Stylists and image consultants often swear by the fact that you’ll lengthen your legs by wearing the same colour shoes and legwear. While I agree with this style tip, as a strict rule it can get boring, especially if your daily dress is business casual. Contrasting the colour of your footwear with your pants or jeans is striking and makes an outfit pop.

I believe that lengthening your legs has more to do with the fit and length of your pants, and the style of your shoes. If your pants are bootcut, flared or wide (not skinny), and they skim the surface of the ground when you wear heels, you’ll achieve that long lean vertical line despite the colour of your shoes. And pointy toed peds will elongate this line even further .

By all means sport an alternative colour shoe to your legwear if you fancy that idea. You don’t need to have long slim gams to pull off the look if you adhere to other important leg-lengthening rules. Adding contrasting and eye-catching shoes to a classic ensemble is a perfect way to keep your look hip when current trends aren’t your cup of tea.

We’ve just got back from five fabulous days in Chicago where friends of ours got married beneath the stars at the Adler Planetarium. Magical wedding moments, delectable food, splendid architecture and spectacular shopping made for a great getaway and we enjoyed every moment.

The Magnificent Mile is Chicago’s most fashionable street and the place to be if you have shopping time to spare. The ultra wide boulevard is lined with exclusive designer shops like Burberry, Salvatore Ferragamo and Gucci that stand side by side more affordable chain stores like Guess, Mango, French Connection, Eddie Bauer, Ann Taylor, Banana Republic and the Gap. Department stores like Saks, Neiman Marcus and Nordstrom were beautiful and well worth a browse (schedule and pocket permitting).

I had my favourites amongst the overwhelming choice of retailers along the Mile:

• The brand new 3-story-high Hugo Boss store was a highlight. I’m a true Boss fan when it comes to a modern, understated and perfectly tailored look for gents and the shopping experience here was sublime.
• French Canadian store Carriere specializes in unique career wear suiting and I loved the finish of these garments. Classic button down shirts and jackets with insanely funky design detailing tickled my fancy.
• With their keen prices, good old H&M seldom disappoints and remains the best place to get a cheap fashion fix.

Off the Mile along State Street is the most lavish Macy’s I’ve ever seen. Originally a Chicago department store called Marshall Field’s, the store takes up the entire block and reminds me of world renown Parisian department store Galleries Lafayette. The stores most unexpected interior feature is it’s pretty Tiffany Mosaic Dome. There is also an adorable doggie section that boasts a range of elaborate doggie day beds, one of which we nearly flew home with us.

My impression of Chicago is a positive one. Hot and humid weather conditions made dresses, city walk shorts, swing tops and peep-toed shoes an urban uniform amongst locals. Dress codes sizzled at night as glitzy, alluring mini dresses matched with the highest of heels became standard evening attire. I saw a high style quotient in the short time that I was there and enjoyed taking in the view.

The Magnificent Mile.

Having a sense of style is somehow a mixture of looking both timeless and “of-the-moment”. While choosing to remain classic is stylish, you’ll need to incorporate a certain level of “right-now” into your look to keep it current and fab. So what do you do when you don’t like, or can’t afford, the new trends?

Here’s how to keep it in vogue when you bypass trends:

• Stick to tailored items. The watershed changes in fashion silhouettes over the last year are not for everyone (or at least, not until our eyes have adapted to the changes). Ignore the voluminous look and stick to clothing that skims the contour of your body because chic tailoring is universally flattering and always fashionable.
• Integrate the new fashion colour. If you love cobalt blue, but can’t see yourself wearing trapeze jackets, sack dresses and swing tops, try it as an accessory or in a classic clothing piece instead. Camisoles, button down shirts, layering knit tops and costume jewelry are safe and inexpensive ways of packing the right amount of punch per season.
• Add the “it” style of jeans. This boils down to either skinnies, straight-leg cuts or wide-leg cuts this season. Choose what’s best for your body type and modify your look.
• Invest in a great pair of shoes. You’ll always make a stylish statement with a wonderful pair of peds. Dressing well is about getting the details right and this detail is particularly important.
• Buy the bag of the season. You won’t go wrong with patent and it won’t cost you an arm and a leg. You can get a perfectly great option for $50 at places like Aldo, Gap, Macy’s and the BP department at Nordstrom.
• Try a new hairstyle. Add an edge with a new cut or spot of colour.
• Change your specs. If you wear glasses, make sure that they are the best pair that you can afford. I can’t stress enough how important this is. The eye is drawn upwards when we speak and nothing is more effective than a pair of perfectly eye-catching specs. Leave the clothes and invest in the most important accessory that you own.
• Try a new shade of lipstick. If you normally go neutral, try a brick red, magenta or bronze instead.

Actress Jennifer Aniston epitomizes the stylish modern classic. While she’s probably never stuck for cash, she’s chosen to keep her look tailored, simple, current and neutral. She’ll update seasonally with the most current pair of jeans, white shirt, black pants, black shoes, new handbag, sunglasses and a variation on the hairstyle. She usually leaves it at that and always looks fab. Sometimes you won’t like the new trend, and sometimes it won’t like you. Either way, it’s possible to look hip by choosing the correct items in a given season.

Jewel toned sapphire patent tote, teal ballet flats and dark straight-leg jeans are an inexpensive and modern classic combo from the Gap that will have you looking hip straight way. These items are also offered in neutral shades if that’s your preference.

Lounging sweats are everywhere, but it’s not easy to find ones that are flattering, fun and hold up well in the wash. I am particularly fussy with loungewear because I will not settle for anything that’s drab, ill-fitting and badly made (remember ladies that we lounge with style). While fab yoga and athletic gear will also work, they’re not my choice for superb stay-at-home comfort.  I prefer baggy, wide-legged, ultra soft, 100% cotton terry cloth as opposed to anything remotely clingy and synthetic. Satisfying my comfort criteria is a tall order when you still want to feel attractive in your sweats.

This season, Victoria’s Secret did the trick with their “loungey, lazy and fit-tastic” sweatpants and hoodie-top options. The pants are low-ish in the rise but wide, long and luxurious all the same (good for those with long legs). If long sweats are too warm for your climate, try the shorts option instead. I have those too and highly recommend them. The hoodie-tops are loose yet tailored and the perfect length. These sweats come in an assortment of colours (e.g. navy, grey and yellow), so don’t be put off by the pink if that’s not your cup of tea. Think beyond buying  a matching set of sweats and mix up the colours a little for a more edgy ensemble.

I would never have thought to look for my loungewear at Victoria’s Secret, which just goes to show that you should never rule out a retailer. I’m delighted with my new sets of sweats and wear them every day.

Fit-tastic, loungey sweats from Victoria’s Secret.