Ensemble: Relaxed Pencil Skirt and Pullover

Many of my clients enjoy wearing a tailored pencil skirt outfit because the combination generally looks dressy, professional and flattering. But they don’t necessarily want to look too dressed up and bombshell, which is often the case when you pair a formfitting pencil skirt with a tight top and pair of heels. So we look for ways to “de-bombshell” the pencil skirt for days that require a more relaxed vibe. 

There are many ways to relax the pencil skirt, and I’ve started the ball rolling here with three tonal renditions. The oversized pullover is at the heart of de-bombshelling the outfit. The ensembles become more casual from left to right. I’ve used solids, but by all means incorporate patterns and use any colour palette. Pairing the pencil skirt with the same colour pullover creates a two-piece dress effect, which I personally think is a great look. 

Here are the components: 

Pencil Skirt: Choose a pencil skirt, either dressy or casual, at a length that tickles your fancy. Some pencil skirts taper more dramatically at the side seams like a tube skirt, which adds more structure to the outfit and curve to your silhouette.  

Pullover: Choose a fluid or oversized pullover in a chunky or fine gauge. Choose a style with a neckline of your choice. Roomy pullovers with asymmetrical hems, high-low hems, split hems, and welts tend to work best because they add a little structure to the slouchy integrity of the top. Semi-tucking a fine gauge baggy pullover, thereby shortening its length, works well if the pullover is long. Scrunching sleeves to reveal forearm skin adds further structure. 

Swingy pullovers with a trapeze silhouette look quite nice over pencil skirts. Their volume is on the hem as opposed to the torso. 

Footwear: Pumps and ankle strap pumps are fab dressy options. Tall tailored boots with heels are great too. Heeled booties are easy, and wedged booties dress the look down even further. Pointy toe flats and loafers are another way to go. 

Wearing heeled booties with a notched and narrow ankle opening creates a longer leg line. Feel free to wear hosiery that matches the colour of the booties, or your skin tone. 

Accessories: Finish off the look with a bag, eyewear, jewellery and watch as desired. A bib necklace works well over a fine gauge pullover.

Ensemble: Relaxed Pencil Skirt & Pullover

Here’s Olivia Palermo sporting the look with a semi-tucked slouchy burgundy turtleneck, pencil skirt, ankle strap pumps, clutch and bib necklace. Choose a trench coat or longer wool coat as a topper.

Link Love: Tomboy Style Tips

If you’re looking for inspiration on how to incorporate tomboy or androgynous touches into your outfits, then this Refinery29 roundup of 24 Too Cool Tomboys in San Francisco might be just the ticket.

J.Crew Director and Executive Creative Director Jenna Lyons shared some tips on how to pull off a menswear-inspired look with Lucky Magazine.

Lizzie Garrett talks about the intersection of makeup and tomboy style, and asked celebrity makeup artist Toby Fleischman for suggestions on how to create a natural daytime look.

Fab Links from Our Members

Deb lets us know that this article by Invisible Woman about selfies for the fifty and over crowd has some good points.

Sally lists the danger of pre-made outfits, and talks about the photographed body. Angie thought both posts were interesting reads.

For those of us who were fans of the series back in the ’90s: Vildy got a real kick out of A Ranking of All 118 Sweaters Seen on Twin Peaks.

This recent article in the Wall Street Journal on loafers reminded Joyce of some of Angie’s picks. Joy adds that she never thought of loafers as a youthful shoe though.

HiggsMistress reports that there is a new top dog in menswear: Bodhi, the Shiba Inu. Fashion brands are taking notice and are collaborating with him for their ad campaigns.

Bj1111 came across this article on the tyranny of choice. She says: some forum members “have mentioned that it’s tiring to think of all of one’s clothing and have to fit in a wear for all the items during the season. A uniform is so seductive because it frees your mind to think about other things.”

Diane G thought this Fashion Tag post might provide useful inspiration for those ladies wanting to try some long cardigan looks.

Updating Your Wardrobe Essentials

Wardrobe essentials are indispensable staples without which your wardrobe would not function. They are not to be confused with wardrobe basics, which are items like underpants, bras, camisoles, shapewear, socks, sleepwear, loungewear, hosiery and thermals. Wardrobe essentials are usually very versatile, simple in design, and current. 

