Casual Friday sucks.
October 30th, 2007 @ 5:01 am

Every Friday is unofficially Casual Friday at my office. And every Friday I come to work in slacks and heels while my coworkers are wearing jeans and t-shirts. Every six months I’ll change things up a bit and wear jeans with heels. But for the most part I’m all about the slacks.

It’s not that I’m against Casual Friday or being casual in general. Heck, I can wear yoga pants with the best of them. It’s just that I don’t own anything appropriate for office casualness. I’m pretty sure my Old Navy yoga pants and the thefind.com shirt I got for free at BlogHer won’t cut it.

I try to spend a limited amount of money on my wardrobe. Since I work full time in an office setting, my wardrobe budget is spent on the clothes most needed. Which is where the slacks and heels and lack of jeans and tennis shoes come in.

Not only is my casual wardrobe lacking, my knowledge on how to wear jeans and tennis shoes is even more lacking. I see ladies around town in their jeans and tennis shoes and I think about cute (and comfortable) they look. But for me, I just can’t seem to pull that look off.

Maybe it’s because I’m not sure what type of shirt to wear with jeans and tennis shoes. Can you wear a cute little red top with jeans and tennis shoes? I don’t think you can, right? If you can’t wear something like this with tennis shoes, then what kind of shoes do you wear it with? I have some old black loafers, but they seem a little wrong to wear with jeans even though I do it.

Summertime is much easier. You can always wear flip flops or cute open toed flats. Winter is just more limited. One more reason to hate winter.

The King, my Sweet Babboo and I are flying out to visit my family this coming weekend. Packing begun last night since I’m now responsible for the packing for myself and my child. Plus all of the Christmas presents for my family and (iron on) baby gifts for my new (unborn) nephew. My problem is that I’ll be packing slacks and heels for these three fun-filled days at my folks house. Dude, they are all going to look at me like I’m some sort of tool playing out in the yard with Babboo, or riding a 4-wheeler with loafers or heels on.

How do I explain to my friends and family that the reason I’m so over dressed is because I’m too poor to bother spending money on casual clothing that I’ll only wear when I’m visiting them?

I figure I have four options:

  1. Own the fact that I’ll be wearing heels the entire trip and looking like an idiot.
  2. Own the fact that I’ll be wearing yoga pants and tennis shoes and looking like an idiot when I run into people from high school that think I always dress this casually when on vacation.
  3. Suck it up and buy a pair of $30 casual shoes and try to figure how out how to wear them with my current tops.
  4. Suck it up even more and just wear my flip flops, even though it’s the dead of winter where my family lives and I’ll probably die from frostbite.

It shouldn’t be this hard. Dressing casual should be just that…casual. This much thought shouldn’t be put into being comfortable in what you’re wearing.

I hate being me.

So tell me, what do I do?* What shoes do I wear with jeans?

*And please don’t tell me to buy new clothes. Really. I have a mortgage on a house I don’t even live in yet. Plus, we just bought a fridge, dishwasher and washer/dryer this weekend. I think I can swing some new shoes from Ross or the Shoe Pavilion. But that’s about it.

I rock

47 Comments

  1. Gravatar Icon

    Carrie
    said,

    October 30, 2007 at 6:20 am

    Two words: ballet flats.

    There ya go!

    Isabel:  I am happy to report that I found some super cute black ballet flats for $19.99 at the Shoe Pavilion last night after I wrote this post.  Hooray.  Now I just have to get used to wearing something without a heel! 

  2. Gravatar Icon

    Sara
    said,

    October 30, 2007 at 7:30 am

    I just went through this! I went to Sports Authority and bought some new sneaks. They are just like these:
    http://www.shopadidas.com/product/index.jsp?productId=2650449&shopGroup=R&cp=2019628.2039726.2039529&view=all&parentPage=family&colorId= except they have pink stripes on them. I love them and I get TONS of compliments on them. Which is weird since I really never look down at my shoes!

    Do you have jeans? If so, you are halfway there. I had to buy those too.

    Good luck!

  3. Gravatar Icon

    Loralee
    said,

    October 30, 2007 at 8:59 am

    Skimmers are really cute. The American Eagle brand at Payless make me happy.

    I also like having a stacked heeled loafer with jeans. It gives your leg a bit of lift. I love Mudd, if you can’t tell.

