The Westfield Style Manual, which was compiled by Stacy London of “What Not To Wear” fame and her team, is a fabulous little “how-to” style and shopping tool for Fall 2012. I picked one up at the Westfield Style Tour when I interviewed Stacy and have been browsing through it quite a bit. I’m impressed because it breaks things down in an attractive, simple and no nonsense way. Here are my favourite parts.

The outfit visuals are wearable, compelling, on trend, and affordable throughout. It’s extremely refreshing to see both expected and unexpected outfit combinations, as well as flat and low heeled footwear on models of all ages and sizes. LOVE that.

When I compared Stacy’s Top 10 must haves for the season with my own 13 Must haves for Fall & Winter 2012, we overlapped by five items. So interesting! 

Stacy has a great seasonal solution when clothing trends aren’t tickling your fancy: “Dip your toes into of-the-moment looks with accessories, and stick to my mantra: colour, texture, pattern and shine”. Think colour, texture, pattern and shine – and you’ll be fine. 

The minimalist in me enjoyed the identification of 5 Key pieces that will revamp your Fall wardrobe right now, and how to mix and match these items to create different looks. 

I liked the section “it’s so wrong it’s right”, which shows how to mix daytime pieces with evening wear pieces in edgier ways.

And last but not least, it was super fun to see fellow blogger and friend Dianna the Budget Babe model her looks for the manual on pages 39 and 51. Her killer smile is her best accessory of all. So fab! 

The manual is available at Westfield Style Tours, or online, and is well worth a look. It’s a fast, easy read with lots of visual encouragement along the way.

Whether it’s in a client’s closet or on a thread in our forum, as a fashion stylist I am often in the position where I have to decide whether an item is dated. In this situation the so-called “timeless items” are the most interesting because in reality there is no such thing as a truly timeless style. When we say something is timeless, what we really mean is that the style’s longevity is high. But the degree of longevity will vary. Put differently, “timeless” has an expiry date and that expiry date varies according to the specific style or item we are talking about. 

Timeless items are most often classics, vintage items, avant-garde items or iconic items. Here are my loose guidelines for thinking about their longevity.

Classics need to be updated to Modern Classics 

Items like tailored button down shirts, basic pencil skirts, classic trousers, bootcut jeans, biker jackets, Burberry-esque trench coats, tailored blazers, fitted turtleneck pullovers, pumps, single breasted wool coats, peacoats, striped T-shirts, sheath dresses, cashmere sweaters, ballet flats and flat riding boots are considered timeless inasmuch as they are always in style. Yet the actual silhouette, length and fabrication of these items can absolutely look dated after a time.

Updating these “timeless” pieces to “modern timeless” pieces is therefore essential. In my book, having a great sense of style means incorporating a certain amount of “now” into your look. That’s why classic items have to reflect the prevailing fashion era in order to be fab. 

Vintage items are timeless when worn with a big dose of Modern 

When we go back far enough in time, certain exceptionally well designed wardrobe items that are decades old are timeless when they are worn with an on-trend support act. After all, retro items are thought of as uber cool.

For example, a vintage flared ’50s skirt can look fabulous with a trendy leather jacket and shooties. A ’60s mod dress is great over a pair of skinny jeans and animal print pumps. A clutch handbag from the ’40s is stunning with a pair of trendy leather pants and modern classic button down shirt. A knee-length ’70s leather jacket is smashing over a drapey patterned dress. And wearing antique jewelry with modern classic separates is another great pairing. 

Avant-Garde items are often timeless

Avant-garde items are eccentric to the point that they could fit into any fashion era. People wearing them update their look decade after decade by keeping the support act either modern classic or very on trend.

Iconic items have the most longevity

Finally, there are items that just don’t date, even after many decades. They are as in style now as they were 50 years ago and look exactly the same today as they did back then. The public keeps buying them so there was no need to redesign. No need to fix something that wasn’t broken. These items are “iconic” because they are extremely recognizable, worn by a wide spectrum of age groups, and in many cases sported by both women and men. The original Dr. Martens lace up boot, Ray-Ban Wayfarers, Chuck Taylor Converse sneakers, Gucci loafers, the Chanel 2.55 handbag, studded diamond and pearl earrings are examples that spring to mind.

So things aren’t as simple as just investing in a so-called timeless item and leaving it at that. Even timeless items have an expiry date. The good news is that there are many classic, vintage, avant-garde and iconic items that will serve us for a very long time.  

The Melin ankle boot, or “bootie” is stunningly beautiful and made in Italy. It’s like a dressy jodhpur boot! Its masculine and feminine vibe is appealing, and the less than two inch heel even more appealing. It’s comfortable, although an extra cushioning insole can never hurt. I love the snug ankle fit, elastic insets, cracked patent finish, brogue detailing, and pull-on tab. It runs true to size and will probably not fit a wider foot. Available in burgundy and black. I hope to purchase these in black because the heel height, comfort level, dressy integrity and streamlined ankle fit is hard to come by in booties these days.

This perforated black belt by Style & Co is divine because the cut-outs look like you’re wearing a patterned belt. It works well threaded through the belt loops of trousers, shorts and jeans, and as a waist cinching belt on a dress. It’s that much more interesting than a plain black belt. Runs true to size and is lightweight. Its dressy integrity works well for career wear.

One way of adding interest to a neutral ensemble is by incorporating items that are texture-rich, like these booties and belt.

I like the pairing of cropped sweaters with skirts for four reasons. One, the proportions look fresh. Two, it’s a great way to de-bombshell a pencil skirt as well as dress it down when the sweater is boxy. Three, it’s so comfortable. And four, cropped knitwear brings back fond memories of fun ’80s fashion. 

The photos below show an assortment of cropped sweaters worn over skirts. Some of the knits are chunky and some fine gauge. Some are fitted and some boxy. Some necklines are high and some are low. 

I like all the variations, but have my favourites. I like the cropped chunky boxy fits best over pencil skirts, and the more streamlined cropped fits best over flared skirts. Although I don’t have this version covered in the photos, chunky-boxy versions work well over a flared skirt, both short and long, if the sweater is VERY cropped (like midriff baring cropped).

I just bought a form-fitting cropped, multi-coloured twinset in a fine gauge knit that I love to wear with wide leg trousers and flared skirts. It’s cropped to my waist and looks quite cheeky. To wear it with a pencil skirt works, but is not my favourite combination because it feels too “bombshell” for my style. Although the pairing is fab on those who like to wear body conscious outfits. 

You might have a cropped sweater lurking in your closet that doesn’t get much wear. Try it over a pencil or flared skirt just for fun. Or try on a cropped sweater in stores if you’d like to give the look a bash. Add in hose and footwear of your choice and you’re done. Who is going to try this combination?