I need a new outfit idea?

Question

I normally wear slim fitting jeans and a low cut or close fitting top or sweater to go out, but I am getting bored! I usually avoid skirts and dresses simply because I cannot wear high heels. Can you suggest something new that I can wear flats or low heeled boots with? Also, I live in Chicago so it's starting to get cold... anyone who sends outfit pics will have a higher chance of getting best answer! :)

whitesideddolphin - thanks for your help! well here are some details. I am 31 yrs old, so a couple of the outfits others suggested were too teen-looking for me. I like a minimalist look with a nice fit and bold but few accessories (think Jennifer Aniston as opposed to someone more flashy) and I love neutral or jewel tone colors but would rarely wear pastels. What else can you suggest ? :)

Answer 1

I feel your pain (quite literally) concerning high heels, I can't wear high heels for longer than about half an hour, but thank goodness for kitten heels and slouchy flat boots! I personally love a slightly boho look, so the low heeled, slouchy boots often go very well with that, so absolutely not a reason not to wear skirts! In the summer you can pretty much wear flipflops with most dresses/ skirts but I can see how this would be a problem in the winter.
Here are some sets I made featuring flat(ish) boots with skirt combinations to give you some ideas of what I personally would combine flat boots with:
http://www.polyvore.com/cgi/set?id=285718
http://www.polyvore.com/cgi/set?id=259806
http://www.polyvore.com/cgi/set?id=148806
http://www.polyvore.com/cgi/set?id=150337
http://www.polyvore.com/cgi/set?id=143574
http://www.polyvore.com/cgi/set?id=369424
Not all of them are winter fit, I admit, but with a lot of them some tights/stockings and a coat will probably make them workable. If you are not familiar with this site, it has the advantage that all clothes used in the outfit are listed next to the set so you can check where they are from and if they are still available.
There is also nothing wrong with a jeans and top look, just be a bit more variable, try out different cuts for sweaters, don't go for the same style all the time, look for some detailing, different interesting cuts that make the top look more interesting or go for layers, they allow you more variability, there is only so many different cuts for sweaters but a cami or a blouse under a nice cardigan and a well fitted coat gives you a lot more variability to work with.
If you like you could add some more details about preferred clothing style/shops/colours etc and I could try putting together an outfit for you especially suited to a colder climate.

EDIT: I am a bit busy today, so I have't hd the oppurtunity to come up with anything myself but I did a search on polyvore for some inspiration and came up with a few things, I'll get on putting something together myself this evening.
Sticking with pants but a bit more formal, this may be a bit too fussy with all the acessories but I quite liked the look:
http://www.polyvore.com/cgi/set?id=59509
Instead of the heels, something like:
http://www.target.com/Xhilaration-Sable-Ballerina-Flats-Gold/dp/B000KHTFAO/sr=1-1/qid=1194956316/ref=sr_1_1/602-4815996-1645457?ie=UTF8&index=target&rh=k%3Agold%20flats&page=1
or
http://www.target.com/Mossimo-Dani-Cross-Toe-Flats-Gold/dp/B000PRWL3C/sr=1-2/qid=1194956316/ref=sr_1_2/602-4815996-1645457?ie=UTF8&index=target&rh=k%3Agold%20flats&page=1
and
http://www.bebe.com/gp/product/B000PQ04A0/sr=1-4/qid=1194956427/ref=sr_1_4?ie=UTF8&fontColor=000000&node=235559011&m=A2FMOXN01TSNYY&totalItemIn1Page=24&startIndex=0&displayPageNum=1&bbBrand=core&field-clothing-size=&keywords=&firstPageItemNum=0&title=&restPageHasColor=0&myViewID=embedded&displaySalePrice=0&displayItemNum=12&standardPageSize=12&size=12&rh=n%3A235559011&page=1&bgColor=
That is if the weather is not too slushy outside that is, I can see how it wouldn't work then, but for nice dry yet cold day. maybe.
For more casual, take the cue from Jennifer, layer rather than just wear one top:
http://www.polyvore.com/cgi/set?id=170910
http://www.polyvore.com/cgi/set?id=201388 (substitute with flats from first outfit)
http://www.polyvore.com/cgi/set?id=288683 (again simple cream flats would probably work)
Very simple:
http://www.polyvore.com/cgi/set?id=12289
add a coat:
http://www.bebe.com/gp/product/B000RPF7L0/sr=1-23/qid=1194956427/ref=sr_1_23?ie=UTF8&fontColor=000000&node=235559011&m=A2FMOXN01TSNYY&totalItemIn1Page=24&startIndex=0&displayPageNum=1&bbBrand=core&field-clothing-size=&keywords=&firstPageItemNum=0&title=&restPageHasColor=0&myViewID=embedded&displaySalePrice=0&displayItemNum=12&standardPageSize=12&size=12&rh=n%3A235559011&page=2&bgColor=
Substitute for flatter boots:
http://www.amazon.com/dp/B000VB8F9G/ref=nosim/?tag=nextag-shoes01-20&creative=380333&creativeASIN=B000VB8F9G&linkCode=asn
Add some accessories:
http://www.ae.com/web/browse/product.jsp?catId=cat90054&productId=1429_4022
http://www.forever21.com/product.asp?catalog%5Fname=FOREVER21&category%5Fname=bracelets&product%5Fid=1042281179&Page=6
http://www.forever21.com/product.asp?catalog%5Fname=FOREVER21&category%5Fname=necklaces&product%5Fid=1043294732&Page=1

