Date Night Ready | Connor

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.