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Take the Bombshell Out of a Pencil Skirt

Pencil skirts have been the skirt silhouette for many seasons. They are a versatile classic and often very form fitting. 

Form fitting silhouettes have their structured advantages. Their tailored integrity is attractive and achieves a polished appearance. Match a curve hugging pencil skirt with a form fitting top and high heels and you’re on your way to bombshell status. This is an undeniably alluring combination. And one that works every season. 

On the other hand, looking like a bombshell may not be your style aspiration. If this is the case, you’ll want to take some of the bombshell-factor out of a pencil skirt. Matching the slim silhouette with an untucked roomy top is one way of reducing the body conscious effect. As seen in these photos, the tops can be long or cropped, soft or rigid. Some tops are more voluminous than others. Some tops are more dressy than others. You’ll probably find that soft boxy tops are more flattering because of their ability to drape against the body. Boxy poncho type tops work well with pencil skirts too. 

When I suggest the pairing of an untucked roomy top with a pencil skirt, some of my clients are very receptive, while others have their reservations. Understandably, the curvier and fuller busted ladies are less inclined to wear boxy tops because it’s makes them feel larger than they are. Interestingly, it’s also often the curvier ladies who felt “too bombshell” matching a form fitting top with a pencil skirt in the first place. But never fear. We find other clothing silhouettes and outfit combinations to tone down the bombshell-factor, and that’s a topic for another day. 

How do you feel about matching roomy tops with pencil skirts?

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Take the Bombshell Out of a Pencil Skirt

Well, nothing wrong with bombshell! :)

Of these I like the polka dot skirt and striped shirt outfits the best…the rest are just meh. But I’m a total fan of the tucked blouse and pencil skirt classic bombshell look!

Love it! It’s a nice option to have for a classic pencil. A boxy top or soft untucked one create appealing silhouettes that I quite like.

I do it myself, and quite regularly. Tucking in is not the most flattering approach on my body since I have a short and curvy torso. A longer and flowier layer on top makes me feel less like Marilyn and more like me.

I adore this look and aim to buy a navy/ink pencil skirt for this very reason.

I too think it’s a lovely look! Since I’m a bit conscious about my hips, I won’t wear a fitted skirt with a fitted top; if this shall be flattering, the skirt has to fall straight down from my widest point or flare out a little, I think.

I’m really torn. I like some but others look a bit frumpy to me. So, I guess I like it in theory (especially the white sweater/blue skirt combo) but like everything, it depends on the specific combination.

I really love this easy look. Bombshell is so NOT my style, so it’s great to see some less vavavoom options for pencil skirts. Like lemonade said, this look would make me feel less like Marilyn and more like me. In fact, I do wear looks like this often when the weather gets warm.

My only concern is proportion and length. I still have some questions about wearing loose untucked tops with pencil skirts and what looks best. Maybe another post to help us style this look, Angie? :)

This is the *only* way I wear my pencils. I’m not comfortable with bombshell for day, so I choose a nice slouchy knit like the Alexander Wang you’ve shown. Great looks!

I love this look, I think it looks really good if the top is made from a soft material contrasting to the skirt material.

Big thumbs up from me. Voluminous or boxy top + pencil skirt always feels refreshing to me. I love the playful element it brings to the silhouette too

I adore this silhouette, and I love seeing the examples you’ve given. Since I never wear high heels, and my style is about as far from bombshell as you can get, I am always looking for ways to “de-bombshell” my pencil skirts, of which I have 4. I’ve been getting a lot of mileage out of pairing my frenchi NAS poncho-sweater with my pencil skirt, and these photos give me some more ideas. Thanks!

As a pear whose lower body shape makes all fitted skirts bombshelly whether I want it or not, I like this look. Assuming I can find a true pencil that fits me, I’d definitely try it.

I have this problem, that I don’t need to be so dressy that a pencil represents But a roomy shirt just makes me feel frumpy and leaves me waistless.

I might be inspired by the sweater options to try a heavy knit over a pencil.

I saw two celeb photos recently where they wore the skirt with strappy tops. I saved them both hoping to find a suitable top this summer to try this with. Only issue there…age appropriate?

