Suited Guide

What to wear on a first date without looking like you tried too hard

The target is one notch dressier than the venue, in clothes that fit and feel like you. Confidence reads louder than any garment; discomfort reads loudest of all.

Dinner date

Dark straight-leg jeans or chinos, an unstructured blazer or fine knit over a fitted tee or open-collar shirt, leather boots or loafers. This is the highest-return formula in menswear.

Drinks

Slightly more relaxed: overshirt or bomber over a quality tee, dark denim, clean sneakers or suede boots. One interesting piece (texture, not slogan) gives her something to notice.

Coffee or daytime

Effortless is the brief: well-fitting jeans, an unfussy shirt or polo, casual footwear in good condition. Over-dressing a coffee date is its own kind of miss.

The three checks

• Fit: shoulders, sleeve length, trouser break. Tailored beats expensive.
• Condition: no pilling, no scuffed shoes, no stretched collars.
• Comfort: if you'll fidget in it, don't wear it.