The Annex Bag draws from one of Toronto’s most storied neighbourhoods. Leafy, cultured, and effortlessly cool, the Annex is where historic architecture meets creative energy. Structured yet effortless.
We partnered with Toronto-based stylist Shira, who calls the Annex home, to style the bag through the lens of city life. With work featured in Harper’s Bazaar, Paper Magazine, Cultured Mag, and Elle Canada, Shira is known for editorial shoots, celebrity styling and ad campaigns that balance artistic innovation with enduring style. Shira’s creativity comes through in looks that feel unexpected yet timeless. Her approach is always grounded in real life and reads relevant, considered, and wearable.
We asked Shira to share her perspective on the east–west bag silhouette, styling a more directional bag, and how city life shapes the way she dresses.
On the East–West Shape
“Spring is about moving freely,” Shira explains. “The east–west silhouette feels elegant but easy-going. It tucks comfortably under your arm or swung across your body when you’re on the go. The silhouette feels lighter and more fluid compared to the larger vertical shapes we’ve been seeing in the colder months.”
The Annex Bag embraces that shift — refined, streamlined, and designed to move with you.
On Styling a Directional Bag
“For me, it always comes down to balance. If a bag feels bold or more directional, I like to ground it with simpler, timeless pieces so it has room to stand out.”
Three ways to ground a statement bag:
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Classic: Pair it with classic wardrobe shapes
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Monochrome: Keep the colour story tight with tonal neutrals
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Bold: Layer a textured bag on something bold but intentional
Look 1: For the Classic Dresser
Products: The Annex Bag Black, The BLVD Mary Jane Black
Shira offers this styling advice: “Stick with a classic, minimal base and let the bag do the talking. Even with a minimal style, a directional bag is an easy way to add personality to your look without compromising your aesthetic or stepping too far out of your comfort zone.”
The Style Formula:
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A blazer adds structure up top
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Relaxed denim balances the sharper lines of the blazer and bag
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A directional bag and complementing flats make the look feel styled, not simple
Look 2: For the Monochromatic Dresser
Products: The Annex Bag Clay Nubuck, The Claire Slingback Taupe Snake
Shira suggests, “Pair it with neutral pieces or a monochromatic outfit so it feels intentional, not overwhelming.” Playing with tone and texture breathes life into a monochromatic look.
The Style Formula:
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Neutral, tonal layers feel thoughtful and elevated
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Mixed textures like silk, suede, or cashmere add interest
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Pointed flats add polish. Optional: pair animal print as a neutral
Look 3: For the Bold Dresser
Products: The Annex Bag Desert Snake, The BLVD Mary Jane Black, The Toujours Tall Boot Black
According to Shira, “The goal is for it to feel intentional, not overwhelming. I like to pay attention to texture, proportion, and colour so the look still feels easy and wearable.” Animal print works best when the rest of the outfit feels grounded. But this doesn’t mean you can’t go bold.
The Style Formula:
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Black leather coat and flats for structure and impact
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Use white or an interesting fabric, like silk, on bottom a compelling contrast
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The animal print bag is your statement piece
On City Life and Function
“As someone who lives in the Annex and thrives on city life, function always plays a role in how I dress. I gravitate toward accessories that can move with me through a full day—walking my dog, fittings, meetings, errands, without feeling too precious. The pieces I reach for most balance practicality with style, so they look sleek and feel functional".
“I like the balance of feeling put-together and also at ease, and a carefully chosen accessory like the Annex Bag not only elevates a simple look but is also functional enough to keep up with my busy day.”
The Annex Bag was designed for exactly that. Keeping pace with a busy day. Structured. Effortless. Ready for wherever the day goes.
