I recently helped a client create a set of outfits around a knitted midi skirt (shown on the right), which is another example of how the outfit creation process can begin with a single item. This client is a tall hourglass with a broad shoulder line. Her lifestyle is casual and she does not wear heels. She loves having a small wardrobe with many mix-and-match possibilities that she can repeat over and over again. The more outfits we create with fewer wardrobe items, the happier she is. 

By following the same steps that we used to create outfits around a pair of trousers, we arrived at several casual skirt ensembles in about half an hour. The striped pencil skirt outfit formula for Mums on the go served as a frame of reference throughout the process.

Assess Fit to Set the Scene

I was with my client when she bought the skirt, but for good measure we assessed the item again to make sure that she was still feeling the skirt vibe for her casual lifestyle. After wearing only jeans, Ponte pants, leggings and shorts for years, the skirt was very much out of her comfort zone. But it was as comfy as a pair a pajamas and she was up for a change. The skirt fits in the same way as it does the model and covers her knees. 

Keep Troubleshooting Tactics Top of Mind

As we combined tops, toppers and footwear with the skirt, I had three troubleshooting questions top of mind and we used them to figure out why some combinations weren’t working.

1. Is it the length of the tops and toppers causing unflattering proportions? 
2. Is the contrast between the items, and the items and your skin tone, too high or too low?
3. Will the outfit look better with heels? 

Although my client does not wear heels, I still asked the question along the way when the outfit didn’t look right. If it’s a question of adding heels, we scrapped that combination and created flattering proportions in other ways. 

Select an Assortment of Tops

The next step was to pull out all the tops that might work from my client’s closet and lay them on the bed with the skirt. As I selected the tops, I was thinking about her needs: her comfort zone, how to evolve her look, how the outfits reflect her style descriptor, and the settings in which she’ll be able to wear the outfits. 

The neutral integrity of the skirt made all colours a possibility, so we didn’t feel restricted when it came to matching the black and white stripes with other shades. I stuck to regular length tops because those work best with this length of skirt. I left behind tops that did not provide enough coverage around the tummy area because my client is self-conscious about that part of her body. I also left behind the tunics because, although my client is tall, those outfit proportions would look better with heels. 

Since the skirt was already outside my client’s comfort zone, AND because she does not tuck tops into skirts, I headed straight to two solid short sleeved, scooped neck big tees in turquoise and pink. They were very much inside her comfort zone. She smiled and loved the idea of just throwing them on over the bold rugby stripe and looking extra relaxed in a skirt. I suggested that this was as casual as wearing clamdiggers with a tunic, and that she could wear this combination daily in warm Summer weather. It needn’t be reserved for dressier settings. 

Knowing that my client is an adventurous pattern mixer, and that stripes are a great pattern mixing vehicle, I pulled out a polyester-rich floral patterned top and panel printed tee with high-low hemlines to match with the skirt. Both pattens have black in them, which picked up the black stripe in the skirt thereby creating a cohesive visual. She liked the idea because it gave her more options to wear with the skirt. 

We then pulled out a few cotton sweater options. A boxy oversized V-neck in neon pink and a navy mesh style with a welt that required a camisole. Both looked great. So far, we had six tops to wear with the skirt, which was more than my client bargained for. To keep things simple we left it at that. Having too many top options can complicate matters. 

My client tried on all six tops with the skirt because looking at an ensemble on the bed is not enough. It’s extremely important to try on the complete combinations in front of a full-length mirror to check whether they are to your satisfaction. All the tops are “throw on” and therefore left untucked. No styling required other than the scrunching of long sleeves. 

Introduce the Optional Topper

Toppers are not essential, but a great option for cool mornings and evenings, or arctic air conditioning. Again, as I went back to select topper options, I was once again thinking of her needs. My client must feel unrestricted while driving and reaching in her toppers, so we eliminated all fitted styles except a white and a blue denim jacket that worked very well with the skirt. The denim jackets looked great, but my client wasn’t feeling them anymore. On to something else. 

My attention turned to soft and stretchy cardigans, because my client finds them very comfortable. I pulled out a cropped navy swingy cardigan with a short back and longer front, and a white cascading cardigan. Because there is no getting around the step of physically trying on the completed outfits, we tried both cardigans over all six combinations. Four emerged as winners. We liked the navy cardigan over the patterned tops and the white cardigan with the solid pink and turquoise big tees. 

I then hauled out a mixed media ink blue knit and pleather moto jacket as a third topper option. Although fitted, it’s stretchy, so comfort was assured. It turns out that the moto worked best of all, and was an option over all six tops. Bonus.

Ground the Outfit with Footwear 

An outfit may not need accessories, but it always needs footwear. There were two options for footwear here: casual ballet flats and sandals. No heels. So we pulled out a light turquoise pair of ballet flats, cream snakeskin flats, and two pairs of strappy gold sandals. The tapered length of the skirt did wonders to prevent the dumpy feeling a midi skirt can sometimes create when paired with a pair of flats. 

