Workwear on the Weekend?

work clothes for casual

Do you have a section of your closet that contains super-casual, outrageously comfy, weekend-only duds? And do you wear these items as a set, never mixing them with your dressier weekday garments? And if so, do you occasionally feel like you’re leading a Jekyll/Hyde life and wonder who the hell you are, stylistically speaking?

I’ve been there. Oh, friends, I’ve so been there. For ages, I thought I was required to wear skirts and blouses to work, but switch to hoodies and jeans on the weekend. And while there’s certainly nothing wrong with that – and, in fact, many women vastly prefer such a setup – it just didn’t FEEL right to me. I felt like I had two diametrically opposed looks going on, and it was messing with my sense of stylistic identity. Although I vastly preferred my weekday look, it seemed ridiculous to pull on a pair of heels and a dress for errands and Target-runs. And although my weekend garb was comfy and cute, it simply didn’t reflect the version of myself that I wanted to project.

I knew that my work week look was nailed, and that it was my maxin’ and relaxin’ wardrobe that needed revision. So I made some serious changes – both in inventory and attitude – and I feel like my look is consistent and unified at last. AT LAST! Here’s what I did, in case you’re feeling similarly disjointed and hoping for some guidance:

I created a new category: Lounge

So there are work outfits, and there are weekend outfits … and then there are the outfits I want to wear during a Netflix marathon while a purring tabby sits on my chest. I realized that I needed some items that would always be covered in Harriet-fur, and that could be reserved for nights (or afternoons! or mornings!) spent inside the house. Exclusively. I ended up downgrading a few casual pieces – joggers that had a tiny hole in the butt, sweatpants that were bought for sleeping but turned out to be too hot, track jacket with a minor sleeve stain – and relegated them to loungewear. This category never cross-pollinates with the rest of my wardrobe. (HM calls these items my pre-Js – the stuff I wear BEFORE my PJs. I don’t lounge in my actual PJs since cat hair-encrusted PJs means sleeping with a mouthful of cat hair. Which, for me, means not sleeping at all.)

I learned to juxtapose

What is the POINT of a weekend if you can’t wear jeans, right? But that doesn’t mean those jeans absolutely must be worn with sneakers and sweatshirts. In fact, juxtaposing some super comfy and traditionally casual items with dressier ones is a great way to until workweek and weekend looks. So a graphic tee and jeans with a blazer and heels. (Denim makes everything it touches feel more relaxed, and allowing jeans to be the single casual item in an otherwise dressy ensemble is a surefire formula for chicness.) Slouchy joggers with a structured jacket and statement necklace. Sometimes I’ll have more dressy pieces or more casual pieces in a mix, but it’s nearly always a mix. (Nearly.)

I tried wearing simple-but-dressy skirts with casual tops and accessories

Juxtapositions often orbit around denim, but dressy skirts can work in casual-dressy mixes, too. I keep solid-colored a-lines and pencil skirts in rotation for weekend wear, but pair them with my graphic tees and hoodies, or with slightly chunkier shoes, or more masculine styles of shirt or blazer.

I accessorized to the hilt

I am an accessory fiend, but for ages I would limit myself to my CZ studs and maybe a simple silver chain on the weekends. I’ve finally figured out that jeans and a white tee are far more fun with a giant necklace-pile laid on top, and that scarves can liven up any casual ensemble, and that heels might not be ideal for grocery shopping or mulching the garden but they add some fantastic sass to a coffeeshop-lounging outfit.

Now that I’ve forced a little crossover, I feel more self-assured when I dress for weekend outings: Instead of feeling formless and frumpy, I feel confident and chic. It’s not a formula that all women will want to embrace, but I find that mixing in a little workwear on the weekend is key to keeping my look consistent and unified.

Images courtesy J.Crew.

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for See Already Pretty’s disclosure statement for more details. Sustainable options are either used, handmade, made in the U.S., artisan made in non-sweatshop conditions, or made using sustainable/fair trade practices.

Originally posted 2009-06-02 06:05:00.

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32 Responses to “Workwear on the Weekend?”

  1. Christina Lee

    here here Sal! I pretty much did the same thing and feel sooo much better- not scared anymore if an old flame sees me at the grocery store 🙂

  2. elena-lu

    ive been married two years now and once married is when i realized that my comfy but not flattering weekend gear wasnt gonna cut it! i hadnt noticed how contradicting my workweek style and weekend style was until now so for the past two years ive been trying to do exactly what you described and having some success though im still not there yet! but im still trying to be more fluid in my style and not forget that i want to be fab not just monday thru friday! 🙂

  3. Legal Editor Mom

    I used to keep my career wardrobe totally separate from my weekend/casual, but no longer. I prefer a somewhat “dressed up” casual-chic look on the weekend. Even though it’s not quite the same as what I wear to work, I definitely look nice and not afraid to run into anyone! (I NEVER wear sweats or gym shoes.)

  4. Oranges And Apples

    Hi, great post and sound advice! I found your blog via your comment bits and bobbins, and love it!