    You can absolutely wear both tops with jeans, but I would avoid tennies with them because those tops need a dressier shoe.

    You could be able to swing a rugged mary jane they are really comfy.

    Just some thoughts.

  4. Gravatar Icon

    LaLa
    said,

    October 30, 2007 at 10:47 am

    I’m with Carrie. Ballet flats.

    I always look a bit odd with tennis shoes as I like to wear jewellery and it doesn’t really match trainers.

    Hopefully you can find some that are simple but warm enough for you.

  5. Gravatar Icon

    velocibadgergirl
    said,

    October 30, 2007 at 11:33 am

    Ballet flats sound good, and you can most likely get some really cute shoes at Target or Payless for well under $30 that look very nice.

    In fact, I just went to Payless’s website, and they’re advertising all flats for $19.99 :D

    http://tinyurl.com/34kbr8

    http://tinyurl.com/38f3by

    http://tinyurl.com/2kxhgz

  6. Gravatar Icon

    Stephanie
    said,

    October 30, 2007 at 12:11 pm

    I am with you on this one. I rarely wear casual clothes just because I don’t want to waste the money. But I have work out clothes. So my options are work or workout. They don’t cross very well. But at least I have sneakers.

    Typically I wear one of two pairs of jeans with a regular work top and then a pair of work heels. Then if I am going super casual I wear my sneakers with a random t shirt from my college years. No kidding.

    I think Ross is the best bet for a cheap pair of ballet flats though. Usually you can find them for 14.99 ish. I don’t have any because I feel stumpy in them, but perhaps I need to invest also.

    Isabel:  I went to Ross last night after I wrote this post.  I didn’t find anything for me, but I found The King a pair of the new Simple eco shoes for $19.99.  He loves me for it. 

  7. Gravatar Icon

    Jess
    said,

    October 30, 2007 at 12:49 pm

    I have about 10 pairs of ballet flats and skimmers that I can wear with a pair of jeans and every top imaginable.

    Right now Old Navy has really inexpensive ballet flats and skimmers (ballet flats made of canvas), and they’re cute.

    I’d say spend the 30 bucks, buy one pair of brown and one black, and then you’re set. Wearable with any top, and any pair of jeans.

  8. Gravatar Icon

    Anna
    said,

    October 30, 2007 at 12:53 pm

    I have to agree 100% on the ballet flats. I found a pair of leopard print ones on clearance at Target for $4.97. I wear them with just about everything.

    Target has a great selection right now for $12.99 or less.

    Isabel:  I forgot that I own those leopard print shoes from Target.  Only I bought mine for full prize.  And a size too small.  They hurt. 

  9. Gravatar Icon

    Abbie
    said,

    October 30, 2007 at 1:18 pm

    This is my story right here. There’s no niddle ground for me, it’s either an old pair of jeans and tshirt or my professional work clothes.
    Sometimes I throw on some heels with my jeans and a cute jacket to top off the tshirt…I don’t know, but I guess that works?

  10. Gravatar Icon

    Carrisa
    said,

    October 30, 2007 at 1:18 pm

    Maybe you need to make another trip to the Goodwill and look for casual shoes and jeans. Or cheap shirts to make iron ons for yourself.

    I’ve still got a green Dove t-shirt that I stole from BlogHer. It’s a medium. I can send it your way.

  11. Gravatar Icon

    bethany actually
    said,

    October 30, 2007 at 1:23 pm

    Ballet flats, or classic black or brown boots!

  12. Gravatar Icon

    Sarah
    said,

    October 30, 2007 at 1:26 pm

    I will jump on the ballet flat bandwagon because they are affordable and adorable (and you can, or could earlier in the year, get some cute ones at kohls) but eventually it will be too cold and too wet for those kinds of flats. In my cold toed opinion.

    I think you need some kind of hybrid leather shoe. My vote is for danskos or a dansko knock off if you’re on a budget (the professional style) BUT I know they’re not for everyone. Although you can totally wear them to work and on the weekends.

    Skechers has a lot of cute leather shoes that are not sneakers. Maybe something like this?
    Or this from piperlime? Gold shoes go with everything. And they are cute now…not golden girl.

    My last thought is some kind of fall/winter wedge that would maybe even allow for non-casual days. Like these or these.