Wardrobe essentials are not necessarily the most interesting part of your outfit but they are a very important ingredient. They are like the foundation of an outfit, or the glue that makes the other pieces come together in a cohesive whole. If your wardrobe essentials aren’t in place you will probably end up with many more closet orphans. They make the rest of your closet a lot more wearable.

I do not believe in a universal list of wardrobe essentials because our needs are different. I prefer to suggest a personalized list that is suited to your lifestyle, climate, body type and style persona. T-shirts might be your button-down shirts. Stud earrings might be your oversized watch. V-neck sweaters might be your turtlenecks, and shorts might be your jeans. Remember that the list should be flexible, and should be open to change. 

It’s extremely important to ensure that your wardrobe essentials are current. Like other wardrobe items, they have an expiry date, and should be revisited seasonally to ensure that the pieces fit, are fashionable, suit your needs, work with the rest of your items, and are in good shape. 

My list of wardrobe essentials has changed slightly over the years as I’ve simplified my style and accommodated my evolving style preferences. A black pencil skirt, Converse sneakers, tall dressy boots, ballet flats, and a little black dress are no longer on the list. I prefer dressy black trousers to a pencil skirt, and dressy black separates to a LBD. For comfort reasons I have moved away from Converse sneakers, and switched from ballet flats to loafers. And I now prefer to wear casual, flat knee-high boots as opposed to dressy tall boots. 

In some cases the items that remain on my list have been updated to a more fashionable fit, colour or cut. That’s one of the ways I inject the Modern back into my Classics. 

  1. Button-Down Shirts: Roomy fits reign supreme and make the rest of your outfit look more fashionable. I held onto a few fitted silhouettes, but for the most part replenished my shirts with a baggier look in white, shades of blue, and plaid. Button-downs are “my T-shirts” and work well worn on their own tucked into bottoms with a belt, or layered under knitwear and jackets.  
  2. Turtlenecks: Few items make me feel as fab as a fine gauge turtleneck sweater because they work well with my very long neck. Plus they keep me warm, look polished, and layer extremely well under jackets. I held onto a few fitted styles because they work well with flared skirts, but added simple neutral turtlenecks in fluid and oversized fits to keep things current. 
  3. Jeans: I prefer wearing white jeans to blue jeans for a multitude of reasons and therefore expanded my white jeans capsule this year. Now I have more pairs of white jeans than blue jeans, which reflects my dressing habits, and prevents laundry bottlenecks. 
  4. Dressy Black Trousers: Black cigarette pants and dressy black flared trousers continue to come in handy. I’ve been wearing the same pieces for four years and they’re still going strong.
  5. Moto Jackets: I’ve had moto jackets in my wardrobe since the ’80s, and have updated their silhouettes accordingly. I wear my two black moto jackets very frequently and with just about any combination. One of them is five years old and the other eight years old, whittling down the cost per wear to nothing. Both fits are a little looser than tailored and therefore look completely current. I added a white moto jacket to my capsule this year, and hope it has as much longevity as its predecessors.  
  6. Blazers: I still wear my old grey pinstripe, two button Theory blazer that’s part of a suit. It does not look dated because it’s on the fluid side of tailored, and very simple. Last year I added an ink one button Theory blazer to my essentials capsule to achieve a more fashionable look. It has proved to be very versatile, and does not crease. I wear it for plane travel with a pair of jeans and feel polished and pulled together at the airport. 
  7. Denim Jacket: I updated this item two years ago by choosing a roomier fit with two-toned black mixed media sleeves. My tailored denim jackets are sitting in the holding zone. 
  8. Trench Coat: I have tailored citron and cream trench coats that I wear fairly frequently. Both are many years old and I love them just as much now as I did when I first got them. Neither looks dated and they are still in good condition. I passed on my black trench coat two years ago because I never wore it. I’m just not a black coat gal.  
  9. Tall Flat Riding Boots: I have a black and grey pair of casual flat riding boots. Both are several seasons old, but they still look current if I wear them with a trendy support act. 
  10. Oversized Watch: I added another oversized gold watch to my capsule last year because I fancied one with a black face. I have four that I interchange daily. 

If you haven’t already done so, consider compiling a list of wardrobe essentials. Some people can work completely from intuition, but for most the structure is a big help when it comes to building an effective wardrobe. When clients call me for an outfit creation session because they’re battling to create outfits, it’s often a case of missing or dated wardrobe essentials. They might not be the most exciting items to shop for, but they transform items into outfits. Do keep them current and don’t feel bad about spending a significant portion of your fashion budget on them.

