Date Night Outfits: 18 Ideas for Dinner, Drinks and Weekends

The best date night outfit is one you forget you're wearing. You feel like yourself, a bit more polished than usual, and nothing pinches. Here are 18 ideas sorted by type of date, plus how to pick.

How dressy should you go?

Match the place, then go one small step up. A neighborhood bar: jeans with a great top. A nice restaurant: a dress or tailored trousers. Not sure? Smart casual is the safe middle ground.

Dinner at a restaurant

1. Slip skirt + fitted knit + ankle boots
2. Black wide-leg trousers + satin-look top + pointed heels
3. Wrap dress + delicate gold jewelry + block heels
4. Tailored blazer worn closed as a top + straight trousers
5. Midi knit dress + long coat + knee boots
6. Cream trousers + black bodysuit + statement earrings

Drinks and cocktail bars

1. Leather-look skirt + oversized shirt half-tucked
2. Dark straight jeans + one-shoulder top + strappy heels
3. Little black dress + denim jacket for a relaxed twist
4. Satin cami + cardigan + tailored trousers
5. Mini dress + sheer tights + loafers

Casual and daytime dates

1. White tee + wide-leg jeans + loafers + a good bag
2. Linen shirt dress + sneakers (summer)
3. Cream sweater + light jeans + white sneakers
4. Striped top + midi skirt + flats

Winter dates

1. Turtleneck + slip skirt + knee boots + long coat
2. Chunky knit + leather-look trousers + ankle boots
3. Knit co-ord (matching set) + wool coat

Tips that make any outfit better

• Comfortable shoes if there's any walking. Block heels or boots beat stilettos on cobblestones.
• One focal point. Earrings, a top or shoes: pick one statement.
• Plan layers. Restaurants are warm; the walk home isn't.
• Try it on earlier, not 20 minutes before you leave.

First date? See first date outfit ideas. Dressing a partner? There's a guide for date night outfits for men.

Try it with your own closet

Ask Wardrobely's AI stylist, "Dinner date at a wine bar, I want to wear my black trousers," and get an outfit from your own clothes. Then preview it with virtual try-on so you're not changing three times.

Frequently asked questions

What should I wear on a dinner date?

Something a step dressier than everyday: a slip skirt or tailored trousers with a nice top, a wrap dress or a knit dress, with comfortable heels or boots.

Can I wear jeans on a date?

Yes. Dark or well-fitting jeans with a polished top, good shoes and jewelry work for most casual dates.

What colors are best for date night?

Wear what you feel good in. Black, deep red, navy and cream are easy to style, but a color you love will always beat a "rule."