Classic Outfits for Work & Weekend

As I’m about to turn 46 I started thinking about my personal style. After 15 years in a professional work environment I’ve always leaned more classic, conservative when it comes to dressing. Although I realized in the past few years I’ve been swayed by trends or things I’ve seen on friends (of different ages and body types). After a huge closet clean out I decided that this year I’m leaning into outfits that are classic, comfortable and less what’s “trendy”. One of the easiest ways I’ve found is sticking to staple pieces in neutral colors.

I’ve been looking through my closet and pulling out all the items that really fit well, feel amazing and can be worn a ton of ways. I’m still narrowing down to my absolute favorites in each category but here are some recent outfits I’ve been loving.

Winter Workwear, Workwear Over 40, Business Casual, Workwear Jeans, Winter Coat, Workwear Jacket, Lady Cardigan, Wide Leg Jeans, Wide Jeg Pants, Pleated Pants, Spring Bag, Winter Bag, Workwear Shoes, Winter Outfit, Midsize Outfit, Quince, AYR, Ann Taylor, Amazon, Loft, Casual Workwear, Over 40 Fashion, Midsize Fashion

For reference I’m 5’5, size 12/31, 38D. 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.


Winter Workwear, Workwear Over 40, Business Casual, Workwear Jeans, Winter Coat, Workwear Jacket, Lady Cardigan, Wide Leg Jeans, Wide Jeg Pants, Pleated Pants, Spring Bag, Winter Bag, Workwear Shoes, Winter Outfit, Midsize Outfit, Quince, AYR, Ann Taylor, Amazon, Loft, Casual Workwear, Over 40 Fashion, Midsize Fashion

Top | Sweater | Jeans | Sneakers | Bag

Fit Tips: Sweater tts, L // AYR Jeans size up, 32

Winter Workwear, Workwear Over 40, Business Casual, Workwear Jeans, Winter Coat, Workwear Jacket, Lady Cardigan, Wide Leg Jeans, Wide Jeg Pants, Pleated Pants, Spring Bag, Winter Bag, Workwear Shoes, Winter Outfit, Midsize Outfit, Quince, AYR, Ann Taylor, Amazon, Loft, Casual Workwear, Over 40 Fashion, Midsize Fashion

Top | Sweater | Jeans | Sneakers | Watch | Bag

Fit Tips: Shirt tts, L // Sweater tts, L // Jeans size up wearing 32

Winter Workwear, Workwear Over 40, Business Casual, Workwear Jeans, Winter Coat, Workwear Jacket, Lady Cardigan, Wide Leg Jeans, Wide Jeg Pants, Pleated Pants, Spring Bag, Winter Bag, Workwear Shoes, Winter Outfit, Midsize Outfit, Quince, AYR, Ann Taylor, Amazon, Loft, Casual Workwear, Over 40 Fashion, Midsize Fashion

Sweater | Jeans | Sneakers | Watch | Bag

Fit Tips: Sweater tts, L // Jeans size up wearing 32

Winter Workwear, Workwear Over 40, Business Casual, Workwear Jeans, Winter Coat, Workwear Jacket, Lady Cardigan, Wide Leg Jeans, Wide Jeg Pants, Pleated Pants, Spring Bag, Winter Bag, Workwear Shoes, Winter Outfit, Midsize Outfit, Quince, AYR, Ann Taylor, Amazon, Loft, Casual Workwear, Over 40 Fashion, Midsize Fashion

Top | Sweatshirt | Jeans | Sneakers | Bag

Fit Tips: Tee tts, L // Jeans tts but run long wearing large petite // Long sleeve tts, L

Winter Workwear, Workwear Over 40, Business Casual, Workwear Jeans, Winter Coat, Workwear Jacket, Lady Cardigan, Wide Leg Jeans, Wide Jeg Pants, Pleated Pants, Spring Bag, Winter Bag, Workwear Shoes, Winter Outfit, Midsize Outfit, Quince, AYR, Ann Taylor, Amazon, Loft, Casual Workwear, Over 40 Fashion, Midsize Fashion

Top | Blazer | Jeans | Shoes

Fit Tips: Blazer tts, L // Tee tts, L // Jeans run long tts, Large petite

Winter Workwear, Workwear Over 40, Business Casual, Workwear Jeans, Winter Coat, Workwear Jacket, Lady Cardigan, Wide Leg Jeans, Wide Jeg Pants, Pleated Pants, Spring Bag, Winter Bag, Workwear Shoes, Winter Outfit, Midsize Outfit, Quince, AYR, Ann Taylor, Amazon, Loft, Casual Workwear, Over 40 Fashion, Midsize Fashion

Top | Blazer | Pants | Pumps | Bag

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

Winter Workwear, Workwear Over 40, Business Casual, Workwear Jeans, Winter Coat, Workwear Jacket, Lady Cardigan, Wide Leg Jeans, Wide Jeg Pants, Pleated Pants, Spring Bag, Winter Bag, Workwear Shoes, Winter Outfit, Midsize Outfit, Quince, AYR, Ann Taylor, Amazon, Loft, Casual Workwear, Over 40 Fashion, Midsize Fashion

