Simon Baker’s Black Blazer & Checked Shirt Outfit
Simon Baker’s black blazer and burgundy checked shirt pair tailored lines with everyday denim. Brown chukka boots warm up the dark jacket, while black rectangular glasses repeat its color near the face. The open collar and blue jeans keep this a casual dinner outfit rather than a suit-and-shirt combination.
Outfit Details
Black Casual Blazer
Color: Black
Style: Casual
Fit: Regular
A black two-button blazer gives the checked shirt a plain frame. This regular-fit version has notched lapels and a lined body, so check the shoulders and waist with the shirt underneath. Fasten the upper button when standing if you want a more defined shape, leaving the lower button open. The sleeves should finish neatly at the wrist rather than cover your hands.
Burgundy Checked Shirt
Color: Burgundy
Style: Casual
Fit: Slim
A burgundy gingham shirt brings a small, regular pattern inside the black blazer. The selected cotton-polyester shirt has a slim cut, so compare its chest and waist measurements with a shirt you already wear comfortably. Keep the collar open and tuck the hem into the jeans to avoid a long patterned edge below the blazer. Let the burgundy supply the color without adding a tie.
Blue Straight Jeans
Color: Blue
Style: Casual
Fit: Straight
Blue Levi’s 514 straight jeans make the blazer feel less formal. Their regular thigh and straight leg offer a different shape from tightly tapered denim, with room to fall over the boots. Keep the wash simple so the checked shirt remains the main pattern. A short break works well here; a thick cuff would add another strong horizontal line beneath the tailored jacket.
Brown Leather Chukka Boots
Color: Brown
Style: Casual
Brown leather chukkas link the shirt’s warm burgundy tone with the blue jeans. This pair’s light sole gives the footwear a pronounced casual edge, so let the hem show the full toe and a little of the lacing. Their ankle height works with a straight leg that falls over the opening. Check the fit with your usual socks before deciding how much trouser length to keep.
Black Rectangle Glasses
Color: Black
Style: Casual
Black rectangular clear-lens frames repeat the blazer’s dark outline at the face. The listed frame width is 140 mm, so compare it with glasses you already find a good fit. These are a styling accessory; keep your own prescription frames if you wear them, since the outfit does not depend on this particular pair.
Why This Look Works
The blazer contains the small checks within a dark outline, making a patterned shirt easy to pair with jeans. Burgundy adds warmth without a bright block of color, and brown boots support that warmth lower down. Blue denim separates the black jacket from the footwear.
The straight jeans and light-soled chukkas relax the tailored upper half. An open collar keeps that balance consistent at the neck. Black glasses can echo the blazer, but the shirt, jacket and denim establish the combination even without them.
How to Wear This Look
Tuck the checked shirt
A smooth tuck leaves the blazer’s hem as the main edge at the waist. Check for excess shirt fabric at the sides before fastening the upper jacket button.
Keep the collar relaxed
Leave the top shirt button open and place the collar inside the lapels. A tie would change the relaxed balance created by denim and chukkas.
Avoid a heavy jean cuff
Use a short break over the boots instead. The light soles already create a visible edge, so there is little need for a thick roll of denim above them.
Ways to wear it
Color Alternatives
A blue-and-white checked shirt gives a cooler version. Keep the brown boots so the outfit still has a warm accent.
Accessories
Use the black glasses you already own or leave the frames out entirely. A plain belt, mostly hidden under the blazer, is enough at the waist.
Seasonal Adaptations
Add a longer dark coat for colder weather. Check that it fits over the blazer’s shoulders and sleeves so the tailored layer does not bunch underneath.
What to buy first
Put your attention into a black blazer that fits at the shoulders and a checked shirt that tucks cleanly. Then try the straight jeans with brown ankle boots to settle the hem length.
The burgundy shirt is the main color choice, while the glasses are optional. A good jacket fit and restrained denim will do more for the outfit than extra accessories.