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I actually think layering a long sleeved t-shirt under any type of casual type can look very cute! Go for it! All your ideas sound really cute!
Oh, one other comment. One thing that has been mentioned a lot now that leggings are such a trend is that leggings are not 'pants' - I wear them often but under long tunics or dresses only. A rule I read was if the top isn't four inches from the knee or longer, don't wear just leggings.
I'm a big fan of the cheap black and grey legging from target. $6 a pair and they ave a wide, flat elastic band at the top which doesn't seem to give me an imaginary roll like some other leggings or tights do!
Layering totally works. You aren't limited to black or white but those are safe colors.
I buy leggings at Express. They last me a very long time and keep me warm :)
Haha, I just bit the bullet and bought skinny jeans that I swore I would never ever, ever, ever buy or wear too!
I wouldn't wear a long-sleeved shirt with the dresses, but that's just me. I would definitely go for some awesome pairs of tights. Tights come in so many different thicknesses, patterns and colors now!
As for your last, unrelated question...no, you will not be a mess. I'm sure you will be super cute. If all else fails, get some girlfriends over with a bottle of wine and have them help you put some outfits together if you're unsure. Have fun!
@christalynn11: my rule for leggings is it must cover all of my bits and pieces. And I only wear dark colors, so if anything creeps up when I am reaching for something on a high shelf, everything is still covered.
I HATE seeing girls in white leggings wearing them as pants. HATE.
Yup! I just bought TWO pairs of skinny jeans. They looked really cute in the store but when I tried them on for work, it just didn't look right. Maybe I had the wrong pairs of shoes or maybe I need to add a belt or something. But I just couldn't get it to work. Until I figure out a look that works, it will stay in my closet til then. :/
ETA: Oh, as for sweater dresses with leggings. I don't know if it's my thing. I don't like skin tight clothes. For some reason, I'm afraid of people seeing my underwear or seeing the line from my underwear. I am very self conscious about that. But I do see a ton of women who rock that look. You should show some pics.
@christalynn11: I agree that legging are not pants. I know legging is a hot item right now, but I've seen a lot of girl wear legging as pants. Sometimes they're so tight and stretcht to a point I can see the underwear under the legging or leave no imaginary to the crotch area.
One time I had to tell my sister to go change her legging or put on a longer top because I could see her underwear. She didn't believe me until I described how it looks. 
Shew LOL i am learning lol did I mention I am HORRIBLE At this stuff?? I hate shopping bc I get frustrated!
I think black and white is what I am more comfortable with for now LOL except maybe a colored under the black dress.
@christalynn11: LOL no no i totally agree i have seen some ppl that i think hmmm you really need some pants or a a skirt or something on... Almost all of my sweater dresses come around the knee so I think i am good that is the only thing i can ever see me wearing leggings with
I looked at Target, walmart Jc Pennys and Old Navy but Maybe I am looking in the wrong department for leggings... are they with the clothes? are they with the underwear? are they like where the panty hose are?
@waffle: lol My husband talked me into buying them or I probably would not have! I have always hated the look of them with Shoes bc they make ppls feet look really big! I honestly am still not in love with them because I have always perfered a boot cut or flare soemthing to come down over the top of my shoe ... but i will admit I see alot of women in alot of cute outfits with the skinny jeans with the boots over top the jeans... so thats my plan LOL i cant bring myself to venture into wearing them with flats and all yet lol!
I get what your saying about the layering in a way i think it will take away from the look of it but I get cold really easily so for me its more about function than fashion Ya know!
@MissTatas: we dont have an express store in this area LOL i live in a fairly small town...
@FutureMrs.Harless: Ugh same problem with the sweater dresses...they are all short sleeved! (well most of what I have seen anyway...) It is so annoying. I dunno about layering, it really depends on the sweater dress. My rule for leggings is the shirt I am wearing with them has to cover my butt cause I don't wanna look like sausage casings!
@MsJ26: I know i mean i dont get it I even saw some that was almost sleeveless.... to me a sweater dress is definately a late fall or winter look so why not make them more weather appropriate for so and make more of them long sleeve.... I found maybe 2 with long sleeve and they bascially jsut looked like really really long v neck wide striped sweaters and I just felt like they were just wearing me ... wasnt for my body style
@yrret107: I personally think that the skinny jeans look best with a flat like a ballet flat or have them tucked in a boot ... thats just me... I have seen some ppl wear heels with them but i dunno that I like that look myself and wearing them with something like a tennis shoe to me makes the person look like they have on clown shoes.
I love sweater dresses! My favorite is a Diane von Furstenberg cowlneck sweaterdress in charcoal that I bought a few years back. If yours looks anything like mine, I wouldn't layer shirts under it. If the sweaterdress isn't sufficiently warm enough by itself, then top it with a coat. I'm imagining a shirt layer peeking out from under a sweaterdress and it's just looking a little...silly.
