Thursday, August 20, 2015

Dare to Wear: Sneakers and Pencil Skirts

Dare to Mix
Contains affiliate links

Tommy Hilfiger polo top

MANGO zipper pencil skirt
$31 -

Converse navy blue sneaker
$39 -

H M knapsack bag
$39 -

Not to long ago I did a post about wearing sneakers with skirts and dresses. Most of the outfits I posted were not difficult to imagine or style. Thats because I chose dresses and skirts that were considered more on the casual side. But a trying to wear sneakers with a skirt that women usually wear with their professional look is very hard.  

Pencil skirts are not traditionally worn with sneakers. Most women wear them with heels or dressy flats. But a video as well as a Polyvore contest inspired me to dare myself to come up with a few looks and inspiration to put together two opposites (Dressy and Dress down). 

How To Style A Midi Skirt Outfit?

For Fall pair a comforty sweater to blend a dressy skirt with casual shoes.

Untitled #767

A graphic sweat shirt pulls the look together. 

$20 -

Playful Streetstyle

A leather jacket also makes the pencil skirt less office and more street style.
Playful Streetstyle (clipped to

Tricky Trend: Sneakers and Pencil Skirt

A plaid shirt is another way to pull the sneakers and the pencil skirt together. 

H M motorcycle jacket
$47 -

Pencil skirt
$20 -

Converse black shoes
$70 -

I think this is is my favorite look!

Skirt (see more pencil skirts)

Untitled #766

$13 -
$47 -
$23 -
$31 -

Can't go wrong with a denim vest to make a dressed down look.

Vest (see more vest waistcoats)

Tricky Trend: Sneakers and Pencil Skirt

A button down blouse can be dressed down as too! 

H M green blouse
$19 -

Dorothy Perkins pencil skirt
$34 -

Keds lace up shoes

Patchington beige handbag

Bracelets bangle
$11 -

Tommy hilfiger glasses

The New Skirt Style You Should Be Wearing (And How To Wear It!)

A girl sparkly pencil skirt even looks great with sneakers and slouchy sweatshirt. 


  1. love this post, i can't wear high heals just sneakers, Mary Jane, Boots as i have to wear a orthotic in my right shoe and i wear a AFO on my left foot. So i wear trainers with skirts and dresses more than most.

    1. I know quite a few people who cannot wear heels. I do not wear heels that much any more either because I fractured my foot and some heels seem so uncomfortable to me still. So I am glad that fashion is getting more realistic and accepting that fact that every women can wear heels!

  2. I love this!!! I've never thought about pairing sneakers with a pencil skirt and let it look so good! I've always seen it in magazines but to see other women wear them and the way you style them ahhh Its inspiring! Now I just need some cute sneakers to pair with my skirts haha! I'm getting ideas!!!

    Jasmine :)

    1. I never really thought of pairing sneakers with a pencil skirt until I saw the E! fashion video. The stylist mentioned mixing something dressy with something casual. I thought that was interesting and maybe I should try to come up with some ideas of my own. When I saw some of the looks I found I thought the same thing, time to find some cute sneakers to wear with my pencil skirt! I hope there is a sale someone where on sneakers!

  3. Thank you for sharing these new looks. I love how the models look dressed in skirts and sneakers but not so sure that I could pull off that style. So glad you visited my blog today too.

  4. Maybe you will like our pencil skirts and loose fitting 3/4 sleeve tops

  5. I absolutely love this unexpected link. Especially the polka dot skirt with the black sneakers and sweatshirt, adorable!!! I think I'm going to try it.
    Thanks for linking up with us.

    1. Thanks! I am glad you liked the looks! Thanks for hosting such a great linkup.

  6. I like the thought of this dichotomy of's still hard to wrap my head around it, but I may try it one of these days! I like the sneakers that don't look quite as athletic (like keds or converse) jodie

    1. Keds and converse are my favorite sneakers too because they look so great with dresses!

  7. Great post idea! I like the outfit with the polka dot skirt best, although I'm still unsure if I would wear actually running shoes with a skirt! Your post has inspired me to try it though:)


    PS: Stopping by from King Maker blog's link up!


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