The best outfits always start from the ground up, and few foundations hit quite like a great loafer. Polished but never predictable, they’re the kind of shoe that instantly sharpens whatever you’re wearing, no effort, all impact. For this edition of FLANNELS 3-Ways, we’re taking one hero pair: the Saint Laurent Cassandre 'Le Supple' penny loafers. And pushing them beyond the obvious.

Think elevated everyday, directional layering and that perfect balance between dressed-up and off-duty. From early starts to late finishes, these are the looks that carry you through it all, with style to spare. Because if you’re investing in one pair, they should work overtime.

The easiest way to romanticise the 9–5? Show up like it’s your runway. This is workwear, but reworked: sharper, cooler, and a little bit undone in all the right ways.

 Start with a crisp Maison Margiela Oxford shirt, clean and classic, then dial it up with a Burberry check tie for that subtle heritage flex. Layer in the Maison Margiela broken gauge knit; slightly slouchy, textured, and just rebellious enough to stop things feeling too corporate. It’s that mix of structure and softness that makes the whole look feel effortless rather than overthought.

 Down below, tailored trousers keep everything streamlined, but the real power move? The Saint Laurent penny loafers. Sleek, understated, and quietly confident, they ground the outfit without stealing the spotlight. It’s giving “I have a 9am meeting, but I also have better plans later.” And honestly, that’s the energy we’re taking into every weekday.

When the city starts to warm up, your wardrobe should follow suit: lighter, brighter, but still pulling its weight. This is how you do spring dressing without losing your edge.

 Start with the Casablanca striped polo: playful, polished, and just the right amount of retro. It brings that easy, sun-on-your-face energy, while still looking considered enough for wherever the day takes you. Layer over a Gucci suede bomber jacket soft, structured, it’s the kind of piece that instantly elevates even the most laid-back look.

Acne Studios’ trompe-l’oeil jeans keep things interesting, blending classic denim with a slightly offbeat twist (because basics are overrated). Then come the finishing touches: Rick Owens oval sunglasses for that low-key, don’t-talk-to-me cool, and of course, the loafers. Still doing the most, without trying too hard. It’s giving coffee run turned spontaneous dinner plans. Effortless, elevated, and exactly how city style should feel.

After dark, it’s all about mood. Sleek, understated, and just a little bit dangerous. The kind of look that doesn’t ask for attention, it just gets it. A black leather jacket is your starting point, and this Dolce & Gabbana version brings that instant, wear-anywhere attitude. Throw it over a Tom Ford fine-knit V-neck and suddenly things feel sharper, more refined: clean lines, luxe texture, no unnecessary fuss.

Tailoring keeps it grounded. MM6 Maison Margiela’s straight-leg trousers add structure without feeling stiff, giving you that easy, elongated silhouette that works from bar to late-night wander. Accessories? Keep them intentional. A Montblanc watch adds a quiet flash of polish, while the loafers do what they do best, anchoring the entire look with timeless ease. It’s controlled, confident, and just a little bit indulgent. The kind of outfit that carries you from “just one drink” to suddenly it’s 2am and you’re still out.