Simple Holiday Dressing at Any Age

Fashion Style Thursdays holiday wear clothing It’s party season and that means party clothes, but finding the perfect holiday outfit can be a challenge.  The purse strings are already stretched so splurging on a one-time-only wear is not ideal, but settling for cheaply made and ill-fitting, well, this doesn’t flatter anyone over the age of 20.  I first discovered Thursdays, a boutique in Toronto’s posh Rosedale neighbourhood offering unique wardrobe staples at reasonable prices, through their Instagram account.  Their pictures offer inspiration for attainable fashion and with that, I knew that I needed to check out the store for myself.

The team at Thursdays, a range of women from their mid-20s to mid-50s, are passionate about simple style.  The vibe at the store exudes casual cool; basics are displayed in neutral colour palates ideally fitting in with any existing wardrobe and the occasional pop of colour or fringe adds some whimsy to an otherwise classic collection of clothing.

I asked Thursdays to style five different women, ranging in age, for various holiday fetes.  Store Manager Sam pulled together looks with pieces that will remain favourite staples in your closet long after the holidays have passed.  For more styling tips and images from Thursdays sign up for Plenty More, our monthly newsletter, and receive this bonus content!

Girls Gift Exchange Party Night

First up is my sister-in-law and new mom Aly of the blog Aly in Motherland.  I owe her a big thank you for being the first to model.  We all agreed that models get a bad rep, and that posing without looking absolutely ridiculous is much harder than it looks.   The brand of jeans that Aly is wearing are a favourite of hers and mine.  The slightly higher waist and skinny leg are both flattering and comfortable and they are available in a variety of washes and styles.

Girls Night Gift Exchange outfit from Thursdays

Hem skinny denim – $150

Off the shoulder blouse – $110

Holiday Brunch with Friends

My mom will do anything for me, including modelling an outfit.  Here she is making her Plenty debut, representing the glam-mas of the world wearing a casual, yet pulled together outfit that can take you from a brunch with friends to holiday matinee.

Holiday Dressing Brunch with Friends

Holiday Dressing Brunch with Friends

Knit tunic – $120

Faux leather jacket – $240

Suede legging – $120

Woven scarf – $80

Pop, Fizz, Clink, Cocktail Time!

I am so grateful that fashion blogger Mandy of Sparkle Shiny Love accepted the invitation to join us – she’s clearly the professional.  If you’re not already following Mandy on Instagram, you should – it’s chock-full of all things sparkly, shiny and lovely.  Mandy is wearing the “it” dress of the season that can easily be dressed up with glittery accessories and heels for a more formal occasion or dressed down with opaque tights and boots for a more casual look.

Simple Holiday Dressing Cocktails

Simple Holiday Dressing Cocktails

Simple Holiday Dressing Cocktails

Moto jacket – $260

Mock neck, long sleeve swing dress – $160

Straight From The Office

Carol is absolutely stunning and she has no idea – and that’s one of the many reasons that I love her. Her heart is just as beautiful because she’s game to make a fool of herself in a laneway and allow me to take pictures of her.  She’s wearing an outfit that can easily go from the office to the office party. It’s a blank canvas where one could add layered necklaces, or oversized bracelets for a more festive look, but I think Carol nails the more demure look.

Simple Holiday Dressing Office Party

Simple Holiday Dressing Office Party

Pink wool coat – $225

Culottes – $125

Collarless moto jacket – $250

Crop T-neck longsleeve – $98

Holiday Glam

And here’s me.  I still cringe thinking about the “modelling” session but it was a lot of fun to play dress-up with this group of ladies.  I am showing off a more traditional holiday party look but each of the pieces can be re-worn in a variety of different ways.  Sam and the women from Thursdays are great about coaching those of us who can’t figure it out on our own.

Glamourous Holiday Party look from Thursdays

Glamourous Holiday Party look from Thursdays

Knot Neck dress – $100

Fur vest – $320

For more exclusive styling tips sign-up for our monthly newsletter, Plenty More, on the right side of the home page.

Disclosure: Plenty was not paid a cent for writing this article . . . in fact, this outing ended up costing us money!  I couldn’t let those culottes go. All pieces can be purchased at Thursdays and they do receive telephone orders.  

PS. Once you’re finished dressing and are ready to shop, check out our gift guide at – lots of ideas and deals!

8 thoughts

  1. You ladies look fantastic. Thank you for your kind words – it was an absolute pleasure working with you! Hope to see you soon!

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