Edit 2:

I don’t think there is anything fundamentally wrong with the jeans and top look but the key is too make it a bit more interesting by experimenting with different cuts, for example detailing on sleeves, of combining different materials and textures to add some interest through layering and prevent it from being bland, accessories can completely turn around an outfit as well, so pay attention to that.
Casual and neutral black/grey shades outfit:
http://www.bebe.com/gp/product/B000UC7KLU/sr=1-20/qid=1195002770/ref=sr_1_20?ie=UTF8&fontColor=000000&node=15378531&m=A2FMOXN01TSNYY&totalItemIn1Page=&startIndex=8&displayPageNum=2&bbBrand=core&field-clothing-size=&keywords=&firstPageItemNum=8&title=&restPageHasColor=1&myViewID=embedded-leaf&displaySalePrice=0&displayItemNum=16&standardPageSize=16&size=24&rh=n%3A15378531&page=1&bgColor=FFFFFF
Simple black cardi with cute sleeves over simple grey cami:
http://www.abercrombie.com/webapp/wcs/stores/servlet/product_10051_10901_349742_-1_12270_12203
Alternatively, if it is too cold for the cami, a simple long sleeved tee:
http://www.abercrombie.com/webapp/wcs/stores/servlet/product_10051_10901_375125_-1_12274_12203
Jeans, slim or bootcut, your choice, with a belt to give some more interest to the outfit:
http://www.bebe.com/gp/product/B000VT5TEM/sr=1-7/qid=1195003312/ref=sr_1_7?ie=UTF8&fontColor=000000&node=15388091&m=A2FMOXN01TSNYY&totalItemIn1Page=16&startIndex=0&displayPageNum=1&bbBrand=core&field-clothing-size=&keywords=&firstPageItemNum=0&title=&restPageHasColor=0&myViewID=embedded&displaySalePrice=0&displayItemNum=12&standardPageSize=12&size=12&rh=n%3A15388091&page=1&bgColor=
with some flats:
http://www.forever21.com/product.asp?catalog%5Fname=FOREVER21&category%5Fname=shoes&product%5Fid=2042435979&Page=1
or warm boots of some sort.
Bag:
http://www.forever21.com/product.asp?catalog%5Fname=FOREVER21&category%5Fname=handbags&product%5Fid=1038347711&Page=1
and maybe some touches of silver to add further interest:
http://www.forever21.com/product.asp?catalog%5Fname=FOREVER21&category%5Fname=bracelets&product%5Fid=1042718489&Page=3
maybe some earrings or substitute the black bag for a silver one.
Some other sets, I tried to keep in clean cut and functional ( a challenge for me, I love little details…) as well as warm:
http://www.polyvore.com/cgi/set?id=378809
Maybe, try out skirts and dresses, it may be winter but with some nice slouchy boots and some tights (maybe patterned), they re definitely still workable/, maybe try out some sweater dresses (http://www.polyvore.com/cgi/thing?id=312037, http://store.alloy.com/item.do?categoryID=113&itemID=47725&sizeFilter=&colorFilter=&brandFilter= ), whether over jeans or if they are long enough 9or you are cofident enough) just with some boots, a coat and a nice fitted coat.
Some sets I found that you may like going by some of your descriptions, not all necessarily winter safe but maybe it will give you some inspiration;
Mainly neutral:
http://www.polyvore.com/cgi/set?id=149890
http://www.polyvore.com/cgi/set?id=276125
http://www.polyvore.com/cgi/set?id=322636
http://www.polyvore.com/cgi/set?id=376848
http://www.polyvore.com/cgi/set?id=159062
http://www.polyvore.com/cgi/set?id=277191
http://www.polyvore.com/cgi/set?id=51749
http://www.polyvore.com/cgi/set?id=271457
http://www.polyvore.com/cgi/set?id=279559
http://www.polyvore.com/cgi/set?id=319203
http://www.polyvore.com/cgi/set?id=269860
Also thought this look on the Anthropologie side is not a bad one:
http://www.anthropologie.com/anthro/catalog/category.jsp?navAction=jump&navCount=127&id=APPAREL