Top | Coat | Pants | Belt | Pumps | Bag

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

Winter Workwear, Workwear Over 40, Business Casual, Workwear Jeans, Winter Coat, Workwear Jacket, Lady Cardigan, Wide Leg Jeans, Wide Jeg Pants, Pleated Pants, Spring Bag, Winter Bag, Workwear Shoes, Winter Outfit, Midsize Outfit, Quince, AYR, Ann Taylor, Amazon, Loft, Casual Workwear, Over 40 Fashion, Midsize Fashion

Sweater | Coat | Skirt | Shapewear | Pumps | Bag

Fit Tips: Top tts, L // Coat tts, L // Skirt size up, XL

Winter Workwear, Workwear Over 40, Business Casual, Workwear Jeans, Winter Coat, Workwear Jacket, Lady Cardigan, Wide Leg Jeans, Wide Jeg Pants, Pleated Pants, Spring Bag, Winter Bag, Workwear Shoes, Winter Outfit, Midsize Outfit, Quince, AYR, Ann Taylor, Amazon, Loft, Casual Workwear, Over 40 Fashion, Midsize Fashion

Jacket | Top | Pant | Pumps | Bag

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

Winter Workwear, Workwear Over 40, Business Casual, Workwear Jeans, Winter Coat, Workwear Jacket, Lady Cardigan, Wide Leg Jeans, Wide Jeg Pants, Pleated Pants, Spring Bag, Winter Bag, Workwear Shoes, Winter Outfit, Midsize Outfit, Quince, AYR, Ann Taylor, Amazon, Loft, Casual Workwear, Over 40 Fashion, Midsize Fashion

Tank | Jacket | Pants | Pumps | Bag

Fit Tips: Jacket tts, 12 // Tank size up, XL // Pants tts, 12R

Winter Workwear, Workwear Over 40, Business Casual, Workwear Jeans, Winter Coat, Workwear Jacket, Lady Cardigan, Wide Leg Jeans, Wide Jeg Pants, Pleated Pants, Spring Bag, Winter Bag, Workwear Shoes, Winter Outfit, Midsize Outfit, Quince, AYR, Ann Taylor, Amazon, Loft, Casual Workwear, Over 40 Fashion, Midsize Fashion

Cardigan | Tank | Jeans | Pumps | Purse

Fit Tips: Jacket tts, 12 // Jeans tts, 12R

Winter Workwear, Workwear Over 40, Business Casual, Workwear Jeans, Winter Coat, Workwear Jacket, Lady Cardigan, Wide Leg Jeans, Wide Jeg Pants, Pleated Pants, Spring Bag, Winter Bag, Workwear Shoes, Winter Outfit, Midsize Outfit, Quince, AYR, Ann Taylor, Amazon, Loft, Casual Workwear, Over 40 Fashion, Midsize Fashion

Top | Pants | Pumps | Bag

Fit Tips: Blouse tts, L // Spanx pants size up if in-between wearing LP

Winter Workwear, Workwear Over 40, Business Casual, Workwear Jeans, Winter Coat, Workwear Jacket, Lady Cardigan, Wide Leg Jeans, Wide Jeg Pants, Pleated Pants, Spring Bag, Winter Bag, Workwear Shoes, Winter Outfit, Midsize Outfit, Quince, AYR, Ann Taylor, Amazon, Loft, Casual Workwear, Over 40 Fashion, Midsize Fashion

Top | Pants | Pumps | Belt | Purse

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

Winter Workwear, Workwear Over 40, Business Casual, Workwear Jeans, Winter Coat, Workwear Jacket, Lady Cardigan, Wide Leg Jeans, Wide Jeg Pants, Pleated Pants, Spring Bag, Winter Bag, Workwear Shoes, Winter Outfit, Midsize Outfit, Quince, AYR, Ann Taylor, Amazon, Loft, Casual Workwear, Over 40 Fashion, Midsize Fashion

Top | Blazer | Jeans | Pumps | Purse

Fit Tips: Blazer tts, 12 // Top tts, L // Jeans tts, 12R

Winter Workwear, Workwear Over 40, Business Casual, Workwear Jeans, Winter Coat, Workwear Jacket, Lady Cardigan, Wide Leg Jeans, Wide Jeg Pants, Pleated Pants, Spring Bag, Winter Bag, Workwear Shoes, Winter Outfit, Midsize Outfit, Quince, AYR, Ann Taylor, Amazon, Loft, Casual Workwear, Over 40 Fashion, Midsize Fashion

Top | Pants | Pumps | Bag

Fit Tips: Top tts, L // Pants, 12R

Winter Workwear, Workwear Over 40, Business Casual, Workwear Jeans, Winter Coat, Workwear Jacket, Lady Cardigan, Wide Leg Jeans, Wide Jeg Pants, Pleated Pants, Spring Bag, Winter Bag, Workwear Shoes, Winter Outfit, Midsize Outfit, Quince, AYR, Ann Taylor, Amazon, Loft, Casual Workwear, Over 40 Fashion, Midsize Fashion

Top | Pants | Belt | Shoes | Purse

Fit Tips: Sweater tts, L // Pants tts, 12R

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Winter Workwear, Workwear Over 40, Business Casual, Workwear Jeans, Winter Coat, Workwear Jacket, Lady Cardigan, Wide Leg Jeans, Wide Jeg Pants, Pleated Pants, Spring Bag, Winter Bag, Workwear Shoes, Winter Outfit, Midsize Outfit, Quince, AYR, Ann Taylor, Amazon, Loft, Casual Workwear, Over 40 Fashion, Midsize Fashion

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