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Step into September with Attitude’s autumn style guide

From fuss-free tailoring to the season’s must-have shoe, autumn dressing calls for considered classics.

By Joshua Graham

A new month and a new season promise fresh beginnings, so what better time for a wardrobe refresh? Our September style guide is here to make getting autumn ready easier than ever.

Because let’s be honest – September can feel like the Monday of months. To-do lists get longer, calendars fill up, and suddenly summer’s easy, breezy days are a distant memory. The key to escaping the transitional season rut? Pull yourself together with timeless silhouettes and versatile layering. The right pieces make mornings quicker, decisions easier, and days a little less chaotic. Call it fashion with benefits: smart, versatile staples that work as hard as you do.

Osprey ‘The Carter holdall’ 

Osprey 'The Carter' holdall leather bag in chestnut
Osprey ‘The Carter’ holdall (Image: Provided)

A master of leather since 1980, Osprey has perfected the art of blending craftsmanship with style. Enter The Carter: the holdall that does it all. Durable enough to take anywhere, refined enough to take everywhere. With its adjustable strap and classic silhouette, it moves seamlessly from boardroom to weekend break, proving that true style never clocks off. Generously sized yet effortlessly elegant, it’s the kind of bag that only gets better with age – because timeless should mean just that.

Sloggi SLG Base trunks

Sloggi SLG base trunks twinset in black and blue
Sloggi SLG Base trunks (Image: Provided)

Because there’s no better time than the present to upgrade your underwear game, meet the SLG Base trunks. Crafted from ultra-soft organic cotton, these short-style briefs prove that essentials don’t have to be ordinary. Think clean lines, a sleek hand feel, and a waistband so soft you’ll forget it’s there – until the subtle branding reminds you it’s smarter than your average pair. Sustainably made, stylishly designed, and packed in twos, because one is never enough.

R.M.W. classic rugby

R.M.Willians classic rugby shirt in green featuring embroidered logo and padded shoulders
R.M.Williams classic rugby shirt (Image: Provided)

When it comes to autumnal dressing, is there anything better than a classic rugby shirt? Well, R.M.W has officially perfected it this season. Crafted from comforting heavyweight cotton, it’ll keep you cosy through the season, while the padded shoulders add just the right touch of rugged appeal.

Heydude Wally NXT mid

product shot of Heydude Wally NXT moccasin-inspired shoes in brown suede
Heydude Wally NXT mid (Image: Provided)

Stepping into a new season means it’s time to step up your shoe game. Leave the flip-flops at the beach and save the trainers for the gym – because it’s moccasin season. The Wally NXT Mid was built for the autumn months before the frost calls for snow boots. Hairy suede meets buttery leather, HEYDUDE™ elastic laces make slipping in effortless, and the lightweight, flexible design keeps you moving all day. Slip in, step out, and let comfort do the talking.

VICKISARGE Bee cufflinks in platinum

VICKISARGE bee cufflinks in platinum with a bright green stone
VICKISARGE Bee cufflinks in platinum (Image: Provided)

Just because the season is changing doesn’t mean you have to let go of summer entirely. VICKISARGE signature Bee cufflinks add a pop of colour and a hint of sunny days to any shirt. Handcrafted in VICKISARGE’s Kensington workshop, each piece features cushion-cut crystals set in luxurious platinum plating. Consider them the perfect way to add a touch of individuality to your formalwear.

AMI double-breasted jacket

AMI brown double-breasted jacket
AMI double-breasted jacket (Image: Provided)

If anyone has perfected autumnal dressing, it’s the Parisians. So it’s no surprise that AMI’s autumn/winter 2025 collection has everything you need for a seamless transition wardrobe. This double-breasted coat is designed with straight fit tailoring, a notch collar, and horn buttons. Looking your best has never been so effortless.

Soft Goat polo shirt

Soft Goat polo shirt (Image: Provided)

A September style guide wouldn’t be complete without the perfect layering piece, à la Soft Goat. Where Scandi functionality meets the softest cashmere, their classic polo shirt was built for the transitional season. It layers as easily as it stands alone, moving seamlessly from crisp mornings to balmy afternoons. Clean lines meet subtle textures, making it as versatile as it is refined.