Fall Work Wear Inspiration

I’ve been getting a bunch of requests for fall work wear, but let’s face it — it’s just not my wheelhouse. Then I started thinking, a bunch of ladies in my JLS Tribe rock the work wear looks, so I asked if anyone would be willing to submit some looks to be featured on the blog, and lo and behold, the submissions started coming in!

So over the past few weeks, I’ve been collecting fall work wear looks from real women and regular readers of my blog, and today I’m sharing them with you! I hope this provides you with some good fall work wear inspiration.

A lot of these looks lean towards summery because so many of us have had warm weather this fall, so if you like this post, I can do it again when it gets colder.

Let’s get started! (And if you like this post, I’d love for you to pin the image below so others can find it!)

2019 Fall Work Wear Inspiration: 21 Fall Work Wear Outfits for your style inspiration!

Fall Work Wear Inspiration

Heather is a teacher in southern California, and she’s 5’9″. In her words, “I’m a 4th grade teacher and comfort is important.”

Here are a few of the outfits she’s been wearing to work lately. I did my best to link exact items or something similar, but in some cases I just left the description she gave me.

LOFT sleeveless floral top // similar LOFT pants // short-sleeved cardigan (Old Navy) // sandals (Vince Camuto) // Madewell tote

blouse (Böhme) // Mother Looker ankle jeans // Sam Edelman GiGi sandals // black blazer (Nordstrom)

printed cami (LOFT) // white cardigan (LOFT) // navy wide leg linen pants (Caslon) // Tory Burch Miller sandals

“Choose Kindness” tee (Amazon) // AG straight ankle jeans // Superga sneakers // gold and stone drop earrings (Anthropologie)

Karen is local to me, and I actually met her a few weeks ago at the Kendra Scott bar party! She sent me several of her recent outfits as well. Karen is 5′, so she wears petite sizes, and she describes her workplace as a casual office.

Nic + Zoe cardigan // black tank // similar khaki pants // similar nude patent pumps

And this is another variation on that outfit — she swapped out the necklace and the shoes. She said she is welcome to constructive feedback and feels she struggles with proper proportion and fit, but I think she looks very balanced in these looks!

Nic + Zoe cardigan // black tanks // similar khaki pants // similar black pumps

cardigan (Charter Club) // forest green sleeveless moc turtleneck (Topshop) // similar khaki pants // similar snake print pumps

Here’s what Karen said about these next two looks: “I wore the nude Clark sandals but really wanted to wear the grey booties. I wasn’t sure if they looked okay. I am also concerned about trying to look too young… I don’t want to look silly.”

I told her the grey booties look great and make the dress look more modern, although I like it with the nude wedge sandals too. I think they’re more summery, and the booties bring it into fall. What do you think?

similar denim jacket // stripe knit dress (purchased at local craft fair) // Clarks sandals // similar open toe booties

And here’s a couple more she sent me, one with the cardigan and one without:

similar blouse // cardigan (Caslon) // navy pants (Banana Republic) // similar nude patent pumps

Kristie lives in Connecticut, and she also wears petite sizes.

gray boyfriend jacket // orange top (LOFT) // navy pants (LOFT) // Sam Edelman Felicia Flats // earrings (Nickel + Suede)


similar cardigan // floral top (LOFT) // grey pants (LOFT) // Sam Edelman Florence ballet flats / Nickel & Suede gold leaf earrings (size small) // similar necklace

Love the pop of pink in her shoes with this next look!

stripe top (LOFT) // black pants (LOFT) // Sam Edelman Berry Suede Felicia flats

Sheila is a teacher in the Seattle area, and she’s 5’3″. She says: “I wear a badge on a lanyard and a microphone at work, so necklaces aren’t a choice for me.”

This first look was a fan gear day.

mustard blouse (Walmart) // navy blue skinny pants (Madewell) // scarf (Madewell) // Sam Edelman Rosalie leopard flats

Today was about comfort, she says… she looks awfully good for comfort!

similar Halogen floral blouse (Halogen) // stretchy black pants // Naturalizer Hydie wedges

similar cognac leather jacket // olive green top // black pants // snake print loafers (Marc Fisher)

And this look is probably my favorite of hers. Such a great combination of colors.


stripe top (Walmart) // mustard blazer (thrifted) // charcoal skirt (thrifted) // plum wedges (Impo) //

Laura is 5’7″ and typically wears size 6 or 8. She reports all these items run TTS. I’m loving the leopard shoes with green top — such a striking contrast.

Here’s what she says about these pants: “The best part of these pants is the slash pocket. Hip/Side Slit pockets tend to flare out on me due to my pear shape & hips. That flare only adds to a part of my body that I’m trying to minimize.”

Ann Taylor Essential Shirt (size small) // LOFT Skinny Ankle Pants in Curvy Fit (size 6) // J.Crew Factory Zoe calf hair d’Orsay flats // belt (Ann Taylor) // necklace (Nadri)

Fonda is required to wear professional attire when she is in the office and in court, and in addition to working full-time, she blogs at Southern Savvy Chic.

Here’s what she says about her style: “As an over 40  fashion blogger, I’m here to provide ideas and inspiration for fashionable work/office outfits and casual outfits for ladies of all ages. I’m a petite pear shape who doesn’t always follow the rules.”

J.Crew Factory schoolboy blazer // blouse (Ann Taylor) // leopard skirt (J.Crew Factory) // similar black pumps

blazer (LOFT) // pants (LOFT) // blouse (Amazon) // leopard pumps (DSW)

J.Crew Factory schoolboy blazer // blouse (Nordstrom) // red pants (Worthington) // shoes (Payless) // (Kendra Scott)

grey blazer (J.Crew Factory) // floral blouse (JCPenney) // pants (LOFT) // shoes (Payless) // snake print purse (Nine West/Belk)

And finally, I’ll share one of my own that I’m pretty proud of. If you’re a regular, you may have seen this before, but I needed a picture for my featured image up top, and I felt weird using one of these lovely ladies for that!

If I don’t include the details here, someone will surely ask. Also, when I posted this look originally, my exact skirt wasn’t online in the black, but now it is!

All of these pieces run true to size; I’m wearing a small in the blouse, skirt, and jacket. Oh, but I sized up half for the shoes.

stripe blouse // black pencil skirt // croc print mules // cognac leather jacket // similar tote // earrings

I hope this post was helpful for those of you looking for work wear! If you like it, let me know, and I’ll try to do another one in a few weeks!

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