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2. Tote Bag

Sitting at the mid-point between a briefcase and a backpack on the sliding scale of formality, the tote bag is roomy enough to stow your smelly gym gear / stolen hard drive, but sleek enough that you might still get papped by a roving street style photographer. A versatile, easy-access design, this can be your beach bag, work bag and shopping bag all in one. Sadly, it’s also the only style on this list vulnerable to a “nice man purse” from at least one of your friends.

Materials, first and foremost. If you’re using it as your work bag, stick with leather and nylon. If all you want to do is rep your favorite brand while you do your shopping, then canvas is just fine.

A zipper at the top offers extra security, while internal pockets ensure you don’t have to go burrowing for your keys. Don’t discount a set of shoulder straps either: with the classic shopper style, you’re never fully hands-free.

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3. Weekend Bag

You can’t roll up to your rented chateau without an obscenely good weekender stowed in the limited boot space of your Jaguar F-Type. Whatever your travel plans, a weekend man bag suggests a man of taste and leisure, not to mention practicality when it comes to packing enough underwear. Perfect for stowing a neat capsule wardrobe and travel essentials, it doesn’t have to live under the bed between trips. At the smaller end of the scale, a duffel or holdall can be used every day as a hybrid work and gym bag.

You’ll find affordable leather options for not much more than $100, but you can spend ten times that figure from designer labels that specialize in leather goods. In the spirit of matching leathers, look for one that matches the shoes or boots you wear most often.

Check the dimensions if you ever intend to use it as hand luggage and if your weekends involve a little more rough and tumble than champagne and caviar, opt for a twill or canvas version from a hardy outdoor brand.