Roundups

Simpler Items

This week's list of top picks list is about basic pieces.

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Assorted Items

Items for Summer, both in and out of air conditioning.

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Casual Summer Vibes

This week's top picks are good for a casual Summer vibe.

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Summery Earth Tones

These items are for those who like to wear casual earth tones in warm and hot weather.

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Hints of Spring

Some tried-and-tested winning items to refresh your style for Spring.

Read More

Dressier Items

An assortment of dressier top picks might be just what the doctor ordered.

Read More

Weekly Roundup: Dressier Casual Items

These casual pieces are dressier than T-shirts, flannel shirts, sweatshirts, slouchy hobos, rugged boots and track pants, but just as relaxed. They’re also a little different from most of the items at mainstream retail at the moment, which is quite refreshing. 

  • Bobeau Print Front Raglan Sweatshirt: A silk front sweatshirt with a digital tree print. Great on a larger bust, shorter neck and short waist. Combine with jeans and booties, and Bob's your uncle.
  • Zara Combined Leather Blucher: A sassy pair of two-toned flat oxfords that are quite comfortable. Boyish Fabness.
  • Elizabeth And James Women's E-Cosmo Ankle Boot: Sci-fi low-heeled wedge booties in soft leather. Comfy, fashionable and suited to low volume ankles.
  • Fossil Sydney Satchel: Small satchels in forest green are hard to find, but this one fits the bill. Doubles up as a crossbody bag. Well made.
  • Loeffler Randall Snakeskin Envelope Flap Lock Clutch: The prettiest forest green clutch I've seen all season. Looks as good with jeans and trousers, as it does with a cocktail dress. Holds more than you think.
  • Josef Seibel 'Kylie' Pump (Women): An extremely comfy low-heeled oxford with an Arty vibe. Suited to low and regular volume feet. Nice in black but fresher in brown. Fab pointy toe.
  • Zara Soft Bowling Bag: A fashionable forest green bowling bag for those who like to pack lots into their handbag.
  • UNITED NUDE Jacky Booties: Colour-blocked cognac is a good thing. Gorgeous heel and quite comfortable. Also available in black.
  • James Jeans Ponte Combo Blazer: A Ponte knit tuxedo blazer in ink is unusual, and more comfortable and casual than a woven version. Love the mixed media vibe and one button styling. A true Modern Classic, and great over dresses too.
  • BCBGMAXAZRIA Arelia A-Line Coat: I'm reminding you about this incredible jacket that made my top picks list for Spring. It's one of those pieces that changes the landscape of your wardrobe. It's heavenly over bootcut jeans and trousers, or straight legs. Just as nice over a sheath dress. It's suited to curvy hourglasses and pear shaped body types, and best on regular height and tall gals.

Remember that casual pieces can be dressed up or down with the right support act, which makes them a lot more versatile than you might expect.

Outstanding Outfit Bloggers

Petite Chic in Boston

Boston-based Jean Wang (late 20s) loves pearls and stands just under 5 feet tall. She is a CFA working in financial advisory, and blogs about fashion, lifestyle, and fit challenges for petite women on her blog Extra Petite. Jean’s style is impeccably polished, very chic, ladylike and classic with modern accents. She wears heels almost daily, likes colour and pattern, and is a fan of mixing high and low-end style. Jean is a stickler for fit and very knowledgeable about alterations, so her blog is a great go-to resource for fellow petite ladies looking for inspiration.

“I gravitate a lot towards classic and feminine styles, and I love mixing pieces (both new and pre-owned finds) from all different brands and price points. Five years ago, I was looking to build a more mature wardrobe that would help me transition from college kid to professional woman. Back then my style was a little more conservative, and over the past few years I’ve slowly become more experimental with colors, textures, and silhouettes.”

Boston Jean - 1

I was sold the minute I discovered that Jean is a pearls gal, like Angie and I. I adore the play on shapes in this French flair outfit: the oversized round pearls emphasize and complement the square neckline of the tee and crisp pleated skirt. The body con fit of the cropped tee in classic black and white stripe contrasts nicely with the elegant movement of the skirt. Jean altered the elastic waistband and took in the sides to achieve perfect fit. The bright peachy pink d’Orsay pumps and Summer hat add girly pizzazz. The blush pebble tote keeps things in the pink colour family without being too matchy-matchy with the pointy toe footwear.

