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How to Style & Wear a Difficult Piece


I’m sure you all have that piece of clothing that you like very much, but can’t seem to be able to pair with anything. I know I have several, so in this article (and perhaps, future ones, too), I am going to try and find  ways to style and wear “difficult” items: helping you by helping myself!

Below, I’ll be focusing on styling a sweater that I got as a Christmas present two years ago and have probably worn three times since. As you can see, it’s a rather chunky sweater, with a nice pattern on the front and a neutral color which should make things easier. The giant problem I’ve had with it is that it is very short! Even as I try to pull it down, it’s still not as long as I’d be comfortable wearing:

Too-short sweater

(And now my bare stomach is on the internet – awesome.) Anyway, my main concern was finding a way to cover my midsection and also to maintain a balance between the bottom and the chunkier top, so read on to see how I did that.

1. Start with the simplest solution.

For my first outfit, I went with the most obvious choice, and mixed the cropped sweater with some high-waisted pants. Even though I wore some high platform shoes, by rolling up my sleeves and adding a masculine belt, I managed to keep the whole look casual enough to wear to class on a chilly day.

How to style a too-short sweater

The key thing to remember here is this: if the top is too short, compensate with high-waisted bottoms! We learned this from the crop tops trend (see: how to wear a crop top): the easiest way to wear them is with high-waisted shorts, skirts, or pants.

2. Go short and sweet!

A short sweater like this is perfect for layering! Here, I wanted to create a more feminine outfit but couldn’t decide between a dress or a skirt. I chose the latter – because this skirt is the kind that sits high on the waist, instead of resting on the hips, I wasn’t worried that I’d be showing too much skin. Of course, you could opt to wear a dress underneath and no one would be able to tell the difference!

How to style a too-short sweater with a skirt

The reason I chose the chunky sandals is that I needed to wear something to compensate for the “heavy” top – small, delicate shoes wouldn’t have worked. Also, in this combination, the sweater works as outerwear: imagine wearing it on a spring day, ready to take it off once the sun begins to shine. And in case you thought such a sweater couldn’t complement a more delicate piece of jewellery, I believe I managed to somewhat disprove that theory.

3. Wear something underneath.

But don’t wear something that you hope will go unnoticed – be bold! Wear a crazy fuchsia t-shirt! Or maybe a neon green tank top! I chose a striped bodysuit and I unintentionally matched its colors to the scarf I put on. But who cares, as long as I can comfortably lift my arms without showing my stomach.

How to style a short sweater over a bright tee

Also, notice that I didn’t go too crazy with the accessories and in this case, I actually forgot to put on a belt. (But I think the digital replacement will do for the time being.) My favorite thing about this look is that it looks pretty basic if I sit still, but once I start moving, you can see the bright colors peeking from underneath – I love that!

4. If all else fails, cover up!

Of course, with any tough piece, there is always a chance that nothing will seem to work and if that is the case, you need to find a work-around. My idea was to wear a denim jacket on top of everything, with only the sleeves of the sweater being still visible - denim on denim will always look good in my opinion. (Just be sure you don’t match the denim washes – you always want to mis-match in this case!)

Denim on denim

Another alternative might be a faux-fur vest or  – why not? – a blazer. If you’re struggling to fight the cold these days (as I am) no number of layers will seem too high.

Finally, the green boots add a much-needed splash of color to the whole look and all I need to do now is grab a cheerful bag on my way out and the outfit is complete!

Success! Your turn now.

In the end, I’ve come up with four different outfits but, most importantly, I realized that this piece may not be as difficult to wear as I initially thought. I want to hear from you now: opinions, suggestions? What’s your “impossible” piece? Leave a comment and maybe I’ll write a post about it.

Posted on on March 1, 2013 / Filed Under: Fashion Tips / Tags: , , ,

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27 Responses to “How to Style & Wear a Difficult Piece”

  1. 1
    March 1st, 2013 at 5:04 pm

    Wearing cropped sweaters is actually one of my favourite things in the winter. I would just wear a tank top underneath and go from there, or I would wear a tunic underneath and then wearing tights and shorts with it.

  2. 2
    March 1st, 2013 at 5:08 pm

    This is my favorite column on CF right now….love this post!

  3. 3
    March 1st, 2013 at 5:36 pm

    I think there are some great ideas here, but they’re poorly executed. All the pants the author wears are SUPER low rise (like…I feel like some girls would need to shave, if you catch my drift – the remind me of those micro-rise jeans that were popular in the late ’90s, early ’00s). Even the “high rise” example is a normal rise pant.

    I don’t think the clunky sandals really work, either. Something lighter in color would be less visually jarring – my mom once told me that shoes should never be darker than your hemline, and while I think most fashion “rules” (ie, no white after Labor Day) are silly, that’s a good rule to follow.

    For the “wear something underneath” tip – I think the look here is good…maybe just not my style. A long tank or tee with leggings, or even a top with a ruffle bottom would be ADORABLE, and would be a good substitute for the peplum trend that’s hot.

  4. 4
    March 1st, 2013 at 6:15 pm

    You have IMPECCABLE style. seriously! love your posts! :)

  5. 5
    March 1st, 2013 at 6:18 pm

    I really like some of your ideas
    The sweater looks amazing
    I love the 1st and 4th look
    The second is quite nice too….But I would substitute the heels with flats

  6. 6
    March 1st, 2013 at 7:48 pm

    love this post!!

  7. 7
    March 1st, 2013 at 8:06 pm

    Though this is all good advice, why not try and embrace the crop top and wear it as is? Who knows maybe it’ll look really nice with jeans just the way it is!

  8. 8
    March 1st, 2013 at 8:25 pm

    I love your creative posts!! Personally, I would have layered an untucked button-down beneath the sweater to cover my midriff and make it a little more preppy.

