole from Amazon. I have it in the white and cream color, and wear them constantly.

Now to top it all off, add a jackets or cardigan. I rotate between my denim, suede, and leather jackets pretty much all year long, but I also have some basic and patterned blazers to rotate into the mix, and I'm really digging this fitted tweed jacket. If you want something a little cozier, opt for a cardigan. I'm a fan of the long duster-style knitted cardigans like this one (mine in the pic is old), and this chunky burgundy one is ridiculously soft.

 leopard print sweatshirtstriped dress

Pop in a Pretty Print

When most people think of Fall prints, their mind's eye immediately pictures plaids. While I love a good plaid just as much as the next person, it is not the end-all be-all print of the season.

Leopard print has pretty much cemented itself as a year-round basic, but the season it lends itself most fluidly to, in my opinion at least, is the fall. You can go big and bold, like my sweatshirt above, or just throw in touches here and there with a belt or simple sneakers.

I've already said it once in this post: Stripes are another year-round staple you need to have in your closet. But who said anything about sticking with a basic black-and-white striped shirt? Mix things up with striped dresses, shirts, and skirts in bold fall colors. Take my dress pictured up above. The olive green and deep red mixed with the rougher texture of the fabric make this dress feel more like fall than spring.

I adore florals for fall (well, any season really). The easiest way to making them work in cooler months is to darken them up. You can do this by buying floral prints set on a dark background (like my purple floral dress, seen below) or layering them with traditional fall colors (like how I topped my ruffled skirt with an olive tee, also below).

rust floral skirt purple floral dress

Walk It Out

No outfit is complete without shoes. My ankle boots come out as soon as the calendar strikes September, even if that's still technically part of southern summer. I tend to wear ankle boots way more often than tall boots, mostly because it's rarely cold enough for their bulkier companions. As a result, I have about triple the amount of ankle boots to choose from as tall boots (of which I literally only have six pair compared to at least 20 booties).

This year I've really embraced sneakers. The beige pair in the photo above have become my neutral go-to now that the weather has cooled down some. I originally bought them for summer but they mesh with my fall clothes better. I also have a pair of leopard print, faded navy blue Converse, and black skate shoes.


I'm not big on accessories. I tend to wear the same jewelry all the time and it's almost always too hot for a scarf. But I wanted to include this category because I've fallen in love with knotted headbands and ponytail scarves. I'm pretty unaccomplished when it comes to fixing my hair, other than letting it do its own thing or using a straightener, but these are pretty solutions that don't require a lot of effort.

What are some of your favorite go-to fall clothes and/or shoes?

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