    Ok, I have mis-guided enough. Good luck!

  13. Gravatar Icon

    dee
    said,

    October 30, 2007 at 2:11 pm

    I was going to say to find some cute ballet flats, but it seems everyone else has already said that. You can get them pretty cheap and they can be worn with jeans or dress pants (if you get the right kind).

  14. Gravatar Icon

    Nic
    said,

    October 30, 2007 at 2:12 pm

    I have a very casual job. I wear jeans or something of that sort most days. Today I’m in this http://www.jcrew.com/images/nov299/emstyle/88702_GY6791.jpg these http://www.jcrew.com/images/nov299/emstyle/85638_BK0001.jpg and http://content.nordstrom.com/ImageGallery/store/product/MediumLarge/12/_5388352.jpg

    I LOVE ballet flats. They go with everything and make things super cute, and you can even wear them to work. Also, that red shirt is perfect with jeans. If I were going shopping, I’d get these http://www.target.com/Mossimo-Daven-Patent-Ballet-Flats/dp/B000PRYF22/qid=1193753080/ref=br_1_5/601-6478617-4196129?ie=UTF8&node=3429561&frombrowse=1&index=tgt-mf-mv&field-browse=3429561&rank=%2Bdaterank&rh=&page=5
    http://www.kohls.com/kohlsStore/shoes/womens/flats/PRD~240409/Croft++Barrow+Kerri+Ballet+Flats++Wide.jsp

    When in doubt, I always go to this site to see what people are wearing and where they bought it http://frugal-fashionista.blogspot.com/

  15. Gravatar Icon

    Marriage-101
    said,

    October 30, 2007 at 2:12 pm

    If you want ballet flats, you can get cute cheap pairs at Old Navy (or at least you could back in Aug. when I bought mine) for $10. But what about boots? Do you own any black boots? Those look fab with jeans, they’re just country enough to be out in the country, and not overly dressy like a pair of cute heels. BTW, do you have a pic of your heel collection? I love seeing other people’s shoe collections! And no, I do not have a foot fetish…maybe just a shoe fetish, but I’m too cheap to buy my own.

  16. Gravatar Icon

    Sara
    said,

    October 30, 2007 at 2:25 pm

    I have a totally different senerio than you, as I work in a ultra casual office and wear jeans everyday—or cords if Im feeling really dressy. I would wear both of those shirts you posted with jeans in a heartbeat… mostly because I only own about 2 pairs of dress slacks.
    I have never got into the ballet flat thing as it always seems my foot is exploding from them and I never wear the tight sock or stocking with them. I do have 2 pairs of boots that have lasted years and years and that I wear with jeans all the time. I have a brown pair and a black pair and between them, I am pretty much covered when it comes to footwear in a semi-casual-not-yoga-panted situation. Good boots aren’t cheap, but will last 4-evah. My brown Steve Madden’s are 6 years old and have years ahead of them, and my black Nine west boots are about the same age, but need replacing this season–if I can find a worthy replacement.

    Isabel:  Um yeah, I forgot that I own a couple of pair of cute black boots.  They might work.  Right? 

  17. Gravatar Icon

    Janssen
    said,

    October 30, 2007 at 2:35 pm

    My office, like Sara’s, is ultra casual (we’re talking shorts and flip flops or sweats and basketball shoes every day of the week). I probably dress up the most of anyone, but I do wear jeans almost every day, just with a semi-nice top and non-tennis shoes. I wear this pair of shoes (http://www.amazon.com/Unlisted-Womens-See-Slip-Black/dp/B000FF96S2/ref=sr_1_19/104-9447758-4362346?ie=UTF8&s=apparel&qid=1193754816&sr=1-19) almost daily because they look good with skirts or jeans and transition nicely between casual and dressy (and I bought them at Ross for about $14). Good luck! And have a fun trip!

