The Room
99 Ossington Ave
Toronto, ON M6J 2Z3
Tue–Thu: 6pm–1am
Fri–Sat: 6pm–3am
Sun: 6pm–midnight
Mon: Closed
$$$ (Cocktails CAD $17–$22)
Late night, Date night, Industry crowd
Electronic and soul playlist, Occasional DJ sets
Smart casual to dressed up
Recommended weekends
PrettyUgly sits at the top of Ossington — the most cocktail-dense street in Toronto — and holds its position with 20 rotating cocktails built around seasonal ingredients and good storytelling. The name comes from the founders' belief that the best bars are a little rough around the edges. The room is narrow and dark, long oak bar, exposed brick. The aesthetic works because the drinks do.
On a Friday after 8pm the energy is relentless and you will likely stay later than planned. The Clarified Milk Punch is the current house signature — a drink that demands respect and attention. Browse our guide to Toronto's best cocktail bars for more refined drinking options across the city. The bartenders here see cocktails as a craft, not just a way to move bottles. Sister bar Reposado sits a few blocks south and operates in the same philosophy.
PrettyUgly works best when you arrive with an open mind about what's on the menu that night. The seasonal negroni variations are worth tracking across visits. If you're serious about cocktails and late-night energy, this is one of the best cocktail bars in Toronto. The industry crowd that works behind other bars often ends up here after their shifts, making Friday and Saturday nights especially animated with bartender talk.
The house signature. Complex, creamy, requires attention. Each sip reveals different layers of the technique that went into making it.
Mezcal, falernum, passion fruit. A balanced drink with real personality that showcases the bartender's understanding of tropical and smoke.
Whatever the menu says. The bartenders rotate ingredients seasonally — each iteration builds on classic structure with fresh thinking.
Ask what they're excited about that night. The best drinks often come from the bartender's current obsession, not the printed menu.
Friday evening from 8pm onwards for full energy and the best bartender conversation. If you want bar seats and more intimate talk, weekday evenings are your moment — you can actually hold a conversation with the person next to you.
Cocktail bar regulars who take drinks seriously. Late-night drinkers who want more than just a drink. The industry crowd after their shifts. Couples on date night who value craftsmanship. Anyone who believes the best nights start with a great cocktail.