December 11, 2025
Fashion
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Winter Workwear

It’s time again to round up some workwear! This past month I’ve tried to find some workwear outfits that can be mixed and matched for casual or professional looks with perfect for layering. If you are looking for some holiday outfits check outΒ THISΒ post.

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

For reference I’m 5’5, size 12/31, 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.

PANTS

winter workwear, winter office outfits, business casual winter outfits, holiday work outfits, festive workwear, office outfit ideas, workwear inspiration, business professional outfits, women’s workwear over 40, midsize work outfits, winter fashion for work, chic office style, cold weather office outfits, classy work outfits, elevated workwear, corporate style for women, office wardrobe essentials, winter capsule wardrobe, winter outfit guide, what to wear to work in winter, office chic, polished work outfits, stylish office looks, professional winter style, holiday business outfits, office holiday party outfits, winter wardrobe ideas, timeless workwear, comfortable winter work outfits, winter layering for work, elegant business attire

Blouse | Pants | Shoes | Bag
Fit Tips: Blouse tts, L / Pants, tts 12R

Sweater | Pants | Shoes | Bag
Fit Tips: Sweater tts, L / Pants, size up if in-between 12R

winter workwear, winter office outfits, business casual winter outfits, holiday work outfits, festive workwear, office outfit ideas, workwear inspiration, business professional outfits, women’s workwear over 40, midsize work outfits, winter fashion for work, chic office style, cold weather office outfits, classy work outfits, elevated workwear, corporate style for women, office wardrobe essentials, winter capsule wardrobe, winter outfit guide, what to wear to work in winter, office chic, polished work outfits, stylish office looks, professional winter style, holiday business outfits, office holiday party outfits, winter wardrobe ideas, timeless workwear, comfortable winter work outfits, winter layering for work, elegant business attire

Blouse | Pants | Shoes
Fit Tips: Blouse tts, L / Pants, 12R

Blouse | Pants | Shoes | Bag
Fit Tips: Blouse tts, L / Pants, size up if in-between 12R run long

winter workwear, winter office outfits, business casual winter outfits, holiday work outfits, festive workwear, office outfit ideas, workwear inspiration, business professional outfits, women’s workwear over 40, midsize work outfits, winter fashion for work, chic office style, cold weather office outfits, classy work outfits, elevated workwear, corporate style for women, office wardrobe essentials, winter capsule wardrobe, winter outfit guide, what to wear to work in winter, office chic, polished work outfits, stylish office looks, professional winter style, holiday business outfits, office holiday party outfits, winter wardrobe ideas, timeless workwear, comfortable winter work outfits, winter layering for work, elegant business attire

Sweater | Pants | Shoes | Bag
Fit Tips: Sweater tts, L / Pants, 12R

Sweater | Pants | Shoes | Bag | Belt
Fit Tips: Sweater tts, L / Pants, size up if in-between 12R run long

Shirt | Pants | Shoes | Bag | Belt
Fit Tips: Sweater tts, L / Pants, size up if in-between 12R run long

Shirt | Pants | Shoes | Bag | Belt
Fit Tips: blouse tts, L / Pants, tts 12R stretchy in back

Blouse | Jeans | Shoes | Bag | Belt
Fit Tips: blouse tts, L / Jeans, L Petite size up if in-between run small

Sweater | Pants | Shoes | Bag | Belt | Glasses
Fit Tips: Sweater tts, L / Pants, tts 12

winter workwear, winter office outfits, business casual winter outfits, holiday work outfits, festive workwear, office outfit ideas, workwear inspiration, business professional outfits, women’s workwear over 40, midsize work outfits, winter fashion for work, chic office style, cold weather office outfits, classy work outfits, elevated workwear, corporate style for women, office wardrobe essentials, winter capsule wardrobe, winter outfit guide, what to wear to work in winter, office chic, polished work outfits, stylish office looks, professional winter style, holiday business outfits, office holiday party outfits, winter wardrobe ideas, timeless workwear, comfortable winter work outfits, winter layering for work, elegant business attire

Blouse | Jeans | Shoes | Belt | Purse
Fit Tips: Blouse tts, L / Jeans Size up if in between, XL

DRESSES

winter workwear, winter office outfits, business casual winter outfits, holiday work outfits, festive workwear, office outfit ideas, workwear inspiration, business professional outfits, women’s workwear over 40, midsize work outfits, winter fashion for work, chic office style, cold weather office outfits, classy work outfits, elevated workwear, corporate style for women, office wardrobe essentials, winter capsule wardrobe, winter outfit guide, what to wear to work in winter, office chic, polished work outfits, stylish office looks, professional winter style, holiday business outfits, office holiday party outfits, winter wardrobe ideas, timeless workwear, comfortable winter work outfits, winter layering for work, elegant business attire