    Keep up the great work!

  9. 9
    March 1st, 2013 at 8:55 pm

    I was very excited about reading this post, but have to say that I was a little disappointed. To me, every outfit seems just a bit off. I agree with others about the sandals not being the best choice. Quite honestly, I think you look your best in the top picture where you are pulling your sweater down. The sweater is meant to be cropped and show a little skin.

    Another thing I wanted to point out is the negativity about your body in your article. I have been told off before about complaining about my body when I am perfectly normal, so I know it’s hard to snap out of, but it’s not healthy. You are very thin, and I wouldn’t be surprised if you offended a few girls by stating you’re embarrassed by your stomach. Let’s try to put out positive attitudes about our bodies! :)

    I was hesitant about this trend to, but decided to just go all out. I wear a cropped turtleneck with a highwasted hi-low skirt. It shows about an inch and a half of my stomach, and let me tell you, I get TONS of compliments! The trick to anything cropped is confidence. Something that looks good on everyone.

  10. 10
    March 1st, 2013 at 9:08 pm

    I love this column! It gives me lots of ideas to refresh my wardrobe and my style!

    Btw, Ashley: your mum has given you a bad piece of advice, although it is currently outdated, it has always being said: never wear shoes LIGHTER than your hemline. Just for you to know, as in many cases this rule comes in handy when finding the perfect pair of shoes!!

  11. 11
    March 1st, 2013 at 9:30 pm

    Love these posts!! Actually helpful!!

  12. 12
    March 1st, 2013 at 11:09 pm

    Love it! Speaking of difficult pieces, I actually have a few tighter, long sleeved shirts/sweaters that are a strange length (not quite cropped, not quite hip length) I think I’ve got one pair of wide leg jeans but they’re the same color as one of the shirts and it gives off a style I’m not a big fan of– anyone have any ideas on how to style these?

  13. 13
    March 2nd, 2013 at 12:15 am

    My impossible piece is a bright orange sweater my mom got me for Christmas. So far, i’ve worn it in exactly one way — with jeggings and a white scarf.

  14. 14
    March 2nd, 2013 at 8:39 am

    Just wanna say I really love this column; it’s always handy to see how the outfit looks on someone. I love the first and second looks best, especially the skirt. :D My difficult piece is a really structured pinafore dress that I’ve had for… hell, about a year? I can sort of figure how to do it for winter, but I can’t help thinking it looks odd with sandals or ballet flats.

  15. 15
    March 2nd, 2013 at 1:15 pm

    Wow, I think the people commenting about how you are negative about your body need to chill out. Not everyone feels comfortable showing skin, doesn’t matter if they are skinny or not. I personally like your style. Keep it up

  16. 16
    March 2nd, 2013 at 1:40 pm

    The sweater she has is from H&M, I have the same one too!

    Great post! I have been wearing a t-shirt under mine.

  17. 17
    March 2nd, 2013 at 3:46 pm

    my favorite way to wear cropped sweaters is with a dress, as a skirt. That’s often to hard to pull off with a longer shirt as it tends to make the “skirt” part awkwardly small, but with a cropped sweater it usually works out perfectly.

  18. 18
    March 2nd, 2013 at 4:21 pm

    Love it, but I’ve never been a fan of the “Canadian tuxedo” denim-on-denim look.

  19. 19
    March 3rd, 2013 at 1:34 am

    I agree that the author’s jeans are REALLY low rise. I can only assume that they’re the kind that have a slanted waistband that’s much higher in the back and slung low in the front (I have some like that), otherwise she’d be worrying about more than her midriff sticking out!

    Thinking back to a recent article about styling workout wear, have you tried wearing a pair of yoga pants under your jeans? In my experience, they are usually closer to the natural waist, and if it’s really cold outside they work like stylish long johns. Especially if you have some in a fun color, it could be cute.

  20. 20
    March 3rd, 2013 at 6:46 am

    Thank you all for your comments and especially for your suggestions! (I really liked Ashley’s idea – wearing a ruffled top underneath- nice tip!)
    Now, to those who mentioned I should the sweater as it is and to Gwenivere, who commented on my body image negativity: that is not at all what this is about and I am sorry it looked like it. I don’t feel comfortable showing skin but to me, that’s just a matter of decency. That is the only reason why I wouldn’t wear the sweater like that and I tried to cover myself a bit.
    Erin: I usually wear colored tights underneath my jeans, so it’s kind of the same thing. Also, if it’s cold, I always wear a tank top as the base layer – I really can’t stand the cold haha.

  21. 21
    March 3rd, 2013 at 9:00 am

    Pleaseee! Could you do a post about a red highlow skirt? It was also a present and i really really like it but i just dont know how to wear it!!

  22. 22
    March 3rd, 2013 at 1:27 pm

    Awesome postt..! :)

  23. 23
    March 3rd, 2013 at 3:18 pm

    Thanks for this post, it’s perfect timing because I just got a sweater that’s short and I don’t like showing too much skin either.

  24. 24
    March 3rd, 2013 at 9:17 pm

    Love this post!

  25. 25
    March 4th, 2013 at 6:42 pm

    Great ideas! There’s been a sudden cold snap in Georgia, and I’ve been freezing! I will definately be using these ideas to layer up!

  26. 26
    March 5th, 2013 at 3:22 pm

    I was super excited about this post but all these outfits missed the mark for me. The skirt outfit especially seemed way off base. The skirt, the shoes, just none of it worked. It did come across a little body negative tbh. Also can you maybe take your pictures in better light? It was hard to pick up on details.

  27. 27
    March 7th, 2013 at 2:13 am

    high-low tank dress for winter please?? it seems impossible to style, especially for a shorty like me

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