    I also live somewhat of a Jekyll and Hyde life stylistically, but in a completely different way from how you used to! My personal style is colourful, young, sometimes a bit mad/silly and almost entirely thrifted, but I also work in a professional job and really could never wear ‘my’ kind of stuff to work.

    I used to wear something of a compromise, including some ‘me’ things in my work wardrobe, but this didn’t really work: I didn’t look smart, but I didn’t really look like my personal style either. Plus people I didn’t know would always think I was much younger than I was and treat me more junior than I was. Then I got promoted and I decided to really make an effort and dress more smartly. People now take me much more seriously, which may partly be the job, but I’m sure the professional clothes play a part. I’m even beginning to like the shirts and heels a little.

    But of course, I haven’t given up on my dressing-like-a-bowl-of-fruit ambitions. I only have two days a week to dress like that, and therefore make the very most of my weekends, when I dress up in a thrifted multi-colour way, just the way I like it!

  5. fashion herald

    I think I’ve finally got enough decent weekend wear so I don’t feel completely gross when going to the grocery store and laundromat. Hats are key for me on the weekend, as I don’t like to do jack to my hair!

  6. futurelint

    Since I work in an arts focused school, we have a pretty laid back dress code for teachers. I do wear jeans to work, but also tend to “dress-up” a lot. The only real difference between my work week clothing and my weekend clothing, is I can get a LITTLE more risque on weekends. Being young, I go out of my way to try to look professional and make sure my skirts go to my knees for work and my tops totally cover the ladies and aren’t too tight. On weekends I pretty much do the same thing but will sometimes wear slightly shorter skirts or not wear leggins under them or leave a button or two undone on my shirts. I feel so blessed, working at an arts focused school gives me so much wardrobe freedom! We can even wear hats indoors!

  7. Audi

    Sal, I swear we are twins separated at birth. I used to do the exact same thing; I felt like a vixen during the work week and a frump on the weekends. It wasn’t until I moved back to SF, where scarves are a necessity pretty much all the time, that I started to realize I could make my weekend looks a lot more interesting with a little accessorizing. Since then I’ve made it a point to keep my weekend style relaxed but still very much in line with what I wear during the week, and I’ve even started to scrutinize purchases of weekend clothes to see if they can jump the barrier into my workwear. Awesome post, doll.

  8. eednic


    I still struggle with my weekend wear. I’ve gotten better at it but for years I’ve been mostly unable to come up with anything casual/cute/comfortable/but also stylish and reflects my personality. Meh. I think my denim gauchos have helped, as have some of my Express items like my long white cotton vest and tunics. Accessories are helping too (I’ve recently been purchasing more jewelry and belts).

    I sometimes though will still stare at my closet completely befuddled. Maybe part of it is because I spend time actually planning the weekday outfits and leave the weekend to chance. Maybe I should consider doing a little weekend planning too.

  9. Jilliebeanie

    Timely post. I was just pondering this very thing about my style/wardrobe. I’m not a total slob on weekends, but improvements could certainly be made.

  10. jslewis27

    I am a die hard jeans girl, and I have to wear business casual during the work week. So usually, on the weekends, you cannot pry me away from my denim. I do try to cuten it up by pairing even my frayed at the hem jeans with bold, colorful tanks and embellished sandals. I found myself for a while living in zip up hoodies and my threadbare All Stars. My little sis forcibly dragged me out of my slump, and now my week wear and my weekend styles are more closely intertwined. My next goal is to work one of my Target via Goodwill specials skirts into a weekend ensemble. I did find my “go to” sandal for the season at payless…vibrant orange snakeskin with gold trim. (You have to see them to love them, lol).

  11. Jenn @ Workchic

    This is a great post and so true. We easily lose our personal sense of style on the weekends in an effort to be “comfortable” These are great tips for maintaining your stylish image and still enjoying your blue jeans.
    Also love these tips for anyone working in a casual office.

  12. Diana

    I agree wholeheartedly. I’ve slowly been getting rid of my casual items that were just too casual, and mixing up my weekend wear with my weekday wear. As I result, I feel much more confident and much less frumpy.

  13. C

    Oddly, I have was recently trying to do the opposite, seperate my work wear from my weekend wear. It seemed what should have been weekend wear (little tank tops and not as dressy jeans) were making their way into my work rotation. But, in all fairness, my weekend wear doesn’t contain much sweat pants or old t-shirts, mostly things too scandalous for work…

  14. Tina { Luphia Loves... }

    what great ideas! mix & match is def the way to go 🙂

  15. WendyB

    My Jekyll/Hyde feelings comes from wearing so much black during the day and so much color at night.

  16. rb

    I used to say “I have suits and sweats”, meaning work vs weekend. Usually I’d run into a problem when headed out of town for a weekend and not really wanting to do the sweats thing.

    I still have definite weekend only clothes because I have kids and don’t want to have to dry clean EVERYTHING but my weekend clothing is now almost as well thought-out as my weekday clothing. They tend to be cotton skirts (denim pencil or print a-line) and nice tops. If I wear a tee it’s not a basic T – there has to be something interesting and more dressy about it.

