holiday style survival guide | OUTVisions for LGBT Professionals

holiday style survival guide

get the look for holiday cocktails

holiday style survival guide
gavin reynolds

More often than not, I find myself struggling to put together the perfect holiday outfit at the very last minute. Luckily when in doubt, I have the benefit of being able to defer to some of Toronto’s most stylish tastemakers.

Along with the snow and sleigh bells, December usually brings with it an endless parade of parties and potlucks coupled with celebratory cocktails and countdowns. With so many social gatherings to celebrate, chances are you’ve already got your outfits styled and ready to roll, right?

One of the first fashion hurdles you’re sure to encounter this season is a good old fashioned cocktail party. Call me clueless but I for one have never fully understood the occasion and more specifically, what exactly constitutes ‘cocktail attire’. So before we can dress for success, we need to know exactly what we’re getting into.

The cocktail hour emerged in the roaring ‘20s as the fashionable transition from day to evening. Since then, it has continued to evolve and has taken shape in countless incarnations. The dress code calls for something more formal than your average day wear but also, slightly more relaxed than full black tie formal wear.

Today, we’re busier than ever and don’t always have the luxury of unwinding after a long day. As a result, the cocktail hour has been lost in the fast paced shuffle of everyday life as have our sartorial standards for such an occasion. 

Even by today’s somewhat relaxed attitude towards fashion, cocktail hour is an opportunity to impress your peers with an effortlessly chic look. For the gents, the key ingredients for cool cocktail attire include a well tailored look consisting of a great textured wool jacket or cashmere sweater over a crisp cotton dress shirt. Pair this with your favorite dark trousers and finish the look off with bold neckwear, sharp accessories and some fantastic footwear.

With a crash course in the cocktail soirée sorted, the annual company holiday bash is one event that requires a more strategic approach to partying. Mixing with the boss is challenging enough and when you throw a little alcohol and a good party into the mix, it can be a difficult landscape to navigate. The rule of thumb is to always wear what’s comfortable and what makes you feel confident. With that said, this is still a work event and it can be a great opportunity to stand out and assert your status as a leader and not a follower. Matthew Masciangelo is the CEO, lead designer and tailor behind Masciangelo Design Inc. This cutting edge Toronto clothier is best known for their high quality, custom bespoke handmade suits. “Keep it simple” says Matthew. “Opt for a nice subtle check or stripe over a bold pattern- too bold can look tacky.

Adding accessories ties the look together too. If the pattern is bold, go subtle and plain with accessories. If the pattern is plain, jazz it up with bolder patterned accessories”. It’s an opportunity to try out a trend that you might not normally consider for the office. Use your best judgment and just remember that a slight fashion faux pas isn’t likely to cost you that big promotion. Keep it appropriate but try something different that will let your star quality shine through. Ladies, avoid plunging necklines and skirts that are slightly too short. Instead, make a splash with a bit of festive sparkle or a statement necklace. Gentlemen, step it up! Ensure that your best shoes are polished, your outfit is pressed to perfection and finish it off with quality accessories such as a great leather belt an eye catching watch.

With great style sorted, good manners must follow suit for the holidays. Throughout the festive season, you’re sure to be stopping by the homes of friends, celebrating another great year with your coworkers and spending some much needed quality time with the family. The holidays are a fantastic opportunity to show someone how much they mean to you. Avoid the typical bottle of wine or box of chocolates. Instead, give something truly unique without breaking the bank. A fantastic candle can make the perfect gift for the host or hostess. If a book you read this year stands out as a personal favorite, why not pick up a copy for a friend? If you’re looking for a gift to impress the boss, “a pocket square is a small accessory that makes a huge difference in appearance. A custom pocket square means you can choose the perfect colours, patterns, textures, monogram etc” says Masciangelo. “It’s a great gift that’s totally personable depending on who you’ve got in mind”. No matter what you choose to give just don’t show up empty handed. It truly is the thought that counts.

When it comes to dressing to impress, the last party of the year is also the first opportunity to set the tone for what lies ahead. New Years Eve is the last big celebration so why not go out with a bang? The New Year is all about putting your best foot forward, so how can you achieve this through your own sense of style in 2015? Angela and Julie from Toronto’s famous Fitzroy Boutique know a thing or two about personal style. These ladies have taken their infectious sense of style and parlayed their creativity into the city’s trendiest pop up shop. Fitzroy travels to different neighborhoods all over Toronto throughout the year, in the style of the amazing London markets. “Personal style is about wearing what makes you feel good” they tell me. “It could be about expressing who you are or wearing that outfit that just makes you feel like a rock star. Either way it’s about confidence and feeling great”. How can you pull it off? “We think that combined with pieces that fit you properly and colours that work for your skin tone help to make the look work best for you. That being said, a new haircut or colour for the New Year can work wonders too. Right now we’re loving the LOB (long bob) cut!” Anything we need to leave behind in 2015? “Anything ombre! It’s a look we’re totally over”.

Be sure to check out Masciangelo at:

Shop Fitzroy Boutique online at:

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Authorgavin reynolds

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