While I love wearing my pencil skirts with tucekd tops in attempt to bring a little bombshell to the business world, there are times where I feel extremely self conscious about the look. For example, on days where I am meeting with our board members (the majority of which are 65 or older males) I would wear my pencil skirt because I felt that I wouldn’t be taken seriously. The thought of pairing my pencil skirt with a boxy top intrigues me and would allow me to be true to my style while toning it down a bit for the board members.

I also think this idea is a great way to transition the pencil skirt from the office to more casual settings. Thanks for posting this Angie!

I do this often. I love the juxtaposition of proportions, the reverse of wearing a fitted top and wide legs or full skirt. I prefer the top to be a bit shorter. I think this works especially well on rectangular body types. An hourglass or pear shape may need more waist definition, depending on the length of the top. I also think the longer length pencil skirt adds more to the dramatic proportions.

Love this take on the pencil skirt. I’ve stayed away from them in the past, but maybe I should give one a try.

I wear pencil skirts frequently, usually with a longer, softer layer on top. Just picked up a denim shirt (fitted, not tight) that I’m dying to try with several of my pencil skirts. For years I shied away from pencil skirts, thinking they wouldn’t work with my curves, but they’re actually the most flattering skirt silhouette for me.

To me, a pencil skirt is made for tucking. Not a fan of the untucked style. To be fair, I don’t have to deal with curves, so I probably lack the sensitivity to being overly bombshell-y.

I think bombshell, done well and with class, is a timeless, killer look.

I really like the mix of roomy top and form fitting skirt. I like this combination just as much when it is skinny jeans and roomy top. I do wish other skirt styles were more abundant in stores though, I find a pencil skirt the hardest style to fit on my pear shape yet it is always the most common choice in stores.

I love the mix of a looser top with a fitted pencil skirt. Not only does it make it less body conscious, it takes down the dressiness factor a notch or two.
I especially love the first combination where the skirt is midi length. Very fun and fashion forward looking.

This is a look that I wear and I love having the option of changing up the silhouette like this. Pencil skirts are my favorite style skirt and I appreciate that they can be so classic and so versatile. I had a couple of cropped boxy sweaters from the early 2000′s that I was considering culling from my closet because I felt that they hit at the largest area of my hips (figure 8 shape hourglass) but the upper left photo gave me the idea of layering these sweaters over a longer untucked colored shell or blouse to counter this effect. Once again, thanks Angie for great, useful inspiration here.

I like this look, even though a “bombshell” look is totally fab, sometimes you just don’t want to give off that vibe and this is a great formula to use and still show your style!

Love this! Choose soft fabric in boxy shape for no overwhelm. Steph

I love this look and I think if I could find the right top, I’d be willing to give it a go!

I also love it! Some of these outfits are amazing!!

You make great points, ladies.

Kyle, I am not curvy or full busted either and often tuck a shirt or blouse into a pencil skirt. My shirts and blouses aren’t that form fitting to start off with though. They blousson around the torso. The top fit definitely “de-bombshell’s” the look. On the other hand, I also wear very formfitting tops un-tucked over my pencil skirts. That combination feels more bombshell to my eye, especially when I wear a higher heel.

Queen Mum, taking the bombshell out of the pencil skirt dresses down the look for sure.

Lisa, I also hope that this is the season for the non-pencil skirt! I love pencil skirts, but enjoy flared skirts too.

Sarah, wearing your poncho with a pencil skirt is precisely the pairing I was referring too :)

I like this look. I’m with Jean in thinking that it tends to work a bit better on rectangles than on some of the other body types, and probably works best of all on tall rectangles (at least in some of its iterations).

I love the loose gold blouse tied at the front – gorgeous! Volume-over-tight is definitely a favourite silhouette for me! :)

I actually prefer the look of a roomier top with the form fitting pencil skirt. It seems more current, casual and fun. As Greenglove, I like the juxtaposition. Of course, my lifestyle is completely casual so that explains part of the attraction. I’m also not the “bombshell” type. A form fitted top tucked would only serve to make me more self conscious of my larger upper body (broad shoulders and larger bust).

