Flats with a pencil skirt?
September 26, 2011 10:12 AM   Subscribe

Flats with a pencil skirt?

I have a wonderful dark jean pencil skirt that I have never worn because I always thought one needed to wear heels with that type of clothing, and I don't wear heels (2 small kids, really casual office, *comically un-cordinated* and lack of funds for a 'heels only' wardrobe)

Then yesterday I saw a girl with ballet flats and my jean skirt-she looked great! Can/Should I try it or was it just her confidence that made it a Do?

Pointy or ballet flats? Fitted shirt or slouchy?
posted by Frosted Cactus to Clothing, Beauty, & Fashion (30 answers total) 5 users marked this as a favorite
Closed toe flats or even wedges are fine. Something with an accent or a pop of color.

Fitted shirts always. Slouchy = sloppy.
posted by asockpuppet at 10:18 AM on September 26, 2011

I'm wearing flats with a pencil skirt right now. I like pointy flats, but I lean towards a sort of vintagey style. Ballerinas work well, too. And you can do either a fitted top or some volume depending on your mood.

My shoes look like this.
posted by chatongriffes at 10:20 AM on September 26, 2011

I feel much more pulled together when I wear pointy flats, which made me feel confident enough to wear them with skirts.
posted by Zophi at 10:21 AM on September 26, 2011

Of course you can wear flats with a pencil skirt... I don't even think that's the tiniest bit strange. Pointy is probably more "professional", but ballet flats is fine. And in general I prefer fitted shirts all the time, but there's no real problem with slouchy with something fitted like a pencil skirt except that you look less put together.
posted by brainmouse at 10:22 AM on September 26, 2011

a jean skirt of any style can be worn with flats. i'd go with a fitted shirt, and flats that are like ballet flats but more structured. of course, i hate pointy shoes on me, so that probably influences my answer.
posted by nadawi at 10:23 AM on September 26, 2011

For clarification, I mean this by volume for the top.
posted by chatongriffes at 10:23 AM on September 26, 2011

I wear ballet flats with just about everything. Denim is inherently more casual, so I think you could get away with a lot more. Go for it!
posted by TooFewShoes at 10:23 AM on September 26, 2011

I'd go something that stays pretty close to your body but isn't super fitted (as in not too tight), and I'd avoid really slouchy unless you're really, really skinny. No poncho type tops.

What about something like this cowl sweater (less pricey, obviously, but this look is all over lower priced stores too) or this shirt with ballet flats? (Disclaimer, I like very few pointy flats, and to be successful I usually think they need some embellishment on them, which makes them less versatile, while a perfectly plain ballet flat looks fine to me.)

But really, part of the beauty of that skirt is that it is so versatile - you almost can't go wrong. It's a classic shape, the dark denim makes it dressier but not too dressy, and dark denim goes with so much!

So yes, do it!
posted by mrs. taters at 10:24 AM on September 26, 2011

Flats with anything. More often then not I'm wearing long flat boots, but a pencil skirt lends itself well to big clompin' school marm shoes. Can you pull off the sultry lieberrylady look?
posted by Trivia Newton John at 10:26 AM on September 26, 2011

If the skirt is closely fitted and the slouchy shirt is lightweight, I could see that working nicely as a casual look, but if you're thinking of wearing it to the office, something fitted but not tight would likely feel more appropriate (at least until you get comfortable with the idea of wearing the skirt with flats). Pointy shoes generally look a bit dressier than rounded-toe (but a lot obviously depends on materials and workmanship, too).

Definitely get the skirt out of the closet and start trying it on with flats - I think you'll find you have a lot of options.
posted by EvaDestruction at 10:32 AM on September 26, 2011

Of course you can! Flats go with everything, I say. Audrey Hepburn and countless podiatrists would agree.

I prefer pointed flats; even a slight, rounded point is fine. Then again, I'm biased: although I like ballet flats, the ones with perfectly round toes look stumpy to me.

If you go the ballet flat route, look for a pair with a little bit of shape to them - a slight inward contour along the sides or at the sole - rather than flats that are cut just straight across. They usually look a little more polished and less slipperlike.
posted by Metroid Baby at 10:41 AM on September 26, 2011

Oh yes, flats with pencil skirts FTW! This is one of my favorite looks (and I'm short/petite; you don't have to be skinny and long-legged to pull it off). I wear ballet flats (my favorite pair is black suede); I think that's fine in a casual office. Pointy flats, ballet flats - go with what is most comfortable and what you love.

You're in luck with that "dark jean" wash - the darker the jean (pant or skirt) the more office-worthy it is.

Tights with jeans skirts and flats tend to look more professional than bare legs, especially in winter. I'm biased; I hate going bare-legged because I have pasty legs and feet prone to blisters. There are those who rock the bare legs, and if you are one of those, that's great.

As for slouchy vs. fitted tops: How tall are you? The taller and smaller-bosomed you are the slouchier you can go without looking boxy or stumpy. I personally go with minimal to no slouch because I am petite and short-waisted and slouchy tends to make me look really dumpy. If you're small, short-waisted, and/or big-bosomed, a little slouch goes a long way; I can do a lightweight sweater with some slouch but then I make sure everything else is super-lean - I'd wear my jeans skirt with black, brown, navy or dark gray tights and shoes. Otherwise, fitted is the way to go.

