Located in the heart of Richmond, amid the hustle and bustle of Swan Street, The Ugly Duckling is an upscale cocktail and wine bar that knows a thing or two about winter drinks and nibbles.

Opened until ‘late’ every night of the week (bar Monday), The Ugly Duckling is renowned for its bespoke cocktail menu, a healthy list of over 200 of the finest local and international spirits and liqueurs, and a dedicated wine list focussing especially on Victorian, Italian and European varietals.

Food-wise, there’s a selection of antipasto-style charcuterie and cheese platters, freshly shucked oysters and other delicious bites. The trees sprouting in the middle of the dining room and soft mood lighting make for an awesome winter date night venue.

Style suggestion
The Ugly Duckling is a little more upscale than your typical Richmond beer bar, so leave the ripped indigo jeans at home and try well-pressed tan chinos instead. Pair these with a button-up shirt, knit blazer and (if it’s a proper Melbourne winter night) a woollen overcoat. For shoes, a classic Chelsea like the HARLEY or LUCCA is spot on. You can also try a sharp Chukka, like the ADAMS or BRODY. Just remember to cuff those chinos.

Walking into Lagotto is refreshing break from the often grim Melbourne winter. Flack Studios is behind the design, and they’ve gone with an ‘Instagrammable’ terrazzo floor, curved booths, a long marble bar with red leather stools, and a steel island bench reminiscent of Italian espresso bars.

Located on the border of Carlton North and Fitzroy North, Lagotto is one of Melbourne’s newest “it” spots, focusing on fresh produce, award-winning cocktails and wines, and an environment that guests want to come back to.

Snack on the ultimate antipasto platter while sitting back with a negroni or old fashioned in hand, or try the charcuterie, which is both Italian and locally sourced. If ordering from the menu, the caponata (a Sicilian delicacy) is delicious.

Style suggestion
When the venue reads ‘fancy wine bar’, it’s a good idea to reach for your Chelsea boots. Our DEXTER Chelseas in khaki suede are the perfect match for Lagotto’s schmick marble and art deco aesthetic. Try them with cuffed, slim-fit jeans, a collared shirt and crew knit. At night, you can even consider dress shoes, although we wouldn’t recommend starchy black Oxfords for this one. Pick something with warmth and character, like our TOMMASI brown brogues, instead.

Photography: Kate Shanasy for Lagotto

When Bar Margaux opened in 2019, it quickly became Melbourne’s go-to, late-night eatery. Open seven days, this place just oozes charm and class. It practically leaks out of the walls. You’ll find Bar Margaux on the basement level at 111 Lonsdale Street. Just head down the nondescript stairs, open the door and you’re suddenly in 1920s Paris.

French comfort food is the go here, perfect for braving a cold Melbourne winter.
Try the MGX cheeseburger with bacon and its famous sauce, topped with frites. Or the 600g dry-aged sirloin on the bone for two. Wash it down with Bar Margaux’s extensive wine and cocktail list. We recommend sitting up at the bar, too. It definitely adds to the atmosphere.

Style suggestion
Bar Margaux is usually where you finish the night. It’s the spot for a nightcap and a cheeseburger you’ll remember all the way home in the Uber. For footwear, try something that will go from the pub, to the restaurant, to the underground 1920s French cocktail bar: maybe some UTAH brown ankle boots, or chunky-heeled PATTON Chelseas. You don’t need much to finish these off, just some indigo jeans, dark crew knit and a trucker jacket.

Photography: Jake Roden for Bar Margaux