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When you are in the corporate work field or your work dress code is Business Casual, Casual Friday permits you to go a bit more comfortable. The safest way is to go for a typical work outfit that meets the dress code and swap one piece for a casual one. Read this post to create looks beyond the typical jeans and T-shirt.

  1. The Anatomy of Great Casual Friday Outfits
  2. You Can Look Great on Casual Friday with Flat Boots
  3. When Casual Friday Is a Dressing Nightmare …
  4. … go wild for Casual Friday
  5. Wear a Retro Style Dress with a Chanel-inspired Jacket
  6. Mix Rock’n Roll Edgy with Classics for a Twist
  7. Street Chic Casual Friday Look with Sweatpants
  8. Can You Wear Sweatpants to Work?
  9. Jeans Skirt with Baseball Jacket for Casual Friday
  10. Other Pieces to Substitute for a Blazer
  11. How to Style a Cheap Trendy Dress to Look Professional
  12. Dress a Little Black Dress Down
  13. Wrapping Up the Best Outfit Ideas for Casual Friday


The Anatomy of Great Casual Friday Outfits

A Casual Friday look beyond the classic jeans-sweater recipe is composed of closet “basics”. For instance, a straight skirt, a sweater, denim jacket and tall riding boots. It’s a goto styling recipe that works with any knee-length or slightly above the knee pencil wool skirt, no matter whether it is made from tweed, has a houndstooth, glencheck, or tartan pattern. In the example below, the jacket the statement with its sequin patches. The look would also work well with a plain jean jacket and for winter-to-spring transition outfit with a white one. Instead of the all American jean jacket, a leather bomber or biker do the trick too.


You Can Look Great on Casual Friday with Flat Boots

On a day with fresh snow, flat classic tall boots are a Must when you have to park in an unplowed parking lots. They are also very versatile to style. See this guide on wearing tall boots in great style.


fashionista in American Classic winter outfit with denim, straight wool skirt, flatt knee high boots and turtleneck sweater
Side view of Casual Fiday look


business casual mature woman in oversize jean jacket, pencil skirt and tall black boots
Back view of the look


Nicole in American Classic Casual Friday look with tall boots
Outfit details: GNW tights, Banana Republic above the knees wool skirt, Hermes collier de chien bangle, citrin statement necklace, Tesori cashmere turtleneck sweater (all own) and patched sequin denim jacket c/o StyleWe



When Casual Friday Is a Dressing Nightmare …

Do you like to dress up, but there is a Casual Friday culture at your office? You are not a jeans gal, but don’t want to break the spirit? Thus, you struggle every Friday whether to wear the jeans or to exclude yourself from the pack.

… go wild for Casual Friday

Try this solution of the problem. Take Casual Friday as an excuse to wear something more wild than you normally wear. The possibilities are endless. It can be an extreme color piece or a leopard print skirt with otherwise office appropriate clothing or even these dressy leather shorts with an oversize sweater. Or just add an item that expresses your personal style.


Casual Friday outfit idea with oversized vest, knee length skirt, silk shirt, belt
Front view Casual Friday outfit with oversize sweater vest


casual Friday outfit idea with button down shirt, hounds tooth vest, plaid skirt, belt
Outfit details: Burberry plaid skirt, suede with gemstone buckle belt, modernist earrings, Sam Edelman bucket shoulder bag, Hermes collier de chien bangle, studded ankle strap pumps, Hipstik pantyhose, silk shirt c/o LilySilk and watch c/o Nordgreen


See the seven days skirt challenge for more separates outfit ideas.