Boston Jean - 2

Boston Jean - 2

Jean is on Team Mixing High-End with Low-End Pieces. Here she combines an H&M sleeveless fit-and-flare frock with a navy Theory trench. This shade of blue makes the mustard, navy and cream abstract pattern of the dress pop even more. Fab! The torso of the dress was slightly too long on petite Jean, and the waist an inch or two below her natural waist. So the belt worn higher is a clever, quick fix to visually raise the waistline. Leaving the coat open but tying the belt in a pretty bow creates a long line, showcases the fun pattern and fits right in with Jean’s ladylike and super polished style. Our blogger is sporting black heels that bookend her stunning dark locks. The clip-on bows are a fun nod back to the coat’s belt. The 66 inches long pearl necklace is wrapped three times and further enhances the ladylike vibe.

Boston Jean - 3

It’s unusual to find a ponte knit blazer in this light powder pink colour. It looks beautiful with the light-wash relaxed fit straight leg jeans. The rolled cuffs give us a better look at Jean’s leopard print pumps, which spice up the soft colour palette. Sporting distressed denim is an effective way to dress down a blouse and blazer outfit for casual days. The tucked fluid fit front pleat blouse adds delicate structure and extra polish. The caramel tote has clean, simple lines, and is a fun contrast against the pearl party up top. The multi-layered necklace in white, silver and gold is a statement piece, and just chunky enough to not overwhelm our blogger’s petite frame. Glamorous, oversized sunnies finish off the look.

“I love pearls because they never go out of style, plus are a safe bet when you don’t have time to think about accessorizing. My favorite pearl necklace is a long strand of ‘rope’ pearls gifted to me by one of my best friends — I love the versatility as they can be worn long, doubled or tripled up, knotted… the list goes on!”

Boston Jean - 4

Jean’s Burberry plaid felted wool coat is the star of the show in this outfit. This is my favourite look because I immediately fell in love with the fab navy, grey and charcoal check. Jean wanted something a little different than a classic long Burberry long Winter coat, and this belted beauty fit the bill perfectly. The asymmetric zip and silver hardware create modern soft edge, but are timeless at the same time. A blue ribbed turtleneck peeks out of the coat collar. Skinny black jeans are tucked into Hunter wellies with a wedge heel. The heel makes them dressier, which suits Jean’s style persona. The sheen echoes Jean’s lustrous locks. A black nylon tote with leather handles and charming beanie are the accessories of choice. The purple leather gloves — stunning with the blues and greys — are the luxurious finishing touch. 

Boston Jean - 5

Boston Jean - 5

An elegant and cosy outfit for a snowy day. Our blogger is using a leopard print cardigan as a top. Tucking the V-neck cardi into a wool above-the-knee-length skirt creates a longer vertical line when you are sporting dark hosiery. Wearing the coat open, and opting for a topper that picks up one of the colours in the top further emphasizes that effect. Jean picked a tailored ladylike wool coat with structured shoulder line in a dove grey that works beautifully with her dark hair. The faux fur collar is a chic and stylish addition that keeps her extra warm. Olive grey opaque tights also provide protection against the cold. They are high contrast against the cream skirt and taupe grey ankle boots, so they do create horizontal lines. But it works because of the heeled booties and shorter length of the skirt. Oversized tassels on a classic shape shoulder bag add a playful touch.  

Boston Jean - 6

This preppy plaid business casual look makes me smile. Jean is wearing an oversized plaid shirt borrowed from the boys in beautiful shades of red and green. She reins in the volume by popping over a chunky cable knit sweater that is more fitted but not tight. The forest green honey comb pattern looks fab with the colours in the shirt, and adds tonal textual interest. The turned-up cuffs on the shirt and pullover are a playful touch. Slim fit navy tapered ankle-length trousers keep the bottom part sleek and structured. The wool blend trench is a classic piece. The camel colour looks extra rich and luxurious against the deep green and red tones. Jean’s pointy toe pumps are a dark bronze metallic, which are unexpected and super fab! Her navy bag with gold hardware and gold nail polish pick up the same shade to create a harmonious whole. 

Be sure to check out the rest of Jean’s wonderful outfits over at Extra Petite, but first let us know what you think of our fabulous petite blogger’s chic and impeccably polished style.