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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

Blazer | Top | Pants | Belt | Shoes | Bag

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

Top | Pants | Shoes | Similar Purse

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

Dress | Shoes | Bag | Bracelet | Bracelet | Watchband

Fit Tips: Dress tts, L

Top | Pants | Shoes | Similiar Purse | Bracelet | Bracelet | Watchband

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

Top | Jeans | Shoes | Bag | Bracelet | Bracelet | Watchband

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

Tee | Pants | Sandals

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

Dress | Sandals

Fit Tips: Dress tts, L

Top | Pants | Shoes

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

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

Top | Pants | Tote | Shoes

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

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

Blazer | Top | Skirt | Shoes | Earrings | Necklace

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

Dress | Sandals | Earrings | Necklace

Fit Tips: Dress tts, L

Top | Pants | Shoes

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

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