We started working the different footwear options into the outfits, trying them all on in front of a full-length mirror. We were both amazed at how well the light turquoise ballet flats worked with each outfit. My client’s beautiful light turquoise eyes bookended the shoes to perfection. The cream snakeskin flats bookended her blonde hair, while the gold sandals were an all-round flattering, leg lengthening slam dunk. 

For several of the outfits we found ourselves looking for a crisp pair of white flats to pick up the white of the skirt. And the snakeskin flats, although gorgeous, were not fast walking Mum on the go shoes. So we added a light and comfy pair of white flats to the shopping list.

Finish off with Accessories

Although I am outlining this process as a set of steps, it’s seldom this ordered in practice. In reality, we are trying on the accessories throughout the process as we get inspired. 

My client sticks to sporting one handbag a season, so we finished off each outfit with the same white tote. A wedding ring and white watch also accompanied all the outfits. With the solid tops and sweaters we added a long turquoise pendant necklace to pick up the colour of the flats, or stuck to a short lucite beaded necklace. We left the pattern mixed outfits sans jewellery because there was a lot going on already.

Evaluate the Outfit Shortlist 

I mentioned my client’s needs several times here, and it’s usually worthwhile to revisit those needs one more time with the final set of outfits. Since my client leads a casual lifestyle, we made sure that nothing that we put together made her feel too dressed up. After all, she was wearing a skirt as a busy Mum on the go for the very first time. 

I suggested she break in the skirt by matching it with the big tees and sweaters, and then start introducing the more dressy pattern mixed outfits later, when she’s more used to wearing the skirt.

Then there is the all important happiness factor. Despite our analysis of fit, proportions, style descriptors and settings, ultimately what makes a good outfit is an emotional thing. So at the end of the process, I ask my client questions to assess how happy she feels in the outfit. Does it feel fussy? Do you feel attractive, interesting and healthy in the outfit? Do you feel self-conscious? 

Sometimes though, you need to push the boundaries of your comfort zone and violate your happiness factor in order to take yourself out of a style rut and try something new. The important thing is to do this consciously. So wear the outfit if you know it’s testing your comfort zone, but don’t let it through if you have a nagging suspicion that something feels very off. 

Take It on the Road 

Evaluating an outfit in front of a mirror is not the final step. If you like it at home, you know it has great potential, but you have to road test the outfits in motion, in real weather, and in the intended setting before you can give it the stamp of approval.

Karl Lagerfeld stars in Mode Als Religion (Fashion as a Religion), a German documentary likening fashion magazines to the Bible, models to angels and consumers to followers.

Watch the first trailer for Mademoiselle C, a documentary following Carine Roitfeld during the making of the first issue of CR Fashion Book, the former Vogue Paris editor’s own magazine.

Currently in the making: The Fashion Fund. This six-part documentary will chronicle the selection process of the 10th annual CDFA and Vogue Fashion Fund, in which ten designers compete for a $300,000 cash prize. The selection committee consists of Anna Wintour, Diane von Furstenberg, Jenna Lyons, Reed Krakoff and Rag & Bone design duo Marcus Wainwright and David Neville.

Fab Links from Our Members

Author Jennifer Weiner allows us a peek into her wardrobe through these fun What I Wore descriptions. Joy dedicates this article to all the writers on YLF.

Lantana discovered Ageless Patterns, a rather whimsical website with useful resources for those of us who are into sewing and history.

“5 Ways to Make Your Staple Pieces Cool Again” appealed to Milehighstyle(Linda) because her little black dress, flats and cardigans haven’t been getting much love lately.

Angie enjoyed Sally’s post on Male Body Objectification. It’s fresh to see men as the object of discussion for a change. Sally’s message that regardless of sex or gender, all human bodies can be objectified, is food for thought. 

Wearing black and white together often feel a bit too much on texstyle, Bridgette’s post on why high contrast black and white isn’t always flattering helped explain why exactly that is.

CocoLion asks what we think of the current Birkenstock revival. She loves it when comfort shoes gain status within the fashion ecosystem.

This J.Crew ad made Nadya smile. Don’t you want to size all your handbags in units of bunny now?

Although Lyn* doesn’t agree 100% with Rebecca’s point of view, she found the blogger’s perspective on developing a sense of personal style — i.e. without taking the feedback of everyone around you into consideration — an interesting one.

Meet the Stiletto Whisperer: former shoe designer Victor Shu is teaching women how to walk in high heels. Sona appreciated the reminder that anything above a 3 inch heel can be dangerous.

Vildy liked that Rebecca Mielke asks some thought-provoking questions regarding how standing out with the way you dress affects both you and your environment.

A dress that says “There’ll Always be an England”. ManidipaM was intrigued by the story behind this propaganda dress from the World War II era.

