J.Crew Pencil Skirts on Sale: How I've Been Wearing Them

It can be pretty maddening when J.Crew rolls out a brand new selection of clothing only to send it to the sale section 10 days later. Sometimes it feels like purchasing at full price is a waste of money...but I still do it when I think that something might sell out in my size or my preferred color. However, with a little patience (and a lot of jungle panther-like stalking), you can get great deals on some of J.Crew's classic pieces like Jackie Sweaters, Cashmere Long-Sleeve Tees, and No.2 Pencil Skirts. There have been a lot of pencil skirts on sale recently, and I've taken full advantage since they have become real work-wardrobe workhorses for me. In case you've picked up some of these skirts as well and are looking for new ways to wear them, here are a few examples of how I've been wearing mine.

FYI: All of the following personal images were taken in the Executive bathroom at my office, hence the snazzy bathroom decor.

No. 2 Pencil Skirt in Medallion Paisley


This skirt is currently sold out online, but keep watching the sale section and I'm sure it will pop back.

The Medallion Paisley Pencil was a really great buy - I've probably worn it once a week since I purchased it. The material is a strong but lightweight cotton twill, almost like denim, but the simple pattern and shape make it appropriate for the office. I bought it in a size 6 and it's fairly loose. I probably should have sized down to a 4, but it's more comfortable in the larger size when I'm sitting at my desk all day.


Late March and early April brought cooler temperatures to Georgia, so I was able to pair this skirt with some of my beloved cashmere sweaters for work. The purple and white print of the skirt compliments many solid-colored tops like gold, tangerine, and blush.


Here I've paired the skirt with two of my most favorite wardrobe staples: the Schoolboy Blazer in Navy and the Selvedge Chambray shirt. The shoes are Calvin Klein - about as basic as a navy work pump can get, but they are comfortable and polished.


No. 2 Pencil Skirt in Basket-Weave Tweed, Marine Blue


I reviewed this skirt in a previous blog post HERE.


I've worn this skirt with navy sweaters and button-downs, but here I decided to go a little bolder and pair it with my Talitha Blouse in Vintage Berry. I can't get away with wearing very much jewelry at work, but J.Crew's navy Sunflower bracelet adds a fun little pop of color.


I might be one of the few people who really liked the heavy, stretchy knit of the Jackie Pullovers, but I bought 4 of them and they've been in heavy rotation ever since. This simple combination of skirt and sweater is dressed up a bit with an old J.Crew golden chain necklace, double looped at the throat, and a leather and gold bracelet that I purchased at Monkees in Southern Pines, NC. The shoes are my trusty Nine West Austin pumps. They're comfy, cheap, and come in about a dozen work-appropriate colors.


No. 2 Pencil Skirt in Gardenshade Floral


Also currently sold out, also certain to pop back.

As far as sizing goes, this skirt is comparable to all of J.Crew's other pencil skirts. The quality is great - it's fully lined and the silky, slightly stretchy cotton barely shows wrinkles at all by the end of the day. I honestly wasn't too sure of this skirt when I pulled it out of the shipping box since the colors were so much more..."muddy" in real life than they appeared on the website. However, I started pairing it with tops in my closet and discovered that it looked great with my Jackie Cardigans and Perfect Shirts in various shades of pink and blue.


Worn here with a Pale Coral Jackie Cardigan, random TJ Maxx tee, and an old gold J.Crew skinny leather belt. It also looks great with blush and navy Stretch Perfect Shirts.

No. 2 Pencil Skirt in Ultra Eyelet


I bought this skirt at full price in the Chili red color when it first rolled out, and I'm glad that I did because it's now sold out in that color. The Navy version is now on sale.

Maybe it's just me, but there's something about wearing a red skirt that makes you smile when you look in the mirror. I LOVE this skirt. I was reluctant to buy it at first because of the nature of eyelet (it catches easily on things) combined with the nature of me (a.k.a. Mayor of Klutzville). But the cotton is smooth and stretchy, and there is plenty of give to the fabric. A lot of reviews mentioned the "shadow effect" at the inner thigh area that occurs beneath the lining and shows through the eyelet layer, but it doesn't bother me. It comes off more as visually interesting than "Hey, here's my crotch."



The Chili Eyelet skirt looks great with blue, white, and camel, and I also like pairing it with gray. Here I've gone for more of a retro ladylike look by combining the skirt with the shell portion of a gray Jackie twinset and a white cotton blouse with short puffed sleeves. The shoes are gray leather skimmers that I got at Target ages ago (I knew I would be running around a lot that day), and the necklace is from Madewell.



This is one of my best popback scores: the Scoopneck Blouse in Seine Stripe. I was afraid that the striped top paired with the red skirt would have me singing a certain Lee Greenwood song all day, but the fact that the lighter colored stripes are taupe instead of white or cream ensure that the outfit is not too "theme-y". I'm wearing the same gold chain necklace as in the second Basket-Weave Pencil Skirt image above, but not looped this time.

Have you purchased any of these pencil skirts on sale? How are you wearing them? Please share - I love to hear your ideas!