Wear a Retro Style Dress with a Chanel-inspired Jacket

The outfit below features a 1940s inspired floral dress with a Coco Chanel type inspired quilted leather jacket. It’s a very eclectic personal style outfit.


retro style dress, belt and jacket as one of the Casual Friday outfit ideas
Front view midi floral dress with quilted leather jacket


1940s floral print midi dress
Outfit details: Self-sewn 1940s inspired floral print midi dress, Gucci enamel belt, Hinge quilted Chanel inspired cropped leather jacket, Steve Madden Kelly green pumps, Hermes Constance shoulder bag, modernist long dangling earrings, Hipstik pantyhose



Mix Rock’n Roll Edgy with Classics for a Twist

Try classics with a twist. One of my favorite twists is adding elements of Roll’n Roll. I love the combination of edgy (e.g. biker jacket) and classic (sheath, sling backs, pearls, diamonds, etc.).

Pro tip: Try a leather jacket in a different color than black as a substitute of a blazer for a classic with a twist work outfit.

stylist in striped sheath with cream jacket
White Graham & Spencer biker jacket with Calvin Klein striped sheath dress, statement bag and Anne Klein snake print sling back

Street Chic Casual Friday Look with Sweatpants

My regular readers know that I am not a big fan of real suits. Real suits look lovely on young women and give them a great professional look. However, you need to know and pay attention to how to wear a suit and not look old. As a matter of fact, on mature women, real pants or skirt suits often look conservative, and Old Lady.

When I have to wear a suit, I go for an unmatched suit that I put together from items of my closet like the fake suit or the fake short suit.

A frequently asked question is



Can You Wear Sweatpants to Work?

When you work in a casual work environment with Casual Friday culture, and hold a position without client interaction, you can wear sweatpants with a blazer as an unmatched suit. Add a crisp button-down shirt, blouse or professional looking sweater and heels. Keep accessories professional (e.g. diamond studs with pearl necklace and gold color watch). See more examples of how I wear my athleisure.

You can wear sweat pants with a blazer as a fake suit for work. #CasualFriday Click To Tweet

The three stripes on the leg of these sweatpants give them a tuxedo-pants or military formal uniform-pants like vibe. Keep everything in black and white for an elegant classic look. The outfit is fashion-forward because black and white is a hot trend to wear right now.


over 50 years old fashion blogger wearing an unmatched suit of sweat pants and blazer for work on Friday
Back view of Adidas pants and hounds tooth blazer look


mature woman dressed in an athleisure pants and business casual jacket accessorized with pearls
Front view of fake suit office outfit with Adidas athleisure pants, hounds-tooth blazer, black turtleneck, Harley Davidson booties, BCBG statement belt, three string different size pearl necklace, and Akoya saltwater one size of pearls pearl necklace c/o The Pearl Source


You can find an ultimate guide to styling athleisure at the link.



Jeans Skirt with Baseball Jacket for Casual Friday

A denim skirt is a great in a casual work environment or setting. The skirt should be straight and have a professional length.

When wearing a baseball jacket for Casual Friday, the material and quality are key. It should serve a similar function as a blazer. Pay attention to not style these items like a high school gal. It is all about looking mature and knowing what you are doing when you put your outfit together. To achieve this goal, the look bases on the repetition of each color. The scarf picks up the color of the jacket’s sleeves and two colors of the T-shirt. The turquoise buckle western belt matches the turquoise suede fall sandals. Thus, the outfit appears posh casual and well pulled together.


midlife woman in striped T-shirt
Michael Kors leather baseball jacket with Kate Moss for Longchamp bag, Nicole suede fall sandals, Kieselstein Cord belt, western buckle, geometric print scarf (all own) and striped T-shirt c/o Marine Layer. Review of this Marine Layer T-shirt


The next inspiration shows how to wear the baseball jacket jean skirt combination in winter.

stylist in utility jacket with denim skirt
Michael Michael Kors baseball leather jacket, Oliveo denim skirt, Kieselstein Cord belt and buckle, cashmere wool GNW Luxe sweater, statement necklace, tights, and heeled ducks



Other Pieces to Substitute for a Blazer

The next inspiration uses a biker jacket instead of a blazer and a jean skirt instead of a pencil skirt.

