Winter fashion can be hard to master. During the warmer months, a maxi dress, sandals and a pedicure equals instant dress-up. But finding a cute, non-itchy sweater that fits under a coat or discovering the perfect stylish and practical winter boot can be a challenge.

Luckily, we tracked down Janna Zittrer, Founder and Shopper-in-Chief of Montreal Shopping Tours (as one of the coldest cities in the country, we knew she'd be able to list a few items to make winter feel a little less painful).

Here are a few of her favourite finds (all local retailers from Montreal!).

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  • A Cute, Waterproof Bootie

    Finally a bootie that’s fierce enough to suit your fashion needs yet fit for winter -- thanks to its waterproof and slip-proof treaded sole. <em><a href="http://www.lacanadienneshoes.com/boots/heel/milanya-smoke-suede.html?___store=ca_english&___from_store=ca_english&countrySelection=ca_en" target="_hplink">La Canadienne Milanya, $325</a></em>

  • The Ultimate Mitt

    It doesn’t get more luxe than lambskin leather lined with soft rabbit fur. <em><a href="http://www.rudsakstore.com/lambskin-leather-mitten-p400/" target="_hplink">Rudsak Glory Mitten, $90</a></em>

  • Get Down With Down

    A slim cut and longer silhouette make it possible to look polished even in a puffier jacket. <em><a href="http://www.mackage.com/ca_en/shop-online/women/newarrivals/kay-b" target="_hplink">Mackage Kay-B, $680</a></em>

  • A Nice Boot

    A tall winter boot will keep your feet dry whether you’re kicking back on the weekend or climbing over snow banks on your way to work. <em><a href="http://www.aldoshoes.com/ca-eng/women/boots/cold-weather-boots/91308229-bossi/95" target="_hplink">ALDO Bossi boot, $110</a></em>

  • The Weekend Bag

    You can’t get much more Canadian than a hockey bag, and this particular tote puts a stylish spin on the standard nylon styles. <em><a href="http://www.m0851.com/webstore/index.php?pid=BALHO04&lang=ENG" target="_hplink">M0851 Hockey Bag, $480</a></em>

  • A Warm Noggin

    Crafted from reclaimed leather and fur, this hat will keep your head warm without horrid hat head. <em><a href="http://www.harricana.qc.ca/boutique/index.php/french/sila-aviator-black-recycled-leather-sheared-black-2.html" target="_hplink">Harricana par Mariouche Sila Aviator hat, $269</a></em>

  • Cozy Cashmere

    For when you want nothing more than to swathe yourself in cozy knits, this cashmere shawl does just the trick. <a href="http://shop.lolaandemily.com/products/copy-of-copy-of-copy-of-copy-of-copy-of-ca-va-de-soi" target="_hplink">Cleo Scarf-Shawl by ça va de soi , $350</a>

  • Bum-Covering Coat

    This is Andy Thê-Anh’s first collection for the activewear brand, and the Montreal-based designer’s attention to detail is already helping to raise the bar on sportif style. Case in point: this ski jacket with Art Deco–esque geometric stitching. <em><a href="http://www.lolewomen.com/luw0118.html#images" target="_hplink">Lolë Gisele jacket, $240</a></em>

A Cute, Waterproof Bootie
Finally a bootie that’s fierce enough to suit your fashion needs yet fit for winter -- thanks to its waterproof and slip-proof treaded sole.
La Canadienne Milanya, $325

The Ultimate Mitt
It doesn’t get more luxe than lambskin leather lined with soft rabbit fur.
Rudsak Glory Mitten, $90

Get Down With Down
A slim cut and longer silhouette make it possible to look polished even in a puffier jacket.
Mackage Kay-B, $680

A Nice Boot
A tall winter boot will keep your feet dry whether you’re kicking back on the weekend or climbing over snow banks on your way to work.
ALDO Bossi boot, $110

The Weekend Bag
You can’t get much more Canadian than a hockey bag, and this particular tote puts a stylish spin on the standard nylon styles.
M0851 Hockey Bag, $480

A Warm Noggin
Crafted from reclaimed leather and fur, this hat will keep your head warm without horrid hat head.
Harricana par Mariouche Sila Aviator hat, $269

Cozy Cashmere
For when you want nothing more than to swathe yourself in cozy knits, this cashmere shawl does just the trick.
Cleo Scarf-Shawl by ça va de soi , $350

Bum-Covering Coat
This is Andy Thê-Anh’s first collection for the activewear brand, and the Montreal-based designer’s attention to detail is already helping to raise the bar on sportif style. Case in point: this ski jacket with Art Deco–esque geometric stitching.
Lolë Gisele jacket, $240