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I just can't do it. I'm trying!


Night Elf
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I'm 49 so middle age. I love big shirts, sweatshirts, sweaters and tunics to go past my fanny. I wear jeans with them. But I want to wear leggings with a cute pair of boots and look fashionable. I bought two sizes online. One is a very snug fit and I have a feeling this is supposed to be how they're worn. There were no wrinkles at the fanny or knees. The size up felt so much better but wrinkled at the fanny and the knees and poked out on the side of the hips. I'm sure this is not the way to wear leggings. So do I go for the snug fit just for the certain look, or do I continue with jeans and comfort?

 

Also, I only own a pair of suede ankle boots. I wear them with my skirts. They're cute as can be, but I'm not sure they'd look good with these leggings and big shirts. I feel they look sort of formal whereas what I'm seeing girls/ladies wearing are leather boots like combat boots. The leggings are too short for me to wear with a shoe that doesn't cover them up, so it has to be a boot, but do I really want to go out and spend more money on a pair of boots for this one look I'd like to achieve? I suppose if I can get used to the leggings I'd buy more of them and wear them a lot.

 

Right now I'm wearing my big shirts with jeans and my black lace-up vans which my chiropractor called my skater shoes. I love them! They look so good with my jeans. But is it okay to wear such big shirts with just jeans and regular shoes? I don't want to look like a bum but this is how I"ve been dressing for years. It started when I was at my heaviest in 2011 and was trying to hide my body shape. Now I have a nice figure but I still don't care for clothes that fit too tight.

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I think you need to invest in some leggings that 'skim' if you want that look.  That way they won't be wrinkled but they won't be tight and uncomfortable either.  I've had pretty good success with Zella in that regard.  They don't show every underwear seam but they don't bag either. 

 

But if you're more comfy in jeans, consider a pair of jeggings.  Those have the sleek legging look without the OTT huggy tightness.  And you can find them long enough to wear with flats, sandals, OR ankle boots.

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You can get a pair of the taller boots at Walmart for less than $30. I'd go for it to figure it out before investing in a pair of nicer boots. Also, you probably know this but for the tigher fitting pants, wear a shirt or tunic that is like mid thigh length. I think you'll be more comfortable that way. 

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You can get a pair of the taller boots at Walmart for less than $30. I'd go for it to figure it out before investing in a pair of nicer boots. Also, you probably know this but for the tigher fitting pants, wear a shirt or tunic that is like mid thigh length. I think you'll be more comfortable that way. 

 

I've got at least a half dozen shirts that are that long. This is my favorite look. I've just been wearing them with jeans. I'm worried that the oversized shirts with jeans makes me look like I'm dressing out of a rag bag rather than going for some fashion statement.

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I think you need to invest in some leggings that 'skim' if you want that look.  That way they won't be wrinkled but they won't be tight and uncomfortable either.  I've had pretty good success with Zella in that regard.  They don't show every underwear seam but they don't bag either. 

 

But if you're more comfy in jeans, consider a pair of jeggings.  Those have the sleek legging look without the OTT huggy tightness.  And you can find them long enough to wear with flats, sandals, OR ankle boots.

 

What I bought was Apt. 9 tummy control super stretch from Kohls. I'm looking at the Zella leggings on Amazon and they seem the same way, even having tummy control.

 

I thought jeggings fit like leggings but were made out of soft stretch denim.

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Is the shirt oversized in all dimensions, or just long?  If it looks about as fitted as a garbage bag, it may not be a good look.  But I think an unfitted T over jeans is fine, especially if the jeans have a slim line- skinny, straight leg, etc.  

 

I wear nothing but jeans and Ts 99% of the time.  My favorite Ts are the target graphic Ts with the slightly longer in back hemline.  

 

Maybe find a store that has everything you need- shoe department, clothes, etc, and put together the entire leggings/tunic/boot thing in the dressing room and see how you feel.  This is a look I wanted to love as well, but reality is, I'm going to reach for my jeans.  It does keep my dresser uncluttered at least!  

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Is the shirt oversized in all dimensions, or just long?  If it looks about as fitted as a garbage bag, it may not be a good look.  But I think an unfitted T over jeans is fine, especially if the jeans have a slim line- skinny, straight leg, etc.  

 

I wear nothing but jeans and Ts 99% of the time.  My favorite Ts are the target graphic Ts with the slightly longer in back hemline.  

 

Maybe find a store that has everything you need- shoe department, clothes, etc, and put together the entire leggings/tunic/boot thing in the dressing room and see how you feel.  This is a look I wanted to love as well, but reality is, I'm going to reach for my jeans.  It does keep my dresser uncluttered at least!  

 

Some of my shirts are men's large size so they're really big in all dimensions. But I've grown used to wearing men's clothing because they fit me the way I like. Now I can find women's clothes in a long length that isn't as bulky and that's what I've been getting from Trunk Club. They look feminine so I think they're oversized look looks nice. My jeans aren't tight but with the long shirts you can't see that they are loose on my fanny. I did try the next size down but they were too tight for my comfort.

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I've got at least a half dozen shirts that are that long. This is my favorite look. I've just been wearing them with jeans. I'm worried that the oversized shirts with jeans makes me look like I'm dressing out of a rag bag rather than going for some fashion statement.

 

If that's how you like to dress, dress that way. Make sure they are nice shirts and bling yourself up a little. Well placed accessories can make all the difference. :)

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The general rule for fashion is only go for big and loose in one part. If the top is extra big and loose you go for an extra fitted bottom.

 

If the top is plunging the skirt is long. If the skirt is short the neckline should be a bit higher. If you have a flowy skirt wear a more fitted top.

 

With this big flowy shirts they look good with skinny jeans but not traditional utility or bootcut.

 

That said I'm more of a wear what I feel like person. I notice what's in fashion but mostly ignore it...

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I thought you wanted boots that were higher.  Personally I like that look of flowy on top, slim bottoms with boots that come up just under the knee.  

 

No, I was wondering if I should get a different type of boot from the black suede I own. I feel like suede is a formal material and I don't know if my big black sweatshirt and jeans would look right with the suede.

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I was worried that your thread title referred to your new volunteer work. I was relieved to see it was a clothing style problem. I can't reply to that, as I am essentially style-free.

 

No, that's going okay. I've decided cleaning in the mornings is not my favorite thing but it's the one thing that makes me feel most constructive and that what I'm doing is making a difference. I do that only twice a week and go in and socialize with the cats two afternoons a week.

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Most of the time I see the leggings paired with mid calf boots or higher. My daughter wears that style almost exclusively -- leggings and uggs -- she has a cardigan grey style pair that are really cute and a black pair with buckles that she loves.  She usually gets them for a xmas or birthday present though -- It's hard to go out and just buy a pair without guilt. :-) 

 

I have been buying target black leggings -- the champion brand I think it is.Some have tummy control and some don't. They have a lot of different choices. But overall, yes, they are supposed to be smooth -- no wrinkling. 

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