  18. Gravatar Icon

    Rhi
    said,

    October 30, 2007 at 2:51 pm

    I’m with the Ballet Flats too. I usually, on casual Friday, wear nice jeans and a blouse with heels. SO THERE! I’m not into jeans with tennis shoes. I think tennis shoes are to work out in, and I don’t work out, so I have no need for them (but still have two pairs). Anyway, I recently got these cute keds,http://www.zappos.com/n/p/dp/27100381/c/5578.html which WERE NOT $45 something, but only $20. Cause I had a coupon :)

  19. Gravatar Icon

    Alison
    said,

    October 30, 2007 at 2:54 pm

    I’m the same way when it comes to tennis shoes and jeans….everyone else looks perfectly normal and I think I look dumb….
    I agree 100% with the ballet flats….I got my first pair over the weekend, for $10!, and have worn them the last three days…with jeans, with dress pants….and mine are leopard print….black would go with anything!
    I’d say the only down side is if you have longer pants that could be worn with heels, the flats might mean having pants dragging on the ground….or having to hem all your pants….

    Isabel:  Yep, my pants are all super long to accommodate for the heels.  I have one pair of “short” pants that will work with flats.  Hooray!

  20. Gravatar Icon

    Vesper
    said,

    October 30, 2007 at 3:12 pm

    I’m going to have to go with ballet flats, or puma like looking shoes, especially in weird colors. They are just so cool looking who cares what else you are wearing?!? You don’t have to actually go puma, you can get plenty of knock off look alikes at places like payless and target, and they are COZY. These actually look pretty cozy and cute and not too casual :http://www.payless.com/Catalog/ProductDetail.aspx?&TLC=Womens&SLC=WomensCasuals&BLC=WomensCasualsSporty&Width=Regular&ItemCode=56383&LotNumber=056745&Type=Adult&Popularity=333&DescriptiveColor=Black

  21. Gravatar Icon

    Durga
    said,

    October 30, 2007 at 3:15 pm

    People have given u some good advice. Ballet flats/ even the ones made out of canvas- those look good and are comfy.
    You could wear the tops in the pics u’ve got there with ur jeans.

    If I’d known u were too poor to buy casuals…I would have sent u something for ur bday. Now I know for next time. :)

  22. Gravatar Icon

    Ella
    said,

    October 30, 2007 at 3:18 pm

    Hi Isabel -

    I haven’t comment in a while but I’m still here and this post needed an answer.

    Okay, both shirts you referenced can be worn with jeans! Just wear ballet flats or boots to dressy it up but it won’t look like your going to the office. Check these out:
    http://www.payless.com/Catalog/ProductDetail.aspx?&TLC=Womens&SLC=WomensBoots&BLC=WomensBootsClassic&Width=Regular&ItemCode=56879&LotNumber=057972&Type=Adult&Popularity=283&DescriptiveColor=Multi

    or these: (low boots are in this season and these come in brown and black)

    http://www.payless.com/Catalog/ProductDetail.aspx?&TLC=Womens&SLC=WomensBoots&BLC=WomensBootsTrendy&Width=Regular&ItemCode=56722&LotNumber=056724&Type=Adult&Popularity=426&DescriptiveColor=Brown_Croco

    or these sporty ballet flats!

    http://www.payless.com/Catalog/ProductDetail.aspx?&TLC=Womens&SLC=WomensStory&BLC=WomensPromoFlats&Width=Regular&ItemCode=58835&LotNumber=058177&Type=Adult&Popularity=382&DescriptiveColor=Black

    I know that these are expensive (the price of a washer) but I just wanted to show you the style:

    http://www.piperlime.com/browse/product.do?cid=16995&pid=541589&scid=541589002

    So just pick up a pair boots (totally winter proof) and wear them proudly with your cute tops and jeans. Done!

    Hope this helped!

    -Ella

  23. Gravatar Icon

    janet
    said,

    October 30, 2007 at 3:21 pm

    I belong to the year-round flip flop club. Who cares about a little frostbite?

    Also…what about jeans + heels + red shirt? That would look perfect!

    Isabel: Yeah, now I need to get over my jean/heel phobia.  I feel like I’m just too old and plain to pull that look off.  I have issues, clearly. 

  24. Gravatar Icon

    Vesper
    said,

    October 30, 2007 at 3:25 pm

    I forgot to mention…Ugg type boots (and their many many knock offs) are both cozy and appropriate casual shoes in dead of winter situations…they go well with sweaters too..and you don’t have to always wear them over jeans..I have a short pair and a long pair to wear either over or under jeans..they are great for kickin it!

