Date-Night Dressing​

Date-night ready. No stress.​

Valentine’s Day plans? Last-minute dinner? A Friday night that accidentally turns into a proper one?​

This is your sign to level up the fit - without blowing the budget.​

Connor date-night looks are sharp, comfortable, and built for going out. These are outfits that feel as good as they look, so you can focus on the night, not the mirror.​

The Formula: Go-Out Outfits That Actually Work​

The best date-night fits are simple. Nail these three things and you’re sorted:​

Great pants (chinos, jeans, cargos)​

A clean top (smart polo or shirt)​

A light jacket for the walk in — and the icy air-con inside​

From there, it’s just choosing your lane.​

​

LOOK 1: Smart Polo + Tapered Chino​

The easy win - sharp with zero effort.​

Hero styles:​
DARIO Smart Polo or GENOA Smart Polo​
HENDON Tapered Chino​

Why it works: Hendon chinos are built for day-to-night wear, with stretch fabric, an elasticated back waistband for a better fit, and a finish that looks sharp while resisting creases all day.​

Finish it with:​
Clean sneakers or smart lace-ups​
Simple belt​
No-show socks (or crisp crew socks if you want it more street)​ ​

LOOK 2: Relaxed Fit Shirt + Overshirt​

Cool, layered, and ready for whatever happens after dinner.​

Hero styles:​
BARLOW SP Shirt or BONDI SP Shirt (new relaxed fit)​
CLARKE Overshirt (C26CS107) in Black or Stone​
Pair with chinos or relaxed jeans.​

Why it works: The relaxed fit keeps it modern, the overshirt adds structure, and the whole look feels put together without ever feeling stiff.​

Finish it with:​
Leather-look sneakers or loafers​
Sunnies (for the pre-dinner walk)​
Belt​ ​

LOOK 3: Short Sleeve Shirt + Loose Jeans​

Hot night out? This one’s built for it.​

Hero styles:​
TOTTI Shirt​
PUNT Shirt​
BOWERY Shirt​
BLEEKER Shirt​
ACLAND Boxy Shirt​
PRINCE Boxy Shirt​

Wear it with:​
NEW EDDIE Loose Jean (3 washes)​

Why it works: Short sleeve shirts keep things breathable, while loose denim delivers comfort with a modern silhouette.​

Finish it with:​
Clean white or black sneakers​
Crew socks (or no-shows, depending on the shoe)​
Tonal belt​ ​

LOOK 4: Relaxed Fit Jeans + Smart Top​

The easiest pants to style — tees to shirts, you’re sorted.​

Choose your denim:​
DALSTON Relaxed Jean​
MURPHY Relaxed Jean (2 washes)​
WILEY Relaxed Jean​

Top it with:​
A smart polo (Dario or Genoa) for a cleaner vibe​
A relaxed fit shirt (Barlow or Bondi) for something more “going-out”​

Finish it with:​
Minimal sneakers or dressier shoes​
Belt​
Clean socks (no wild patterns unless you mean it)​
Light jacket if you’re heading out late​ ​

LOOK 5: Cargo or Statement Pants + Simple Top​

When you want the fit to do the talking.​

Try these pants:​
CAVALIER Check​
BRANDON​
HENDON (multiple colours)​
DIXON Loose Chino​
Keep the top clean — a smart polo or plain shirt — and let the pants be the hero.​

Finish it with:​
Black belt (always safe)​
Sleek sneakers or lace-ups​
Neutral socks​
Sunnies for day-to-night​ ​

LOOK 6: Add a Light Jacket = Instant Upgrade​

Because it’s not just the fit — it’s the finish.​

Throw one over a polo or shirt:​
DANNY Bomber Jacket — Black​
ZANE Jacket — Navy or Stone​
OUTLANDER Jacket — Black or Stone​
This is the fastest way to make any outfit feel instantly more “date-night”.​

Finish it with:​
Dress sneakers, loafers, or derbies​
Matching belt and shoe tones (if you want to look extra switched on)​
A neat watch and clean wallet​

​The Date-Night Accessories Checklist​
Keeping it simple? These do the most work:​

Shoes: Clean sneakers, loafers, or smart lace-ups​
Belt: Keep it tonal (black/black or tan/tan)​
Sunnies: Understated frames​
Socks: No-show for sleek, crew for street​
Watch + fragrance: Small details, big upgrade​ ​
Final Word Date-night ready.​ Great fit.​ Good quality.​ Better value.​

Now all you need is the plan.​