Yes! Love the boxy top over the pencil skirt! And the more contrast, the better, so the first photo above is my fave!

Just bought two pencil skirts-one rigid, the other soft and drapey.

You’ve given us some great ideas for pairing a rigid skirt with softer tops. I’m 63 years old and the bombshell look just wouldn’t work (although I don’t think it was ever my style anyway).

After I tried on the drapey skirt, it’s obvious that more structured tops (such as a crisp, no-iron shirt) work best.

I’d love to see some tops pairied with soft skirts.

I prefer a more fitted look with pencil skirts (I tend to tuck to further accentuate my waist) BUT I do have one exception to this rule – I have a pleather mini skirt, very body con pencil sillhouette and I wear it with a longer more drapy top to balance out the bombshell combination of the faux leather, short length, and very body con fit.

Adding to my comment – Angie, my figure is similar to yours. I am an hourglass, but a slim hourglass (not busty, balanced shoulders and hips, defined waist), so that might be why I’m not self-conscious about the potential “bombshell” look of a pencil skirt. I don’t really have a bombshell-type figure, even though I definitely have curves.

Lovely post! My favorite kind of skirts! Always so flattering!

I’m with Goldenpig in finding only the dot skirt and the striped sleeve top outfits attractive out of these. I dare say I LOVE both outfits, which is sort of shocking for this non pencil skirt wearing gal! I might try this out, had I not sold the one pencil I own just yesterday lol.

I love the look on these models. I don’t think I could pull that off though. The combination of a larger bust and short-waistedness makes those tops hang off me in an unflattering way.

These photos are great. I wonder if the look works on curvy women? I try not to wear loose tops as I am hourglass-pear and non-fitted tops can just make me look big. On the other hand, bombshell does not feel appropriate either in my roles as a professional or a mom. I will try, thanks for laying out the principles so nicely.

I do love the bomb shell look, but the polka dot skirt combo, and the grey stripes with black eyelet tunic top combo look pretty terrific to my eye. In the latter I particularly like the contrast between drapey top and form fitting bottom.

Like Angie, I never feel particularly bomb shell-y in a pencil even when I tuck due to my body type. But that’s okay too! I still like the look a lot. ;)

I gave only worn a fitted button down untucked to dress down the look in the summer but a boxy top is not something that ever occurred to me !! Thanks angie for the inspiration as always !!!

Interesting! I have been planning outfits to pack for an upcoming conference and two outfits revolve around a black pencil skirt. One is with a form fitting cardigan, buttoned all the way up and the other is with a loose black cashmere sweater. I wasn’t sure if the loose sweater was ok with the pencil skirt, but now this post has given me the green light! With a very thin, rectangular frame and no curves though, bombshell is a country I have never been sadly. For occasions that require a bit of bombshell, I always have much better results flaunting my back than my front.

Ah, these looks are so awesome and inspiring! I have worn some similar looks but can’t wait to try them. Love this post!

Er, try them ALL.

I tried this just the other day with my urban warrior poncho, and I really liked it! But I still like pencils with fitted tops, too.

I own mostly pencil skirts because I like things that are fitted. However, I don’t like them tight and so it is a bit tricky to get it right. I really appreciate this post, it helps to see visuals. I do not strive for bombshell at all, most of my skirt outfits are worn to church or church related events. I absolutelylove the look of the red leather skirt on the bottom left, I don’t know if I would wear it but it sure speaks to me!

This is exactly why I find pencil skirts harder to style – I just don’t have a sinhgle bombshell bone in my body! Angie, as usual you were able to articulate what I could not – thank you. Now I have a new inspiration to play with my wo pencil skirts!
I LOVE almost all of these examples (except the bottom left) but i am especially smitten with a polka dot skirt.

I really like this silhouette, it looks interesting. But I’m not sure it likes me back – I’m always hesitating with boxy tops because I feel like I look instantly much bigger than I am.

I love the Alexander Wang and DvF looks in the second row (if the skirts were a tad longer) and while I don’t get my two pencil skirts out very often (black and yellow), this de-bombshelled version feels very good for my dressed-up-but-casual style and preferences. An outing to LACMA is planned and this may be what I’ll be wearing!!