I am never a fan of leggings, I'm going to be honest, but I do think they look better or worse with some things. I don't really feel them with sweaterdresses, at least none that I'm imagining (can you post pics of these recent acquisitions? :P). They wouldn't look bad or anything, but I think you should go for some thick opaque tights! Plus they keep your feetsies warm, which leggings do not. Go to your local department store and ask them if the have Hue tights. They're inexpensive and come in a million colors and stay up pretty well, usually. I think that with the teal and purple dresses, grey, charcoal, brown, or classic black tights would look great. For the black one, you can go wild with colors! If you're up for a bit of a splurge that will feel like heaven on your legs, keep you completely separate from the cold atmosphere, will look AWESOME, and won't snag no matter what the heck you do to them, for years--go for Wolfords. Seriously. I love their Velvet de Luxe tights. They cost about $40 and last 10x as long as a cheaper pair, plus they feel so silky and tightly knit, stay up perfectly, and look so amazing. Seriously...I've owned my pairs for as much as five years and pretty much never wear pants, so they get A LOT of use and yet last for ages. I have rubbed them against concrete, had my cat pull at them, snagged them on metals chairs, the works, and yet amazingly, they don't run. I think they're made of magic or something.
Okay, I swear I don't work for Wolford. :P I just wanted to throw that out there. For the price you put down up front, you get returns way greater than you would from 4 pairs of cheaper tights.
And the final outfit you described...no, you will not look a mess! I'm sure you're adorable and that outfit sounds very cold-weather appropriate.
Edit: just saw your sweater dresses are sleeveless. Silly clothing makers! Then I would layer a shirt under that, but make sure the neckline doesn't peak out from the neck of the dress. That sounds like it could look a bit awkward. On the plus side, layering shirts underneath is a fun way to add color to your outfits. :)
They are with the regular juniors clothes at Target...
I think long sleeves underneath would be totally fine in a complementary color or black.
@FutureMrs.Harless: Glad to hear I am not the only one...I was beginning to think I was blind or something...
@veganglam: AHH lol your not helping anything! LOL J/K see im on the legging tights debate right now i just cant seem to find anything that doesnt look like spandex, colored panty hose or that is more on the heavy duty side.
See the top peaking out is what I wondered would ruin the look... hmmm I might just have to play around with it... because While i definately would pair it with a coat probably the black wool pea coat i have ... because winter here is typically around 20-30 degrees i still tend to get cold even when inside and it is not always practical to leave your coat on... like at a restraunt, someones house etc... etc
Oh, I just want to add that I recently I found out they make denim legging to wear with short sweaters w/o fear of exposing too much.
@cutexkitty: haha yeah those what i hear ppl are callling Jeggings.. to me I dont get it... if its going to be denim why not just go for skinny jean? isnt it practically the same thing?
@FutureMrs.Harless: Oh no I don't mean to haha! I'd be stunned if your nearest department store didn't have some basic tights. Also, the internet has endless options, would you be up for some online purchases? http://www.dillards.com/endeca/EndecaStartServlet?N=1633866+2010896 has them in lots of colors and for only $8.75/pair when you buy multiples! And, I've never worn this brand before, but 120 denier tights are the heftiest I've seen, so I'm sure they'd be really warm, and these are quite inexpensive! http://www.mytights.com/us/pamela-mann-120-denier-tights.html
I just can't imagine my life without tights...I have a whole drawer of just tights in a million colors and wear them almost every day! They keep your legs AND feet warm and add color and add polish to an outfit.
Whatever you decide to do, I'm sure you'll look lovely. You don't sound nearly so clueless about all this as you purport to be. :P
@veganglam: lol thanks... I try to look pulled together LOL i really do :P It is just hard sometimes because I am really cheap so i dont like to spend money on things I dont feel I absolutely need and DUE to my really petite frame and shortness and small shoes size it makes my options very limited sometimes. Hehe that is why I always take my husband shopping with me because like yesterday I was only planning to buy 1 sweater dress and tried them on for him to help me decide which looked the best and he said "they all look so good and its a good deal why not get all 3" he just makes me feel much better about spending money on myself
@veganglam: maybe for only a shopping trip :P he will hold /carry your big overstuffed heavy purse for you too
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Some of you may have read my previous post about the distress of my winter wardrobeso i went shopping the other day for shoes and ended up with 3 sweater dresses and a pair of skinny jeans which i said i would never own but i bit the bullet after I bought a pair of cute warm black winter boots.
I have 2 questions about the sweater dresses.....
ALL OF them are short sleeve you would think they would make these things in long sleeves but NO...... 2 of them are Cowl necks 1 is teal one is a blended purple color both of them are belted. The other one is a black and has a almost like turtle neck type that looks like it is unbuttoned and pulled to one side lol i hope that made sense.... My question is.... would it look stupid or ruin the look to wear a long sleeve shirt under them on cold days?If not should i stick or black or white?
My second question is I want to buy a pair or two of maybe leggings to wear under them but ... I have not been sucessful in finding any and what i do find are more like footless opaque pantyhose. Or like spandex materials I want something that is thicker than that something that will help keep me somewhat warm... what should i look for and any reccomendation of where to find them? Or should I go for tights?
Now for an unrelated question while i have you here... for those that read the PP i have a ton of long sleeve solid shirts... most are deep rich colors like dark purples and teals and maroons and greens and blues.... I was thinking i could pair this with my dark jeans my new black and grey boots and maybe throw on a vest over top to change up the look a little bit. What do you think would that be cute or just a mess? I also dunno if a fleece or puffer vest would be better and what color to pull it all together and work well will several items i have in my closet.