The True Longevity of Timeless Items

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.  

Fab Finds: Brogue Booties and Perforated Belt

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.

Affiliates
Some of the links in this post generate commissions for YLF.

How to Wear Cropped Sweaters With Skirts

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?

Affiliates
Some of the links in this post generate commissions for YLF.
Roundups

Simpler Items

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

Read More

Assorted Items

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

Read More

Casual Summer Vibes

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

Read More

Summery Earth Tones

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

Read More

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

Your Favourite Animal Print

I’m mixing things up in this week’s poll by giving you a choice of several Teams. But you can still only pick one of them. You are sitting this one out on the bench with pumpkin loaf and hot chocolate if you can’t pick a side, or if none of the teams are appealing. 

Please select your favourite animal print, whether it’s in the form of clothing, footwear or accessories. Here are your options:

  1. Cat Prints 
  2. Zebra Prints
  3. Snake Skin Prints
  4. Giraffe Prints 
  5. Pony Prints

I have cat, zebra, snake skin and giraffe prints represented in my wardrobe. Cat prints, both cheetah, leopard and variations of them, are the most represented. But snake skin has my heart because I like that type of animal print best. I am on Team Snake Skin Prints. 

Over to you. Which Animal Print Team are you batting for?

3 Years In: Booties and Shooties with Visible Legs

To recap, a bootie is any style of ankle boot. Some styles extend a few inches above the ankle bone, whereas others just cover it. A shootie is a hybrid between a shoe and a bootie. Think of it as either a very short bootie or a very high vamped shoe. My low heeled black and white oxfords are essentially shooties with laces, and my animal print ankle boots are booties. 

Booties and shooties, in both dressy and casual incarnations, have been THE item of footwear in fashion for three years. And after following the Spring 2013 shows, booties and shooties are bigger than ever for a warm weather season. I could scarcely believe the popularity of this “closed shoe style” for Spring and Summer. The peep-toe variety was especially prevalent. 

Wearing booties and shooties with regular length trousers and jeans is a natural pairing because of the continuos, elongating vertical line that is created from leg to toe. But these days all outfits can be worn with some sort of bootie or shootie, which means dresses, short shorts, long shorts, rompers and skirts too. It’s thought of as a very modern footwear pairing and a lot more on trend than its low vamped cousins.

In 2009 I suggested guidelines on how to wear booties with skirts and dresses because it’s easy to feel dumpy, stumpy, frumpy and short legged when pairing high vamped footwear with visible legs. First, it’s a question of whether you like the combination of high vamped footwear on a bare leg, or hosiery covered leg to begin with. Then it’s a question of finding the right style of booties or shooties. Heel height, vamp height, ankle fit, and colour contrast become important factors to consider when wearing booties and shooties with skirts, dresses, cropped pants and shorts. Some prefer the fit of a streamlined bootie, whereas others like them to fit wider around the ankle. Some like taller booties, while others prefer shooties. Some like them flat and casual, while others like them heeled and dressy. Some prefer light colours, while others prefer black. Some will only wear booties and shooties with low colour contrasting hosiery, while others are happy to leave off the hose. 

For my own style, I prefer to wear low heeled booties with a very streamlined ankle fit when wearing them in outfits with visible legs. Sometimes barelegged and sometimes with hose. Better yet, I actually prefer to wear shooties because it’s easier to find a snug fit around the ankle. I have small bony ankles, narrow calves and a dainty frame. Oversized booties that are cut wide at the opening don’t work well for me, while they work flawlessly on others. In fact, I have clients with larger ankles and calves who much prefer wearing booties that are cut wider at the ankle because it makes their ankles look smaller, and balances out the shape of their calf. 

Furthermore, I have a small head and very short hair. To my eye, a voluminous hairstyle will often help balance out the “flower stem in a plant pot” effect that is created when you wear booties with wide openings. There is no hope of creating this balance with my pixie. 

So ladies, after three years of the fashion industry encouraging the look of which there is no end in sight, how do you feel about pairing booties and shooties with visible legs? Did you get used to the pairing over time, to the point that it now feels “normal”? Did you love the combination from the word go? Or do you not wear the look at all because low vamped footwear always looks better to your eye.

Affiliates
Some of the links in this post generate commissions for YLF.