Reader Request: Casual Friday, with Style

Sweet reader Christen had this request:

I’d LOVE some advice on Casual Friday. Are there rules? Does the meaning of “casual” depend on how buttoned-up the normal dress code is?

Well, my dear, here’s the simple answer: Ask your HR rep. Any office that has a normal dress code will ALSO have a few guidelines for dressing appropriately on Casual Fridays. If you’re worried about getting busted for wearing your sweatshirt and sneaks, ask the authorities. Better safe than sorry, eh?

And here’s the convoluted answer, in case you’re not worried about actual, technical guidelines as defined by your employer: There are no universal rules for Casual Fridays. It really does depend upon the atmosphere and attitudes at your particular office. But maintaining a relatively consistent style all week and maintaining a relatively professional demeanor at all times can only serve to make a woman appear self-aware, responsible, and mature. S0 I’m not going to issue a ban on denim or scold anyone for dressing down on the one day when high heels and pressed shirts AREN’T expected at work. I swear I’m not. But I am going to offer some suggestions for making Casual Friday work a little more seamlessly with Formal Monday Through Thursday.

First I will indulge in a short list of donts. Again, these are MY personal guidelines. Your office may allow all of these donts, you may love nothing more than wearing them to work on Friday, and you can feel free to do so. But since I’m being asked for my opinion …

1. No sneakers: There are plenty of sneaker-like shoes that will present a far more pulled-together appearance than bona-fide tennies. And if you’re whining because your only pair of truly comfy shoes are your trainers, it’s time to expand your footwear wardrobe.

2. No ripped denim: OK, a little patch here and there is passable. But truly destroyed jeans? Save them for the actual weekend.

3. No sweats: In my humble opinion, sweatshirts are for cozy nights at home watching Buffy reruns, cleaning out the garage, and brisk morning jogs. Unless we’re talking a fitted, zippered track jacket or another, more structured top that just happens to be made of fleece, I advise avoidance.

Now, let’s do some dos, shall we? There are plenty of ways to look chic and stylish while still feeling comfy and casual on Fridays at the office. Here are a few of my favorite ways to make Casual Fridays work:


I have several pairs of jeans, but I seldom wear them. I do, however, save my OTHER denim pieces for Friday wearings. This jean jacket gets thrown into the mix often, as does my beloved denim miniskirt. Denim is, by nature, casual and there are plenty of ways to wear it without pulling on a pair of Levis. Utilize alternative denim items alongside funky, formal, or feminine pieces.


I advocate for smart jeans whenever jeans are worn. To me, smart jeans are dark, neat, not-destroyed, and fit your body type perfectly. No dragging hems, no sagging pockets, no gaping or constricting waistbands, and no rips or stains. Here, I’ve paired my dark-wash skinnies with a printed blouse and red heels. I’d never wear the jeans during the rest of the work week, but felt comfy and perfectly myself wearing this outfit to the office on a Friday.


I have amassed quite a collection of graphic tees over the years, and for ages I just couldn’t figure out how I wanted to wear them. I felt too dressed-down pairing them with jeans, and just bizarre pairing them with more formal pants. The answer, as is so often the case for me, was to throw on a skirt. I wear my tees with pencil skirts, full skirts, just about any non-pant in the closet will do.


Some folks maintain that leggings can be dressed up enough to be everyday officewear, but I feel that they’re a pretty casual bottom by nature. No matter how sophisticated your top and shoes, you’re going to look a little bit less than formal when they’re paired with leggings. But they’re comfy as heck, sleeker than most jeans, and ideal for casual office wearings. I’d take this jersey tunic and legging outfit to the office in a heartbeat … but only on a Friday!

As you can see, my basic formula is to introduce one or two very casual elements, and keep the rest of the outfit fairly dressy. Now remember: Dressy does not automatically equate to uncomfortable, friends. Or it shouldn’t. Mine your closet for pieces that are both refined AND comfy, and build your Friday outfits around them. Or just accept that total, squishy, toe-curling comfort should be reserved for Sunday mornings at home. Sporting a smidgen of structure and style on Casual Friday isn’t actually a sacrifice. You can have fun with your casual looks, and bring a few super-dressed-down items into the mix … but always remember that a consistent, polished style broadcasts a more confident, pulled-together you.

Originally posted 2009-09-04 05:36:00.

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29 Responses to “Reader Request: Casual Friday, with Style”

  1. smaro

    love the cargo pant, gladiator sandals and arty top..very effortless and cool. No such thing as casual Fri in our office. 🙁

  2. Sharon Rose

    Hi there-a really great post, I love a denim jacket and denim skirt (not together!) and I love your olive colour cargos! Have a good weekend!

  3. Mindy

    In your opinion, is there an age at which a person should stop wearing denim skirts, or are they appropriate for any age? (I'm not talking about minis.)

  4. Kathleen

    I dress business casual pretty much all week long. We have a more casual dress code during the summer, but we're still not supposed to wear jeans or flip-flops (though that hasn't stopped some people). I do wear denim jackets and the odd denim skirt every once in a while though.