Denim skirt with tailored leather jacket for Casual Friday
Front view jean skirt with biker jacket


Casual office outfit with biker jacket and jean skirt
Bebe leather jacket over GNW Luxe wool cashmere sweater worn with denim skirt, blue tights, Gucci belt, statement necklace and heeled ducks


fashion blogger in denim skirt with Andrew Marc motorcycle shearling jacket
Andrew Marc shearling motorcycle jacket with long scarf tied in a European loop, head band, denim skirt, tights, heeled ducks, and Michael Kors leopard print satchel


The next inspiration gets a bit closer to the usual jeans with sweater idea of an Casual Friday outfit.

statement belt
Zoom-in on the statement belt


Manolo Blahnik booties
Details of the booties


winter casual Friday outfit idea with denim skirt and turtleneck sweater
Oliveo denim skirt with Ann Taylor cashmere sweater, Manolo Blahnik booties, pantyhose and statement belt


The next Ccasual Friday outfit idea features the jean skirt with T-shirt. The pumps keep the look work appropriate.

midlife style blogger in classics with a zipper twist for Casual Friday
The Limited striped top with zipper details on the shoulders, Oliveo denim skirt, peridot pearls statement necklace, and L.K. Bennett pumps. You can find another example of how I styled the striped top at the link.


style blogger Nicole in denim skirt with striped shirt and trench coat
Outfit details as above plus Burberry Brit trench coat, as outerwear

Note that the looks shown in this section, all also work with jeans instead of a jean skirt.


How to Style a Cheap Trendy Dress to Look Professional

The typical floral prints for summer are printed on white. These prints often fail to look professional. However, a dark background in another color than the usual black (which seems the second often choice to ground a floral print) can make a great Casual Friday look expressing your personal style.


fashion blogger over 40 in abstract floral and paisley print look
Trendy dress


fashion in a fashion forward A-line dress summer office look
Side view of cheap trendy dress


style blogger in a trandy dress styled as an outfit idea for Casual Friday
Shein abstract floral and paisley print dress, Kieselstein Cord belt, Hermes H-buckle, Hermes collier de chien bangle, L.K. Bennett patent leather wedges, 3.1 Philip Lim bag, pantyhose, wooden sports watch c/o Jord, and jade best girlfriends bracelet c/o Chico’s


This dress actually has an A-line cut, which is tricky to style when over 40. The hem namely falls like the tail of a Mermaid (see side view photo above), which may easily look too cute and/or girly. While this style is fine for young women on a weekend, it is too casual for work at any age, even on Casual Friday. However, using a simple styling trick namely accessorizing with a belt gets the width under control. Adding pantyhose and dress shoes makes the dress work appropriate.

Attention: Whenever you gather fabric with a belt, the hem looks about 2 inch (5 cm) shorter than it actually is when worn loose. When the length gets too short to look right, one of these cool underskirts may do the trick to provide the right length. 😉

Pro tip: When you wear a cheap/fast-fashion trendy item, pair it with some more expensive classic pieces to look great in fashion over 40.

Mix cheap and expensive pieces for a great outfit. Click To Tweet

What about a denim dress?

blogger in denim shirt dress
Liz claiborne shirt dress with side slits. The Kieselstein Cord belt gives shape to this straight shirt dress. Shoes: Liz Claiborne, sunglasses: D&G Madonna




Dress a Little Black Dress Down

Add a jean jacket and slides to a LBD.

stylist in casual posh little black dress for Thanksgiving
Great Northwest denim jacket, Dior silk neckerchief, statement belt, Jord bamboo watch, Covered Perfectly boat-neck little black dress, Matisse embroidered slides c/o Soft Surroundings, tan suede purse c/o Uno Alla Volta



Wrapping Up the Best Outfit Ideas for Casual Friday

Stay within the limits of your work dress code with respect to cleavage coverage, sleeve length, legwear and shoes. When you wear something different than the HR approved jeans and T-shirt, stay close to the dress code with one item more casual or use a slightly more casual version of the approved attire, for instance, a biker or bomber jacket instead of a blazer or cardigan, a jeans skirt instead of the jeans.


Photos of me: G. Kramm

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