20 Transitional Fall Workwear Outfits

It’s that time of year when fall colors are starting to pop up everywhere, but the heat is still kicking! As we move into back-to-school season, I’ve rounded up some workwear outfits that can be worn now and into fall.

If you are new here, I’m a former corporate recruiter who spent over 12 years in business suits. In the past few years, many workplaces have adopted a more casual dress code. I try to mix my love for a classic professional look with a more dressed-down vibe.

Also I LOVE heels, my husband is 6’4 so I’m just used to them. If you need some ideas for flats or more workwear accessories and shoes head HERE.

For reference I’m 5’5, size 12, 38DD. I list the sizes I’m wearing below each image and give my fit tips based on my previous experience with the brand and on the size guides provided.

Top | Skirt | Tote | Shoes

Fit Tips: Top tts, L // skirt size up, XL

workwear outfits, Fall workwear, transitional workwear, business casual, casual outfit, wide leg pant, fall dress, linen pant, midsize outfit, midsize workwear, shirt dress, brown sandals, khaki, utility dress, fall fashion, The Recruiter Mom

Fit Tips: Top tts, L// Pants size up, XL // Blazer tts, L

Top | Pants | Shoes | Similar Purse

Fit Tips: Top tts, L// Pants, 14

Fit Tips: Dress tts, L

Fit Tips: Top tts, L // Pants, size up in a 14

workwear outfits, Fall workwear, transitional workwear, business casual, casual outfit, midsize jeans, wide leg pant, fall dress, linen pant, midsize outfit, midsize workwear, shirt dress, brown sandals, khaki, utility dress, fall fashion, The Recruiter Mom

Fit Tips: Top tts, L // Jeans size down if in-between, 31

Tee | Pants | Sandals

Fit Tips: Tee tts, L // Pants tts, L

workwear outfits, Fall workwear, transitional workwear, business casual, midsize outfit, midsize workwear, shirt dress, brown sandals, khaki, utility dress, fall fashion, The Recruiter Mom

Dress | Sandals

Fit Tips: Dress tts, L

Top | Pants | Shoes

Fit Tips: Blouse tts, L // Pants run tts wearing 14 but they are loose

midsize workwear, teacher outfits, teacher workwear, school outfit, workwear outfits, Fall workwear, transitional workwear, business casual, casual outfit, wide leg pant, fall dress, linen pant, midsize outfit, midsize workwear, shirt dress, brown sandals, khaki, utility dress, fall fashion, The Recruiter Mom

Sweater | Skirt | Shoes

Fit Tips: Sweater runs large, wearing L // Skirt tts, L

Blazer | Top | Pants

Fit Tips: Blazer tts, L // Blouse tts, L // Pants L regular

Blazer | Top | Pants | Shoes

Fit Tips: Blazer tts, L // Blouse tts, L // Pants XL regular

Dress | Shoes | Blazer | Similar tote

Fit Tips: Blazer tts, L // Dress tts, L

Top | Pants | Tote | Shoes | Belt

Fit Tips: Top, L // Pants size up, XL

workwear outfits, teacher outfit, teacher style, Fall workwear, transitional workwear, business casual, casual outfit, wide leg pant, travel pant, curvy pant, midsize pant, midsize outfit, midsize workwear, shirt dress, blazer, pumps, herringbone, plaid, lace top, wide leg pant, khaki pant, belt, wide leg pants, utility dress, fall fashion, The Recruiter Mom

Top | Pants | Tote | Shoes

Fit Tips: Top, L // Pants tts, L

workwear outfits, teacher outfit, teacher workwear, Fall workwear, transitional workwear, business casual, casual outfit, teacher outfit, wide leg pant, travel pant, curvy pant, midsize pant, midsize outfit, midsize workwear, shirt dress, blazer, pumps, herringbone, plaid, lace top, wide leg pant, khaki pant, belt, wide leg pants, utility dress, fall fashion, The Recruiter Mom

Blazer | Top | Pants | Tote | Shoes

Fit Tips: Blazer size up for linen wearing L // Top, XL // Pants tts, L

Dress | Shoes | Blazer | Belt

Fit Tips: Blazer tts, L // Dress tts, L

fall workwear, teacher outfit, teacher workwear, business casual, wide leg pant, midsize workwear, fall outfit, floral top, black pleated skirt, green dress, shirt dress, brown blazer, herringbone jacket, pointed toe, flats, chocolate brown outfit, nordstrom fashion, teacher outfit, teacher workwear, TheRecruiterMom

Fit Tips: Blazer tts, // Blouse tts, L // Skirt size up, wearing a L, but need XL

fall workwear, business casual, wide leg pant, midsize workwear, fall outfit, floral top, black pants, nordstrom fashion, teacher outfit, teacher workwear, TheRecruiterMom

Dress | Sandals | Earrings | Necklace

Fit Tips: Dress tts, L

Top | Pants | Shoes

Fit Tips: Blouse tts, 12 // Pants tts, 12

The Recruiter Mom is participant in the Amazon Services LLC Influencer/Associates Program, an influencer/affiliate advertising program designed to provide means for sites to earn advertising fees by advertising and linking to https://www.amazon.com/shop/ryannejanca

The Recruiter Mom LLC uses affilate links on this page. Purchasing an item through a link may result in a commission. Merely clicking on a link does not result in a commission, but if a qualifying purchase is made, a comission is earned.

Read more about my site, privacy, and disclosure policies here.