    I love that purple blouse with the frayed green skirt outfit! Purple and green is one of my favorite color combos.

  5. Tina

    First, I love your outfit in the very top photo. It makes your legs look amazing.

    Second, thanks for the post topic. I really agree with all your Friday suggestions and tips. I used to work in an office that was very dress M-Th and then on Friday people showed up basically in PJs. I found it very disturbing, and everyone else thought it was odd when I showed up in jeans, heels, and a blazer.

  6. Meli22

    unfortunetly- graphic tees and leggings are not allowed in my office- EVER. No ripped denim, no stained anything, nothing with a logo/writing/graphics, no hoods, no hats. :/. And we're 'buisness casual' lol. I love your pics, the first is the most awesome thou!

  7. Sal

    Mindy: Great question! I think it really depends on the individual's style and body shape, so I'm reluctant to put a number out there … but I'll try to give a ballpark. I'd say by 50, a woman should consider denim pencil skirts that hit at knee instead of minis, even if she's got great gams. (Earlier if you're not comfy in a mini. Always consider your own style and comfort first!) At 60, I'd say switch over to something ankle-length. By 70, it's probably time to give up on denim skirts.

    Just my two cents, since ya asked. 😉

  8. Diana

    I love your take of Casual Friday. Most of my workplace have been pretty casual in general, but this will help out a lot once I get to a more formal workplace.

  9. Work With What You've Got


    I never thought of this. I am so anti cargo pants that it never occured to me, but it looks GREAT and I am adding cargo pants to my thrift shopping list!

  10. Courtney

    Thanks for the reminder! At my work, it's always Casual Friday, so it's great to have the encouragement to not turn into a schlump. And I love your cargo pant combo. I need to work up the nerve to try it!

  11. discount shopping

    I suppose an even worse idea for a 'casual friday' would be ripped sweatpants with an equally ripped sweatshirt…

    Love the photographs, the ideas, and the creativity behind each. Fantastic job!

  12. Hanako66

    such a great post! I have casual every day (unless I have a meeting) and it is easy to get boring…you have casual friday down!

  13. lisa

    Such great tips and sensible advice, Sal! I definitely agree with your list of don'ts.

    My office doesn't have a real dress code so every day is casual day. I actually dress according to a reverse trajectory: Monday blahs and sweaty salsa nights on Tuesday and Wednesday make me dress down a notch, but Thursday and Friday I'll have a bit more fun with what I'm wearing because I might be going out for cocktails after work. 😉

  14. K.Line

    Terrific suggestions. I have to say I'm dressed "casual Friday" 4 days a week (I exaggerate but, if I feel like it and the weather sucks and I don't have client meetings then I do my own thing.) For me casual always means chic – just not fussy. I wear skinny jeans often but they are all dark denim and I pair them with elegant shoes. I usually wear a jacket or cashmere with them and I accessorize the fancy in.

  15. Missy D

    So glad I stumbled onto your blog! It is fabulous!

    One question… where did you get those super cute red shoes in the denim picture? I love them!

  16. Couture Cookie

    Great post! I quit my office job (thank God!) but we were lucky enough to have a casual dress code all week long! Sweats, hooker dresses, ripped jeans… anything was OK as long as we kept a suit in our offices! Sometimes clients called us, "hey, I'm in the lobby, can I come up?", and we all ran to the restrooms to change!

    I'll send your blog to all my 9-5 working friends! 🙂

  17. isleen

    Sal, I'm going to have to respectfully disagree on the denim skirts. Long denim skirts are appropriate at any age! And as far as shorter skirts, consider your knees, which will vary from woman to woman. If your knees look like you need to pull up your pantyhose and you aren't wearing any, it's time to look for skirts that skim past that spot. Or consider hosiery. I saw a very stylish 80-something last week in a mini with dark stockings and she looked fab. Super-short denim minis are of course, only appropriate on those under 25.

    I work out of my home, so I can wear whatever I want (in theory) but I've found that it is impossible for me to get anything done in sweats. Putting on proper clothes is the signal to my brain that, yes, we are going to accomplish things today.

  18. SwanDiamondRose

    i love this outfit "SMART JEANS WITH A SLIGHTLY DRESSY TOP". and love denim. i do wear ripped up denim but i do love smart polished denim too. i sweats… ya, those just make me feel lumpen. i never understaood the freedom of those, it's more like mushyness. but other people canw ear them.

  19. dapper kid

    Excellent post 🙂 I really do think a denim jackets are amazing, you can sling it over a suit in place of the blazer and it just works. And your smart jeans with dressy top look is wonderful. Is it weird that I do Formal Fridays at university? I see everybody else dressing down throughout the entire week, so I wear a full suit/pocketsquare/tie bar combination on fridays. Hope you are having an absolutely beautiful day 🙂

  20. emma wallace

    My favorite outfit was the cargos/artsy top! I love cargo pants and am never sure how to chicly wear them.

  21. Vered - Blogger for Hire

    I happily work from home, so no casual Friday issues for me. I enjoyed this post though, and those outfits are creative and very appropriate for most relaxed office environments.