The thing about the work-life boundary becoming more seamless is the one-look-fits-all wardrobe that inevitably follows. It’s easier (and infinitely more stylish) than it sounds: the trick to
dressing for the office and events afterward is shopping smart, and investing in essentials, while swapping in key pieces each season for personality.

“It doesn’t have to be complicated any more,” says Erin Swan, owner of
Charlie Boutique in Toronto. “You don’t have to lug your sequined party dress to the office.” We rounded up Swan’s top 10 never-fail fashion rules for transitional dressing from day to night.

Transitional dressing fashion rule #1: Invest in key pieces

A foundation of great essentials will make it easier to swap in more colourful, on-trend pieces each season. “Strongly build good bones with a wardrobe that’s easy to transition from day to night,” says Swan. “And there are key pieces to make transitioning easy.” Swan suggests creating a “kit” with five great pieces (as follows) that can seamlessly take you from office to whatever after-hours event you’re headed to next.

Transitional dressing fashion rule #2: Own a great LBD

We couldn’t agree more—a classic little black dress has never let us down. “It’s by far the easiest piece to transition to night,” adds Swan. She’s a big fan of Montreal designer’s Valerie Dumaine’s sleek, well-fitted dresses for the occasion.

FASHION RULES: 5 ways to wear your LBD

Transitional dressing fashion rule #3: Get the perfect pencil skirt

These aren’t your boring office day outfits—the slim, knee-length skirts in patterned or metallic prints seen at
Prada and Marc Jacobs’ Fall 2013 runways were reminiscent of Hitchcockian heroines. And who wouldn’t want to look like they stepped out of 1940s cinema and into the boardroom—or a date night?

“It’s easy to make the transition without having two separate wardrobes,” says Swan, who loves Montreal designer Eve Gravel for a fitted pencil skirt.

Transitional dressing fashion rule #4: The silk blouse—own it

This pairs perfectly under a crisp blazer or
leather jacket (depending on the environment). “It’s an easy, key basic,” says Swan. “And once you have those down, you can add in personal style with accessories.” Try an airy, printed blouse from Toronto-based label Dagg & Stacey, and simply replace a classic gold watch with a stack of bracelets before heading to an after-work soirée.


 6 more fashion rules to stylishly upgrade your office wardrobe at night…

transitionrulescanvas.jpgTransitional dressing fashion rule #5: Work in a well-fitted pant
Perfect for pairing with the above-noted silk blouse, the well-fitted pant works great in a skinny cigarette style or as a wide-leg trouser for day and night. Pair a cobalt blouse with a classic linen pant by made-in-Canada label Birds of North America. “Then just add a sleek choker,” says Swan.

Transitional dressing fashion rule #6: Have a crisp white blouse on hand

The button-up white blouse can be worn with a pair of light denim pants and ballet flats in a casual office setting. “It’s as simple as adding on to it to change it up at night,” says Swan, who suggests adding in a colourful statement necklace and great pair of pointy-toed pumps.

Transitional dressing fashion rule #7: Stash statement heels at your desk

“I’m a big believer in kicking off flats and changing into an aggressive heel at night,” says Swan. Try a vibrant colour, spike heel, cool cutout or metallic shade to add personal flair.

GALLERY: 30 HEELS to lust over

Transitional dressing fashion rule #8: Embrace a fun clutch
Swapping out a tote or day bag for a hand-held equivalent is key to pulling together a polished look (plus it’s an excuse to leave the laptop at the office, friends). “Add a clutch in a beaded, daring colour,” she says. Or try an oversized envelope clutch.

Transitional dressing fashion rule #9: Add a topper

We’re all about the cute work cardigan for the office, but switch into a fun topper at night. “Try a leather or faux-leather moto jacket to add adventure to any outfit,” says Swan. Take your cues from Philip Lim 3.1 and Jean Paul Gaultier’s Fall 2013 runways for badass takes on the biker jacket. Or go for a classic tux-style blazer in a great print or vibrant colour.


Transitional dressing fashion rule #10: Use accessories to inject personality
The easiest way to take your outfit from day to night? “Add some jewellery and a red lip stain,” says Swan. Try a sparkly collar necklace or an arm full of layered bangles. “Scarves are a great option,” she adds, citing the prevalence of colourful silk headwraps this summer. But Swan can’t stress the transformative sartorial power of a great necklace or ear cuff enough. “Statement jewellery will pump up any outfit.”

Read more:
10 ways to upgrade your summer office wardrobe

What to wear to an internship
Top 10 Canadian fashion designers

Dressing for work: How to wear cobalt blue in the office