Wow! I was just looking for a post like this last week. I’ve changed my style to be more casual, and I was wondering how to keep a pencil skirt from being too formal. Thanks for the great examples!

I’m not sure how I feel about boxy tops and pencil skirts. I’m just working on trying the skirt. I have my first pencil skirt in a long time. I haven’t given it a whirl yet. But I like the idea; the traditional silk blouse always seems so arduous to me to wear.

I like it. In fact, I happen to wear such a combination today. I’ll post it on the forum. :)

I love this idea and love the looks you’ve shown, but none of the models have hips! I feel like I need to be mindful when I do this that I don’t wear voluminous where I go in and tight where I go out (if that makes sense).

I really like this look and it’s a nice change from tucking into pencil skirts.

This is something that I struggle with, so definite food for thought. Because pencil skirts are so body conscious I never wear them to work. I wonder if I could try to find a way that’s not to bombshell and not too dressy. I really like the outfit with the bright blue skirt.

Good discussion. I would agree as a heavier on the top body type the loose top adds to much weight. Although I do find it hard to style a pencil skirt without looking like a bombshell. I love the striped t-shirt.

Frankly, I have only one pencil skirt, black, hanging in my closet that has not been worn since a friend’s wedding last year. (I wore it with tights that were very heavily lacy so that my legs didn’t look like total toothpicks.) Every time I wear something that exposes my skinny legs, people comment or stare, and this leaves me feeling depressed indeed. So I guess I need courage to carry off any type of thing that leaves my legs exposed!

This combination should work pretty well on my rectangular figure is the top is short enough not to turn me into a box. I’m looking forward to finding the right top for this look. I love the first photo with the polkadot pencil skirt.

This pencil skirt lover enjoys them in all combinations!

For myself, I have to admit that I like a little bit of bombshell flair, and I often wear a fitted top with them (though I skip the high heels, and instead choose boots in fall/winter and low to mid heeled pumps or sandals in spring/summer. I think that goes a long way in toning down the bombshell factor). I also love the look of a tucked-in button down shirt. That’s because I consider my waist, hips and butt my “better” features and find that the pencil skirt is the perfect vehicle to accentuate them. That said, I love the look of a cropped boxy top with a pencil skirt, like in the first picture above. Soo cool. I tend not to look it that much on myself – I just hate giving up the waist definition and worry more about belly bulge with that kind of top and stuff – but I might just be too uptight about it. If I found the right top (slightly boxy but not too much so) I’d do it.

All the combos you show look good to me, thanks for giving us more ideas!

I just did this today! I wore my black pencil skirt with a black elbow length tee and a khaki sleeveless roomy cowl neck sweater. I almost took a picture for a WIW, and now I wish I would have! My body reads SO bombshell that it’s helpful to have options to tone it down for times I don’t feel that’s appropriate.

The tucked in version is easier for me to pull off with my body type, but I have managed to look stylish rather than sloppy in a looser top on a few occasions. These days I find that I’m less willing to surrender my waist than I used to be.

I am definitely on board with a looser button down (thinking in particular of my Equipment blouses which run very big) tucked into a pencil skirt but otherwise these looks aren’t resonating for me. They feel a little too fashion forward/edgy for my aesthetic and lifestyle. I can see them on a blog (like Atlantic Pacific’s, in particular) but would never translate this into my own look.

The ONE exception would be that I might try pairing a voluminous, soft sweater with my black leather pencil skirt, but more to counter the harsh/extreme effect of the leather skirt. My regular pencil skirts have never struck me as overly bombshell (and, like Kyle, I don’t have real curves that need to be downplayed).

OK, I really like the first outfit (though not for me, too busty) and the one with the lacy black sweater. The rest, no. Meh. They just emphasize what to me is the essential boringness of a pencil skirt. Also, I guess I just don’t get why you would WANT to wear such a confining article of clothing if you were so averse to a body-conscious look. I mean, why not at least get the benefit of wearing something comfortable, then?