Answer 2

There is no law that says one has to wear heels with a dress or skirt. If there is, then I've gotten out of several tickets. I don't like the current styles of heels they're too high and unnatural and I think some just look tacky.

A couple of summers ago, I lost too much weight and some of my shorts were too big. I did have two denim skirts that I wore instead. (I didn't want to buy anything as I wanted to gain weight again. I was underweight.) Depending on my mood and where I was going, I would either wear a fitted blouse and loafers with them or a fitted Tshirt and white canvas shoes (fake Keds from Wal-Mart). Earlier this year I helped with my church's clothing drive. While cleaning up one month, I found a khaki skirt. Since it was leftover, I took it. It was nice and big and I belted it with a scarf that I bought at another church rummage sale for only a dime. (I've gotten many compliments on that, too.) Since I didn't want to spend much money on clothes that I was only going to wear a few months, it was great as it lasted me half of my pregnancy. I also wore it in lieu of shorts with a blouse and loafers.

I also have standard "uniform". Bottoms-- jeans, khakis or dress pants with a fitted blouse and maybe a sweater vest but always with a blazer. I also like tight fitting tanks under my blouses for an extra layer without bulk. This winter I'm going to splurge for a nursing tank. (The two i have , a black one and a tan/nude one are a bit small and I have to pull them up to feed my two-month old daughter. However, I have to do the same with the sweater, too.) Some of my blouses are too small over my breasts (I'm three sizes bigger than what I was pre-pregnancy), so buying the one tank will be cheaper. I wear boots in winter that have thick heels so I can actually walk in them. The thing about my outfits is that they are fitting for any occasion-- A "nice" dinner out, or just grocery shopping. (I'm a stay at home mom, so I do more grocery shopping, especially since we can make many meals better and cheaper.) Plus, I stick with classic styles so I don't "have to" go shopping as often and because it's what I like. I've learned that khakis and a shirt with loafers and a blazer work for almost any situation. Can't beat that.

Answer 3

Try wearing things like capris with a little bit of design on them I will sometime cut the bottoms off of a pair of jeans and add a cute design they might work well in summer for you But for fall and winter, I suggest wearing a cute long sleeve tee and a warm winter coat Mossimo Supply Co. Corduroy Peacoat - Ebony and Juniors' Mossimo Supply Co. Long-Sleeve Turtleneck Shirt - Ebony and for bottoms and shoes Juniors' Mossimo Supply Co. Denim Wide-Leg Double Scoop Flap-Pocket Jeans - Light Indigo
And Xhilaration® Flora Stretch Boots - Black

Answer 4

Seriously, you can wear a skirt w/out heels. I've been wearing skirts every day. I've been wearing them every day of my life. You can find a nice jean skirt and put on a nice top with it.

Answer 5

try wearing "flare" jeans with a pair of flats and a baydoll top

jeans: http://www.abercrombie.com/webapp/wcs/stores/servlet/product_10051_10901_290357_-1_12261_12203

shoes:http://www.payless.com/Catalog/ProductDetail.aspx?&TLC=Womens&SLC=WomensCasuals&BLC=WomensPromoCanvas&Width=Regular&ItemCode=58837&LotNumber=058498&Type=Adult&Popularity=368&DescriptiveColor=Brown

or:http://www.payless.com/Catalog/ProductDetail.aspx?&TLC=Womens&SLC=WomensCasuals&BLC=WomensPromoCanvas&Width=Regular&ItemCode=56699&LotNumber=056747&Type=Adult&Popularity=326&DescriptiveColor=Black

Shirt: http://www.ae.com/web/browse/product.jsp?catId=cat90090&productId=1455_7791