A lovely look with a pencil jean skirt is one of those horizontal striped French sailor shirts as long as it's not too slouchy. Any kind of polished knit top or sweater is a terrific look with a pencil skirt and flats.
posted by Rosie M. Banks at 10:55 AM on September 26, 2011

Another one currently wearing flats (ballet, silk) with a pencil skirt. It's a standard work look for me. I hate the way my feet look in pointy flats so I never wear them.

I think on the whole my legs probably look a little nicer when I wear heels with a pencil skirt but heck, my legs look pretty darn good in a pencil skirt no matter what I'm wearing with it, and flats are easy.

And I think you can wear whatever you want on top, adjusted for your body type and where you're going! I tend to go slim on top when I go slim on the bottom because I'm more top-heavy than most, but plenty of people can do slouchy on top and slim on bottom and look fierce.
posted by mskyle at 11:04 AM on September 26, 2011

Flats with a pencil skirt are fine. Easiest to pull off (in my experience) if the skirt is at the knee or slightly higher; either pointy toed or ballet are fine as long as they're not too clunky and have a bit of polish to them (style-wise, that is; they don't actually have to shine).

I think the slouchy vs. fitted top thing should be determined based somewhat on the fit of the skirt. A shorter, more fitted skirt may be balanced out a little with a slightly fuller top, while a slightly longer skirt, or one with a heavier fabric, may be balanced more with a top that's on the fitted side. This is also what works for my body type (tall, skinny, small bust), so if you have a different body type, YMMV.
posted by scody at 11:08 AM on September 26, 2011

My default outfit is a dark denim pencil skirt, a top, a cardigan, and flats--usually ballet. You'll be fine.
posted by elsietheeel at 11:08 AM on September 26, 2011

Flats rock, why on earth wouldn't anyone wear them with anything? Go for it, you'll look fab, and your back will thank you.
posted by freya_lamb at 11:19 AM on September 26, 2011

I have a dark denim pencil skirt like you're describing. I wear clunky lace up flats with mine and they look just fine. Otherwise I wear flat calf high winter boots, or only very occasionally chunky high heeled boots. Nothing pointy or fussy, I hate that look anyway (particularly with denim). On top I'll wear anything from a teeshirt to a nice tailored shirt, but it's a fairly dressy skirt so I usually lean more professional there.
posted by shelleycat at 11:34 AM on September 26, 2011

Another thought on the slouchy: A more slouchy or loose-fitting cardigan, worn as a jacket, open or halfway buttoned over a tighter shirt is a great look no matter how tall or thin you are. The only thing is to be sure that the cardigan is a fine knit like cashmere, not a big cable-knit heavy wool sweater that might swallow you up if you're smaller; and wear it unbuttoned or half-buttoned.

I like the look of cashmere cardigan, worn open over a more fitted sleeveless shell (knit or woven), with a pencil skirt and flats. A bonus is the cashmere is cozy if your office is one of those where they blast the air conditioner.
posted by Rosie M. Banks at 11:53 AM on September 26, 2011 [1 favorite]

You don't mention the length of the skirt, but the flats+skirt combination is most flattering where the skirt hits right at your knee, and least flattering where it hits below the knee at or near the thickest part of your calf. If your skirt is longer than knee-length, getting it shortened will improve the look by approximately one million percent.
posted by mchorn at 12:24 PM on September 26, 2011

I wear my denim pencil skirt with flats. Loafers, ballet flats, Mary Janes, Keens, Tevas, boots, etc. I wear it with a chunky sweater, or a cardigan, or a tshirt & cropped jacket. I have a strong sense of what looks good on me, and what I like, and it doesn't have much to do with what's 'in fashion.'
posted by theora55 at 12:28 PM on September 26, 2011

If long legs yes, if short legs no because you will look comically stumpy.
posted by tel3path at 12:33 PM on September 26, 2011

Hell's yeah. This fashionista has it down to a science!
posted by thinkpiece at 1:05 PM on September 26, 2011 [1 favorite]

Response by poster: You guys are great- thanks. I'm wearing it tomorrow
posted by Frosted Cactus at 1:05 PM on September 26, 2011

Tons of examples here!

Pink shirt

Brown flats with slight wedge - but the effect from the front is just like flats
Pointier flats
Red flats
posted by barnone at 1:34 PM on September 26, 2011

Red pencil + nice flats = tres chic!
posted by barnone at 1:52 PM on September 26, 2011

posted by freshwater at 3:44 PM on September 26, 2011

It worked for Audrey Hepburn, why can't it work for you?
posted by Lesser Shrew at 4:37 PM on September 26, 2011

If long legs yes, if short legs no because you will look comically stumpy.

Unless your legs are very short, it's a doable look if you've got (a) shapely calves, (b) pointed flats with a relatively low vamp, and (c) a pencil skirt that's tapered and hits right at the knee.
posted by thisjax at 7:13 PM on September 26, 2011

I'm short, with short shins, and this is essentially my summer work uniform. I do generally wear something a little more office-y than usual with my denim skirt, but that's it.
posted by sepviva at 7:28 PM on September 26, 2011

I live in flats and agree that they go with anything! With that said, I prefer the way heels look with pencil skirts. That's just personal preference and would absolutely not look twice at someone rocking flats. It works fine. Comfort is key. Go for it!
posted by allnamesaretaken at 9:26 PM on September 26, 2011

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