It took all season to find the silk tee that was on my warm weather shopping list. I was looking for a pattern that tickled my fancy and a fluid fit. Diane von Furstenberg’s Becky print top made of stretch silk with blush toned leopard printed front panel fit the bill. I like the high neckline, tailored fit around the shoulders, and tight short sleeves. The straight cut that drapes back onto my torso was the next selling feature. Dressy, yet relaxed. It’s fun to sport a new-to-me silhouette because I generally stick to wearing a variation of three styles of top.  

The silk tee is a Summer item, but also a great layering piece that I can wear into early Autumn. And because Autumn is warmer than Spring, it earned a place in my wardrobe so late in the season. It effortlessly fits into my blush, black and cream business casual capsule, and looks as good with a faded pair of boyfriend jeans. I’m showing some of that capsule here by wearing it with a black Summer suit, blush moto, black pencil skirt, cream satchel and pony print pumps.   

This silk tee is best worn untucked, and since I usually bat for Team Tucked, this is a nice change for me. It’s a no-brainer matched with a pair of sleek black bottoms because of the roomy torso fit. My black suit provides a good support act for the upscale tee because of the cropped length of the pants. I can leave off the jacket when it’s hot, and pop it right back on for an air conditioned indoors.

I thought of my blush moto and its matchy-matchy potential as soon as I saw the pattern of the silk tee. I can mix up the suit by wearing the moto instead of the black jacket to lighten things up. It might seem odd to wear a leather jacket in Summer but it makes sense for always-cold me. First, this is a lightweight leather jacket, which makes it a perfect “indoor jacket”. Second, Summer mornings and evenings are cool, which makes a topper essential. And then there is my constant battle with arctic air conditioning when I’m shopping with clients or at a restaurant. I would be uncomfortably cold at some point during the day without a jacket over this breezy silk tee.  

It’s fluid tops like this one that have rekindled my love for tight skirts. My black pencil skirt has gone unworn for years, but because it’s a quality modern classic piece that fits well, I held on to it. I like the skirt paired with the tee because it de-bombshells the outfit. The pairing also looks a little like a two-piece dress because of the vertical flow of black from top to bottom. Bonus. I got a frock out the deal too. The black jacket that belongs to the suit and the blush moto both work just as well layered over the skirt and silk tee as they do layered over the cropped pants rendition.

In each case, I finished off the look with the same pair of pointy toe ankle strap pumps. The pony pattern lightens up the palette of the outfit and adds some pattern mixing interest. I’ve been wearing my new gold watch with black face non-stop since I bought it at the Nordstrom Anniversary Sale. It’s huge, and looks more like a bracelet than a watch. I fancy its masculine juxtaposition against a pretty and feminine outfit. I chose a cream satchel instead of a clutch, and wore my old retro black specs. No jewellery other than a gold wedding ring to match the watch.

I like the skirt and trouser outfits equally but for different reasons. The cropped pants outfit is practical because I can walk faster than when I wear a pencil skirt. The combination is also more on trend than the pencil skirt. I like the pencil skirt outfit because there is less black covering my legs, which suits me because I’m not that into showcasing black from head to toe. It’s also fun to wear “a dress” instead of pants. 

As I get older, it is as important to me to feel comfortable as it is to look modern and fashionable. If we were going to fashion week in September, a very tiring experience, I’d have worn the practical trouser suit rendition on the first day. Sufficiently breezy for the New York heat sans jacket. A topper option for cold tents. And shoes that go the distance for my fussy feet. All sorted.

The sheen on these booties is a lot more subtle than the ultra mirror-shiny sparkle of the sci-fi trend. And they make a nice change to the black footwear that will be trending strongly for Fall and Winter 2013. 

1. Seychelles Lucky Penny Boot: A casual metallic boot is hard to find, and this one fits the bill. Not overly pointy, but not all that round either. Appropriately distressed for team “rough around the edges” who have the magpie gene. A nice update for Autumn and Winter Mums and gals on the go. Fab cushioning footbed and runs true to size. I vote pewter or gold. 
2. Donald J Pliner Turk Bootie: On trend, dressy, sleek and great for the office. 
3. Softspots Sherry Boot: A subtle bronze for those who like earth tones. 
4. Anyi Lu Audra Boot: Divinely comfortable, good arch support, and impeccable quality. A rugged yet refined biker boot.
5. Chio Vieri Bootie: This shootie-bootie hybrid isn’t shiny, although the graphite silver colour option has depth and some sheen. 
6. Cole Haan Allen Bootie: A brushed gold Beatle bootie complete with comfortable Nike Air technology. A good shoe for travel. 
7. Dolce Vita Nimbus Boot: A shiny heel is one way to go if metallic booties are too much sparkle. This zebra darling reminds me of Nicholas Kirkwood’s footwear, but at a much more affordable price. Quite the eye catching ped.

It might be hard to think of booties in the middle of Summer, but for some, bootie wearing season is just around the corner. Because Fall and Winter are my dominant seasons, I find it fun to have a new pair of boots or booties waiting in my closet ready for action.