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We thoroughly research all the products we feature, and we honestly think they’re great. But just so you know, things you buy from links on this page may earn us a commission. All prices were accurate at publish time.

We all love that signature piece – the handbag. It can be the difference between a look fit for a glamorous evening out, or just a casual, slouchy weekend getaway. With a few choice pieces in a variety of textures, sizes, styles, and shapes, these bag selections are versatile, stylish, practical and, best of all, can transform your regular ol’ outfit into the outfit.

1. Vintage-style pleather tote bag

We can surely all agree – no handbag collection is complete without the staple that is a practical and stylish tote bag. And this vintage-style piece not only looks classic, it’ll go with almost anything – from your formal work threads, to your weekend athleisure, to your most glamourous evening wear. If you don’t have one, it’s sure to fill a gap in your forever wardrobe, and this one’ll look dreamy with a smart double-breasted burgundy coat, block heel boots and cropped denim.

Large vintage-style pleather tote bag, $36 at Amazon.

Amazon, The Bay

Amazon, The Bay

2. The one with many compartments

There’s nothing quite like a big ol’ spacious bag that holds everything. Especially if it’s in a gorgeous scratch resistant leather. Canadian designer Voylan sources their materials from the finest family run Italian workshops, meaning you are getting luxury quality bags at a lower price point. The best part? This bag has got compartments galore, so you’re not just throwing your things into giant handbag abyss. At $450, it’s not exactly a bargain but compared to its luxury $1000+ counterparts, it’s value for money.

Voylan Montreal Hobo, $450 at Voylan.

Voylan, The Bay

3. A sleek envelope clutch

A smart envelope clutch may be one of the most versatile, underrated handbag options. It’s the perfect accessory for a wedding, dinner, or even a smart lunch meeting. And with this simple black number, we’d opt for a sharp pair of mustard heels, an ivory Bardot top, and sophisticated cigarette pants.

Envelope clutch, $22 at Amazon.

4. A versatile leather backpack

A traditional handbag is great, but for practicality (and even weight distribution), a backpack is sometimes the only way to go. But that doesn’t mean you’re stuck with a look reminiscent of your high school days, oh no. With this stylish leather knapsack, you don’t have to compromise an inch on style, and you can still fit in all your essentials for the day. It also comes in 14 colours, so you’re spoiled for choice. Throw on a long printed cardigan over jeans for a cozy, effortless look.

BOYATU Genuine Leather Backpack, $93 at Amazon.

Amazon, The Bay

5. A classic vegan leather carry-all

The problem with faux leather is that it doesn’t always feel as luxe as the real thing. Not with Canadian Korean family owned brand Ai. Their Park bag comes in six sleek colours and is as elegant, classic, chic and buttery as any leather handbag. With its clean lines and timeless shape, this piece feels just as at home with a pair of sweats as it does with an LBD. Bonus: it comes with a pouch.

Ai Park Bag, $150 at Ai Toronto Seoul.

Ai, The Bay

6. The convenient belt bag

We know not everyone is ready to hop aboard the fanny pack train, but hear us out. A chic looking belt bag with all the compartments just might be the most practical investment to your wardrobe this year. Stick the straps through your belt loops and relish in the freedom of feeling purseless. Not sold? Okay, fine, wear it as a crossbody on your next grocery run.

Loulou belt bag, $89 at Poppy & Peonies.

Poppy & Peonies, The Bay

7. A spicy snakeskin neutral

When you want your neutrals to pack a little punch, snakeskin is always a good option.  With its boxy shape and gold hardware, this piece looks way more expensive than it actually is. Throw this fashionable little bag over a monochrome dress and a blazer and call it a day.

Qirassi crossbody bag, $55 at Aldo.

Aldo, The Bay