  25. Gravatar Icon

    alison
    said,

    October 30, 2007 at 3:34 pm

    What about a pair of those cute flats everyone is wearing right now? I’m pretty sure you can get a pair of those for $15 at Payless or somewhere similar. In my experience you can wear those with jeans, or with some of your more fancy work attire. Just a thought. Enjoy your visit home, and your early Christmas.

  26. Gravatar Icon

    Danielle
    said,

    October 30, 2007 at 3:48 pm

    Looks like you’ve got lots of good advice already - not much more I can offer - except that I feel your pain! I have been wearing a pair of black Clarks mary janes (that I found at the outlets) with my jeans lately. I wish I could pull off the ballet flat look…I own a few pairs, but my pants bunch up un-flatteringly (is that a word?) at the bottom. Maybe I could wear them with capris, but of course, capri season is over. Also, I feel so squatty in flats (this happens when you are only 5′ tall).

    Oh, also, I totally think you could wear that cute red top with jeans and heels!

  27. Gravatar Icon

    Danielle
    said,

    October 30, 2007 at 3:51 pm

    Ok - I just saw your reply to janet’s comment above - you are NOT too old or plain for that look. I think jeans + heels = HOT.

  28. Gravatar Icon

    heels
    said,

    October 30, 2007 at 4:00 pm

    I agree with Danielle- Jeans+heels=hot. Totally. And you could pull it off with either shirt that you had pictured in the links above. I think a nice shirt with clean jeans (none of that distressed crap for me, thanks) and a hot pair of shoes- heels or cute flats- is a fantastic look.

  29. Gravatar Icon

    Meritt
    said,

    October 30, 2007 at 4:06 pm

    Ok you already have like, 23 answers and the last thing you need is yet another opinion… so I’ll just tell you that I am one of those women that absolutely cannot IMAGINE wearing heels with my jeans.

    I thought it looked stupid in the 1980’s when they did it (skinny jeans and high red heels… remember that?) and I can’t do it now.

    I feel like I look stupid and I probably ‘do’ just because it’s not me. I do wear my high tops with jeans… and when I need to be more dressy I wear my black shoes - or even a pair of brown AE shoes with them. But you won’t catch me in jeans and high heels together… ever.

  30. Gravatar Icon

    Audrey
    said,

    October 30, 2007 at 4:07 pm

    I’m with people above: jeans + heels or boots = hott with pretty much any top. It’s a good look. Go for it.

  31. Gravatar Icon

    Laurel
    said,

    October 30, 2007 at 4:13 pm

    Hooray for ballet flats!! I’m glad you found some. If you get an ubercomfy pair, they are perfect for jeans without looking too casual.

  32. Gravatar Icon

    Emily
    said,

    October 30, 2007 at 4:14 pm

    I’m sayin black chucks. They’re cute with t-shirts or a little bit nicer tops.

  33. Gravatar Icon

    kerrianne
    said,

    October 30, 2007 at 4:54 pm

    First of all, you are quite cute.

    Secondly, I would suggest wearing a pair of cute comfy and yet stylish flats with jeans. I live in such attire, and own myriad flats that match various shirts and jeans and some that are even dressy enough to pair with work slacks.

    Plus! their comfy. More comfy than most tennis shoes, in my opinion. : )

  34. Gravatar Icon

    ali
    said,

    October 30, 2007 at 5:54 pm

    i have this problem pretty much every day of my life. my office went from being fancy-ish to being a free-for-all..and i’m pretty much screwed and have nothing to wear. every single day.

  35. Gravatar Icon

    ali
    said,

    October 30, 2007 at 5:54 pm

    but i do wear a lot of jeans, heels, turtlenecks in the winter. and it seems to work.

  36. Gravatar Icon

    daring one
    said,

    October 30, 2007 at 6:55 pm

    Boots, I say.

  37. Gravatar Icon

    Frema
    said,

    October 30, 2007 at 7:20 pm

    First of all, you can totally wear those tops with jeans.

    Second, hooray for ballet flats! Though boots are another great accessory. And I’ve got tons of black shoes with heels that aren’t high heels, and I like to pair those with jeans. But sometimes I’ll just wear a fun top, jeans, and sneakers, too.

  38. Gravatar Icon

    Operation Pink Herring
    said,

    October 30, 2007 at 7:23 pm

    Ok, first off: Don’t ever let me hear you say that Casual Friday sucks again. EVER. Casual Day is all that gets me through the week.

