Autumn Smart Casual Outfit Guide

The Looks

scored by harmony

British Prep

Waxed Jacket · Tattersall Check Shirt · Corduroy Trousers · Chelsea Boots

score

Outerwear

Waxed Jacket

€€€

Expensive

Timeless

Try-hard

Shirts

Tattersall Check Shirt

€€

Expensive

Timeless

Try-hard

Trousers

Corduroy Trousers

€€

Expensive

Timeless

Try-hard

Shoes

Chelsea Boots

€€€

Expensive

Timeless

Try-hard

+ Add Classic Dress Watch €€€€

British Prep

Tweed Sport Coat · Oxford Cloth Button-Down · Khaki Chinos · Chelsea Boots

score

Jackets & Blazers

Tweed Sport Coat

€€€

Expensive

Timeless

Try-hard

Shirts

Oxford Cloth Button-Down

€€

Expensive

Timeless

Try-hard

Trousers

Khaki Chinos

€€

Expensive

Timeless

Try-hard

Shoes

Chelsea Boots

€€€

Expensive

Timeless

Try-hard

+ Add Classic Dress Watch €€€€

Old Money

Trench Coat · Oxford Cloth Button-Down · Khaki Chinos · Chelsea Boots

score

Outerwear

Trench Coat

€€€

Expensive

Timeless

Try-hard

Shirts

Oxford Cloth Button-Down

€€

Expensive

Timeless

Try-hard

Trousers

Khaki Chinos

€€

Expensive

Timeless

Try-hard

Shoes

Chelsea Boots

€€€

Expensive

Timeless

Try-hard

+ Add Classic Dress Watch €€€€

Quilted Jacket · Oxford Cloth Button-Down · Khaki Chinos · Chelsea Boots

score

Outerwear

Quilted Jacket

€€

Expensive

Timeless

Try-hard

Shirts

Oxford Cloth Button-Down

€€

Expensive

Timeless

Try-hard

Trousers

Khaki Chinos

€€

Expensive

Timeless

Try-hard

Shoes

Chelsea Boots

€€€

Expensive

Timeless

Try-hard

+ Add Classic Dress Watch €€€€

Ivy League

Puffer Vest · Oxford Cloth Button-Down · Khaki Chinos · Chelsea Boots

score

Outerwear

Puffer Vest

€€

Expensive

Timeless

Try-hard

Shirts

Oxford Cloth Button-Down

€€

Expensive

Timeless

Try-hard

Trousers

Khaki Chinos

€€

Expensive

Timeless

Try-hard

Shoes

Chelsea Boots

€€€

Expensive

Timeless

Try-hard

+ Add Classic Dress Watch €€€€

British Prep

Tweed Sport Coat · Oxford Cloth Button-Down · Corduroy Trousers · Chelsea Boots

score

Jackets & Blazers

Tweed Sport Coat

€€€

Expensive

Timeless

Try-hard

Shirts

Oxford Cloth Button-Down

€€

Expensive

Timeless

Try-hard

Trousers

Corduroy Trousers

€€

Expensive

Timeless

Try-hard

Shoes

Chelsea Boots

€€€

Expensive

Timeless

Try-hard

+ Add Classic Dress Watch €€€€

Old Money

Trench Coat · Oxford Cloth Button-Down · Corduroy Trousers · Chelsea Boots

score

Outerwear

Trench Coat

€€€

Expensive

Timeless

Try-hard

Shirts

Oxford Cloth Button-Down

€€

Expensive

Timeless

Try-hard

Trousers

Corduroy Trousers

€€

Expensive

Timeless

Try-hard

Shoes

Chelsea Boots

€€€

Expensive

Timeless

Try-hard

+ Add Classic Dress Watch €€€€

British Prep

Waxed Jacket · Tattersall Check Shirt · Khaki Chinos · Chelsea Boots

score

Outerwear

Waxed Jacket

€€€

Expensive

Timeless

Try-hard

Shirts

Tattersall Check Shirt

€€

Expensive

Timeless

Try-hard

Trousers

Khaki Chinos

€€

Expensive

Timeless

Try-hard

Shoes

Chelsea Boots

€€€

Expensive

Timeless

Try-hard

+ Add Classic Dress Watch €€€€

British Prep

Waxed Jacket · Tattersall Check Shirt · Navy Chinos · Chelsea Boots

score

Outerwear

Waxed Jacket

€€€

Expensive

Timeless

Try-hard

Shirts

Tattersall Check Shirt

€€

Expensive

Timeless

Try-hard

Trousers

Navy Chinos

€€

Expensive

Timeless

Try-hard

Shoes

Chelsea Boots

€€€

Expensive

Timeless

Try-hard

+ Add Classic Dress Watch €€€€

British Prep

Waxed Jacket · Tattersall Check Shirt · Pleated Trousers · Chelsea Boots

score

Outerwear

Waxed Jacket

€€€

Expensive

Timeless

Try-hard

Shirts

Tattersall Check Shirt

€€

Expensive

Timeless

Try-hard

Trousers

Pleated Trousers

€€€

Expensive

Timeless

Try-hard

Shoes

Chelsea Boots

€€€

Expensive

Timeless

Try-hard

+ Add Classic Dress Watch €€€€

Quilted Jacket · Oxford Cloth Button-Down · Corduroy Trousers · Chelsea Boots

score

Outerwear

Quilted Jacket

€€

Expensive

Timeless

Try-hard

Shirts

Oxford Cloth Button-Down

€€

Expensive

Timeless

Try-hard

Trousers

Corduroy Trousers

€€

Expensive

Timeless

Try-hard

Shoes

Chelsea Boots

€€€

Expensive

Timeless

Try-hard

+ Add Classic Dress Watch €€€€

Ivy League

Puffer Vest · Oxford Cloth Button-Down · Corduroy Trousers · Chelsea Boots

score

Outerwear

Puffer Vest

€€

Expensive

Timeless

Try-hard

Shirts

Oxford Cloth Button-Down

€€

Expensive

Timeless

Try-hard

Trousers

Corduroy Trousers

€€

Expensive

Timeless

Try-hard

Shoes

Chelsea Boots

€€€

Expensive

Timeless

Try-hard

+ Add Classic Dress Watch €€€€

Key Pieces

Autumn · Smart Casual

Shirts

Oxford Cloth Button-Down

The foundational Ivy League shirt. OCBD collar rolls naturally. Never iron flat.

€€

Trousers

Khaki Chinos

The prep trouser. Slightly relaxed fit, natural waist. Never skinny.

€€

Trousers

Navy Chinos

Navy chinos replace jeans in most prep contexts. Cleaner, more intentional.

€€

Knitwear

V-Neck Sweater

Over the OCBD. The Ivy uniform. Merino wool. Navy, grey, or burgundy.

€€

Accessories

Classic Dress Watch

Simple dial, leather strap. No date window preferred. Timex to Patek — it's about restraint.

€€€€

Jackets & Blazers

Tweed Sport Coat

Harris Tweed or herringbone. The British countryside in jacket form.

€€€

Knitwear

Crew Neck Sweater

Versatile and clean. Works as a layering piece or standalone.

€€

Outerwear

Waxed Jacket

Barbour or similar. British countryside institution. Ages beautifully.

€€€

More Looks

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