Dress | Shoes | Purse
Fit Tips: Dress tts, L

winter workwear, winter office outfits, business casual winter outfits, holiday work outfits, festive workwear, office outfit ideas, workwear inspiration, business professional outfits, women’s workwear over 40, midsize work outfits, winter fashion for work, chic office style, cold weather office outfits, classy work outfits, elevated workwear, corporate style for women, office wardrobe essentials, winter capsule wardrobe, winter outfit guide, what to wear to work in winter, office chic, polished work outfits, stylish office looks, professional winter style, holiday business outfits, office holiday party outfits, winter wardrobe ideas, timeless workwear, comfortable winter work outfits, winter layering for work, elegant business attire

Dress | Shoes | Bag
Fit Tips: Dress tts, L

SKIRTS

winter workwear, winter office outfits, business casual winter outfits, holiday work outfits, festive workwear, office outfit ideas, workwear inspiration, business professional outfits, women’s workwear over 40, midsize work outfits, winter fashion for work, chic office style, cold weather office outfits, classy work outfits, elevated workwear, corporate style for women, office wardrobe essentials, winter capsule wardrobe, winter outfit guide, what to wear to work in winter, office chic, polished work outfits, stylish office looks, professional winter style, holiday business outfits, office holiday party outfits, winter wardrobe ideas, timeless workwear, comfortable winter work outfits, winter layering for work, elegant business attire

Sweater | Skirt | Shoes | Purse
Fit Tips: Sweater tts, L/XL / Skirt, XL

winter workwear, winter office outfits, business casual winter outfits, holiday work outfits, festive workwear, office outfit ideas, workwear inspiration, business professional outfits, women’s workwear over 40, midsize work outfits, winter fashion for work, chic office style, cold weather office outfits, classy work outfits, elevated workwear, corporate style for women, office wardrobe essentials, winter capsule wardrobe, winter outfit guide, what to wear to work in winter, office chic, polished work outfits, stylish office looks, professional winter style, holiday business outfits, office holiday party outfits, winter wardrobe ideas, timeless workwear, comfortable winter work outfits, winter layering for work, elegant business attire

Blouse | Skirt | Shoes | Bag
Fit Tips: Blouse tts, L // Skirt size up, XL – wearing shapewear

winter workwear, winter office outfits, business casual winter outfits, holiday work outfits, festive workwear, office outfit ideas, workwear inspiration, business professional outfits, women’s workwear over 40, midsize work outfits, winter fashion for work, chic office style, cold weather office outfits, classy work outfits, elevated workwear, corporate style for women, office wardrobe essentials, winter capsule wardrobe, winter outfit guide, what to wear to work in winter, office chic, polished work outfits, stylish office looks, professional winter style, holiday business outfits, office holiday party outfits, winter wardrobe ideas, timeless workwear, comfortable winter work outfits, winter layering for work, elegant business attire

Cardigan | Skirt | Shoes | Bag
Fit Tips: Cardigan tts, L / Skirt, XL

COATS

winter workwear, winter office outfits, business casual winter outfits, holiday work outfits, festive workwear, office outfit ideas, workwear inspiration, business professional outfits, women’s workwear over 40, midsize work outfits, winter fashion for work, chic office style, cold weather office outfits, classy work outfits, elevated workwear, corporate style for women, office wardrobe essentials, winter capsule wardrobe, winter outfit guide, what to wear to work in winter, office chic, polished work outfits, stylish office looks, professional winter style, holiday business outfits, office holiday party outfits, winter wardrobe ideas, timeless workwear, comfortable winter work outfits, winter layering for work, elegant business attire

Coat | Dress | Shoes | Bag
Fit Tips: Coat tts, LP / Dress tts, L

winter workwear, winter office outfits, business casual winter outfits, holiday work outfits, festive workwear, office outfit ideas, workwear inspiration, business professional outfits, women’s workwear over 40, midsize work outfits, winter fashion for work, chic office style, cold weather office outfits, classy work outfits, elevated workwear, corporate style for women, office wardrobe essentials, winter capsule wardrobe, winter outfit guide, what to wear to work in winter, office chic, polished work outfits, stylish office looks, professional winter style, holiday business outfits, office holiday party outfits, winter wardrobe ideas, timeless workwear, comfortable winter work outfits, winter layering for work, elegant business attire

Coat | Blouse | Pants | Shoes | Bag
Fit Tips: Coat tts, L / Blouse tts, 12 / Pants, 12

Coat | Pants | Shoes | Bag
Fit Tips: Coat tts, L / Pants, 12

Similar Coat | Pants | Shoes | Bag
Fit Tips: Coat tts, 12 / Pants, 12R

Pin for Later | The Recruiter Mom
winter workwear, winter office outfits, business casual winter outfits, holiday work outfits, festive workwear, office outfit ideas, workwear inspiration, business professional outfits, women’s workwear over 40, midsize work outfits, winter fashion for work, chic office style, cold weather office outfits, classy work outfits, elevated workwear, corporate style for women, office wardrobe essentials, winter capsule wardrobe, winter outfit guide, what to wear to work in winter, office chic, polished work outfits, stylish office looks, professional winter style, holiday business outfits, office holiday party outfits, winter wardrobe ideas, timeless workwear, comfortable winter work outfits, winter layering for work, elegant business attire

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