I particularly don’t understand the outfit with the gorgeous black-and-white bag. From the waist down, she is all dolled up. From the waist up, she appears to have rolled out of bed and thrown on a man’s shirt. Where would you wear this? Why?

Call me cranky.

I love pencil skirts – almost the only type of skirt I wear. I don’t like roomy tops. I am bustier. So I instead wear tailored jackets on top of my tops – this helps hide some of the outlines that are more obvious with just the top. And I find that looks sufficieintly professional. I also keep my look fairly polished when wearing pencil skirts – patterned tights, fancier shoes.

I have never given this combination any consideration and now I want to try it! Thanks for the lesson and examples.

I never really was a fan of very wide skirts to begin with, so I frequently wear pencil or a-line skirts that aren’t very wide. That said, I tend to wear them as dresses, because I do love the “bombshell” silhouette (It gives my rectangular shape a bit of VA VA VOOM!).

I did try the loose/drapey top over the pencil skirt though, and I must say that it really depends on the length of the top and your body type. I find that when drapey tops aren’t too wide in the hem, they work best when hitting the hip bone. Looks fantastic on smaller-busted girls though. I tried this look (I’m large busted) and it made me look very boxy and shapeless.

Count me in! I love my pencil skirts and am always looking for different ways to wear them.

the boxy top over a pencil skirt remind me of an alternative 60′s silhouette. post new look pre mary quant.

I love this look and am pretty sure I have seen our lovely Jonesy rocking it. I ventured into this look last winter and am planning on working on it further this Autumn / Winter. Oh and I am large busted but I think if you get the proportions just right it can work.

I find it odd that just when I most need to add a button-down shirt to a pencil skirt and tuck it in (business-like settings) is when it feels most body-conscious! I’m careful with that look for precisely this reason, and usually add at least a softer or quirkier jacket or a scarf to soften the look.

But for preference I usually go with a more business casual look of an untucked looser top or at most a fitted untucked sweater, as shown here. I think it’s interesting that even a regular shirt can look less ‘bombshell’ untucked — as shown in one of the photos. I agree for a full bust the more unstructured tops can be a bit of a widening challenge — but I find even adding a belt on top of an untucked blouse is better than tucking it in, in terms of bombshell or bust-showcasing effect. I like banded tops, peplums and waisted sweaters with more volume up top for precisely this reason.

I also tried my cape-style (but with sleeves) sweater with my tweed pencil skirt this winter and loved that look too.

Thank you for the great visuals, Angie! I tried a loose, boxy tee with a striped pencil skirt last summer and it felt just right to me. I’m looking forward to getting into my closet and trying some new combinations with some of my other skirts.

Very late here, but I had to chime in: I LOVE this combination! I think it can look fab on any body type…I think if the boxy top is nicely fitted through the shoulders and sleeves, it can look just as polished and “figure flattering” as a more streamlined, tucked top, if that makes sense. Deborah, thanks for the shout-out! I do wear this combo a lot :) .

This morning I was running late, and short on ironed work clothes, and as I stared at my wardrobe thinking about the meeting and teaching that I needed to look like a grown-up for, I remembered this post…

Result -black tweed, high waisted, pencil skirt and short purple loose, boxy tee shirt, purple tights and heels. I looked in the mirror and felt stylish, grown-up and myself – perfect.

Thank you for the inspiration (and I wish I’d taken a picture!)

Yesss I LOVE this!! This is the only way I have found to wear my pencil skirt casually that fits my style (wore it just last week for my adjacent colors week in fact!). I haven’t paired with a truly short boxy top, just slouchier tops, and love the idea of boxy pairings going into spring. For me it’s not about removing the bombshell aspect though, with these outfits I’m just trying to dress down the skirt. I don’t have a lot of bombshell in my style, but I also have no problem sporting it. For example, I would be equally comfortable wearing a loose/slouchy top (dressy or casual fabrication) untucked as I would a slim tee (or any casual fabrication) tucked. As an hourglass who wants to wear this style, one would need to be comfortable with waist surrender.

I think it works on tall figure, but not for most types. Just not a big fan of boxy shapeless shirts on women.

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