    I see nothing wrong with jeans, sneakers and a cute top. Then again, I’m not the most fashionable person. But both the tops you linked to would be great with jeans, and maybe some shoes like this: http://www.ninewest.com/n/browse/product.s?productId=2872724&source=category&index=2&prodIndex=2&listSize=14&categoryId=

    I have a pair like them (with a plain silver circle instead of the big jewel) and they are super comfy.

    Last but not least: you will not look like an idiot wearing heels and biznass pants at your family gatherings. I am always envious of those people (i’ll be in my jeans and an old navy fleece zip-up shirt), wishing that I had the energy to wear real clothes when it’s not mandatory (at work)

  39. Gravatar Icon

    Jihan
    said,

    October 30, 2007 at 9:40 pm

    To be quite honest: I look a hundred times better in more formal clothes. I need more sophistication to make me look halfway put-together. But once in a while I get crazy and throw on a pair of yoga pants (not that I do yoga or anything) with a sweatshirt and my husband asks “are you sick?”
    With that said, some people look silly and un-natural in formal clothing but in a jean jacket and track pants they look terribly chic.

  40. Gravatar Icon

    Melain
    said,

    October 30, 2007 at 9:59 pm

    You can wear all your tops with some cute little wedges or mules or oxfords or some flat boots, which are all the rage right now… The land of shoes is far too vast to limit yourself to just sneakers and heels!

  41. Gravatar Icon

    Brie
    said,

    October 31, 2007 at 1:35 am

    How about clogs or mules? I wear clogs to work every day (Klogs brand) super comfy…but I’m on my feet all day in a hospital. Those particular ones I paid about $45 for, but Kohl’s is having an awesome sale today. I went there but didn’t find anything I couldn’t live without (at least today).

  42. Gravatar Icon

    metalia
    said,

    October 31, 2007 at 2:03 am

    I was going to say ballet flats and skimmers, but I see I’ve been beaten to the punch, so I’ll mix things up a bit and go with clear 5-inch stripper heels. Just wear them with CONFIDENCE.

  43. Gravatar Icon

    Steph T
    said,

    October 31, 2007 at 3:43 am

    I have these cute Merrill shoes that I got at DSW for $25. They are like a comfortable like a tennis shoe, but they are sleeker and more stylish than the traditional. I’m also a big fan of my Crocs and they have a really cute shoe called Alice that I think would be perfect with jeans.

  44. Gravatar Icon

    Sara
    said,

    October 31, 2007 at 7:10 am

    I love my closed back clogs. I know you don’t have much to spend on shoes, but there are some decent clogs that aren’t Dansko at outlet type places. I love them with jeans and I wear mine with nicer, casual slacks to work (I have a polished black pair). They are great for NW weather. Every fee years, I cough up the money because they last and last and polish up well.

  45. Gravatar Icon

    Christar
    said,

    October 31, 2007 at 6:25 pm

    I always wear jeans, and I just wear converse chucks with them. That’s about it. I wear flare jeans because I like them. I’m not a skinny~jean sort of person.
    Hope you find something to go with your jeans!

  46. Gravatar Icon

    Anth
    said,

    November 1, 2007 at 4:12 am

    Well obviously you have already embraced the ballet flats, which is what I was going to say. Myself, I can’t wear them. I know that under my jeans my legs are looking stumpy (flats on me = badness) so I just can’t bring myself to wear them ever. So I wear sneakers all the time with my jeans.

    From what I can see of your red shirt, it would look totally cute with dark-rinse jeans.

  47. Gravatar Icon

    jamie
    said,

    November 1, 2007 at 6:34 pm

    i was in the same boat this fall when the hubby and i went to a wedding with all of his college buddies. i couldn’t walk around town in high heels or flip-flops and i wasn’t going to wear black a-line skirts or pant suits all weekend. instead, i went to old navy and bought some cute (and cheap!) sweater dresses that went with everything and then bought a pair of flat aerosoles shoes that kind of looked like retro mary janes. unfortunately, i bought them right before the trip and then got blisters because i didn’t break them in before walking for hours through airports and around town. oh well. good luck on your search! and if all else fails, there is nothing wrong with a good pair of yoga pants!

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