    I like your idea of wearing more accessories on the weekend. I have a tendency to put on the silver hoops and figure I’m all set.

  17. Katie K

    Here here Sal! When I started grad school, I also had a part time job working at a university librarian as a evening reference librarian and I had to buy a ton of business casual clothes. The whole idea of wearing my business casual clothes out to restaurants and bars was a huge style revelation for me. If you feel confident in a sweater when it’s with a pair of dress pants, why wouldn’t you feel equally confident when that same sweater and a cute pair of jeans and some fun accessories?

  18. Kristen

    all good suggestions…but with a n9 month old, dressing on the weekends includes barely any accessories and comfy jeans. i could use an updated shirt or two, though. 🙂

  19. lisa

    My office is incredibly casual and I veer towards dressy casual anyway, so my weekend wear and work week wear are roughly similar. The only thing is I’m more conscious of how much skin I’m showing during the work week, whereas for the weekend I might wear a halter top or a cute little sun dress. Also, I have a collection of worn-out scrub clothes that I wear only when lounging at home. 😛


    I have a few men's fitted coton shirts that are not ironed at all…luv the wrinkles (inspired by Watanabe show I saw)-wear with cute fitted t-shirt & nice pair of shoes…& banglesss! ~that's my weekend wear these days…

  21. Nadine

    I’m still a student so no working stuff: only casual/weekend clothing :)… but I have a lot of stuff I could also wear for teaching.

  22. Mademoiselle Frou-Frou

    i wear a lot of J Crew, so it works seamlessly from work to weekend. but then again, i can wear jeans to work and pretty much dictate my style.

  23. issa

    great post!! it’s funny because with my super casual dress code at work i’m usually the most dressed up person at work.. which used to not be the case.. jeans and a tshirt were the staple here.. then i finally decided it was time to make use of my wardrobe.. so my wardrobe actually stays the same for all 7 days… except the weekends i can throw in strapless and cut off shorts 🙂

  24. The Raisin Girl

    Schlumpy is an excellent word.

    I typically end up looking a little bit dressy every time I walk out of the house. I used to be a jeans-and-tshirt sort of girl, and I don’t know when that changed, but I don’t remember the last time I went anywhere in just a t-shirt and a pair of jeans. That goes for weekends, too.

    Of course, I’m in a pair of scrubs or sweatpants and a baggy sweater indoors, and I always have at least one overlarge button up and ruined pair of old jeans lying around that I can paint in.

  25. K.Line

    Hmmm, maybe I shouldn’t admit this, but I’ve decided to bring my weekend to the office! I now wear jeans most days (but fitted, dark denim) along with taliored tops and elegant accessories. I find it works all week long.

    Of course, if I’m meeting with the bigwigs I go dressy.

  26. AsianCajuns

    At work I can pretty much wear what I want (minus cut-offs and hoochie outfits)- which is dreamy, but I still try to be a bit more professional in the office than on the weekends. On the weekends I do dress for myself- and this often included heels and/or a great dress (brunchwear- woohoo- particularly dresses with a little stretch to fit in those last bits of eggs benedict). I think you are so right to encourage ladies to not get too stuck in dressing down for the weekends to compensate for stiff formal work wear during the week.

  27. kate

    great post Sal! I tend to do my hyper-Mad Men inspired pencil skirt and heels gear for work, and for the weekends go for a younger, more mod-inspired look – I’m a skirt girl too, but don’t do minis for work, and love to wear them at the weekend!

  28. Jess

    Great post- one of my favorite topics!

    I used to be the same way too- I had my nice clothes for work, then my play clothes for when I got home and on the weekends. The two occasionally woudl meet on casual Friday at the office where I would try to pair a nicer top and heels with my jeans, but otherwise they were pretty separate.

    Learning how to look nice but still be casual has been a long process for me- it's always been the most difficult for me. These days though I work from home full time so I have no dress code. The allure of wearing my schleppy jeans, sweatshirt and flip flops every day wore off pretty quickly- I felt like a sloppy college student all the time. I was wearing the same stuff every day and found the wear and tear coming a lot quicker!

    Now I'm embracing a more dressed up casual look even when I don't feel like there's a good 'reason'. Even if I'm just working from home all day, it feels good to wear actual cute shoes- even heels! It definitely changes how you feel for the better.

  29. exoticsexyfun

    whatever i style i wear for the weekdays i usually end up wearing the same style for the weekends

  30. Hanako66

    great post!!!

    I am pretty good about mixing my dressy and casual, but am recently working on "upgrading" my around-the-house-wear from sweats to cute cami's and dresses

  31. Tina (SoontobePhD)

    I too struggle with how to dress casually without looking dumpy on the weekends (and during the rest of the week while I work from home for that matter). Good advice. I've learned that adding big earrings or a large necklace and some great shoes are enough to liven up any t-shirt/jeans combo.