Anniversary Dinner and Date Night Outfits for Women in Their 30s and 40s

For an anniversary dinner or a date night, dress 1 step above the restaurant. Wear a midi dress, a lace jumpsuit or a satin blouse with black pants, and choose a coat for the walk to the restaurant. The Greta Off-Shoulder Dress in Navy ($695) is a midi with an off-shoulder band, silver buttons and a pleated skirt with pockets. Luna lists its length, 46 inches from the back of the neck on a size 2, and the length of the coat. That tells you before you order that 4 inches of skirt will show below the Paula coat.

What do I wear to a fine dining dinner?

Start with the restaurant. Many restaurants state a dress code on the reservation page. A tasting menu or a hotel dining room usually expects a midi dress, an evening jumpsuit or tailored pants with a satin top. At a neighborhood restaurant, a knee length dress or pants with a blouse is enough.

A private wine dinner in a cellar runs cool, so bring sleeves or a layer. For a milestone anniversary, wear what you would wear as a wedding guest. For a first date, pick something you already feel at ease in. A dress or pants work equally well at all of them.

Anniversary and date night outfits in your 30s and 40s

Date night in these years often starts straight from work. The workday ends at 6 and the table is booked for 7:30. There is no time to go home and change. The same month may also hold a wedding, an office party and a client dinner. Buy the dinner dress for all of them, and decide 2 things first: the length you want at the table and whether the outfit has to start the day at work.

The midi for a milestone

The Greta has a structured bodice that holds the off-shoulder band in place through a seated dinner and a dance afterward. Its page names black tie optional weddings and charity galas among its evenings, so the anniversary dress also covers the next formal invitation. It is machine washable on a gentle cycle.

The Melissa Strapless Dress in Black Polka Dot ($770) is a satin corset midi with an A-line skirt. Its removable strap goes around the neck as a halter or comes off for a strapless line, so you can wear it 2 ways. The corset holds its line through a long seated dinner. Like the Greta, it measures 46 inches on a size 2.

Straight from the office

The Olga Wrap Dress in Navy ($695) is a knee length wrap with short sleeves, a notched lapel collar, gold-tone buttons down the wrap and a buckled belt. It measures 39 inches on a size 2. Its page pairs it with a black blazer for an executive luncheon. Wear it that way to work, then take the blazer off for dinner. Worn to 4 events in a year, the $695 comes to under $175 a wearing.

If you would rather wear pants, the Talia Satin Blouse in Black Polka Dot ($425) is sleeveless, with a V neckline and a diagonal button line. Tuck it into black wide leg pants and keep a blazer over it until you leave the office. It is machine washable.

Lace, satin or metallic

The Jody Lace Jumpsuit in Bordeaux ($550) is sleeveless, with a lace bodice in deep wine over a fitted underlining, a sheer illusion yoke and a slim belt with a buckle. Solid wide legs fall from the belt. With wide legs in place of a long skirt, you can walk after dinner without holding up a hem. Its page asks you to check the inseam against the heel you plan to wear.

For a rooftop or a cocktail bar where you stand more than you sit, the Laura Short Metallic Dress in Bronze ($595) is fitted, with a crinkled metallic surface. A draped neckline sits across the collarbone, and ruching runs across the bodice, the waist and the hip. It finishes above the knee and measures 34 inches on a size 2.

Our guide to wedding guest dresses for women in their 30s and 40s shows how 1 dark dress changes with the coat and the shoes. If you are choosing your first evening dress, read our guide to choosing a cocktail dress in your 30s.

What to wear over it by season

Between October and March, choose the coat by the hem. The Paula Textured Coat with Faux Fur Collar and Cuffs in Black ($770) is a textured black coat with a faux fur shawl collar and faux fur cuffs, lined in Bemberg. It measures 42 inches on a size 2. It covers the Olga by 3 inches and the Laura by 8 inches. Over the Greta and the Melissa, 4 inches of skirt show below the coat. Over the Jody jumpsuit, the wide legs fall below the coat to the shoe. The Paula is dry clean only.

In summer, a restaurant is often air conditioned and a terrace cools fast after sunset. Carry a blazer or a wrap for the table. The guide to winter date night outfits pairs more coats with dresses.

What to avoid

Skip a neckline or a strap that needs adjusting through dinner. Skip shoes you have not worn for an hour at home. At a wine dinner, a deep color is safer than a pale one. On a windy terrace, a short metallic dress needs a coat that closes.

Shoes and bag

Wear a heel you can walk 2 blocks in for the trip from the car. A slingback or a pump with an ankle strap stays on through a long evening. Carry a small clutch or a shoulder bag that fits on the table or the seat beside you.

For Valentine’s Day or Mother’s Day, read our guide to Valentine’s dinner and Mother’s Day brunch outfits. For a party with guests, read what to wear to a milestone anniversary party. Every piece above is in anniversary and date night outfits, and every other event is on the Shop by Occasion page.

A short checklist

• Check the restaurant’s reservation page for a dress code.
• Dress 1 step above the restaurant.
• Decide whether the outfit has to start the day at work.
• Choose the coat by the length of the hem.
• Wear the shoes at home for an hour before the evening.

Questions about anniversary dinners and date nights

What should I wear to a milestone anniversary dinner?

Wear the dress you would choose as a wedding guest: a midi or an evening jumpsuit in navy, deep wine or black. The Greta Off-Shoulder Dress in Navy and the Jody Lace Jumpsuit in Bordeaux both suit a hotel dining room or a tasting menu. Add a coat that suits the length.

Should I wear a dress or pants on a date night?

Either works. A dress suits a restaurant with tablecloths. An evening jumpsuit, or a satin blouse with black wide leg pants, suits a wine bar or a dinner followed by a walk.

What is a good romantic dinner outfit that is not too revealing?

Choose lace, satin or a deep color in place of bare skin. The Jody Lace Jumpsuit in Bordeaux has a sheer illusion yoke over a lined lace bodice. The Melissa Strapless Dress in Black Polka Dot can be worn with its strap at the neck as a halter.

What do I wear to a private wine dinner?

Wear a dark or deep color that hides a drop of red, with sleeves or a layer for a cool cellar, and a hem that works seated. The Olga Wrap Dress in Navy has short sleeves and a knee length hem.

How do I go from the office to a date night?

Wear a dress that works at your desk and add 1 change at 6. The Olga Wrap Dress in Navy goes to work under a black blazer. Take the blazer off for dinner, and the gold-tone buttons and belt dress it up.

Does Luna ship free, and can I return a piece?

Shipping to any US address is free. Orders ship from California and arrive in 2 to 5 days, and you can return any order within 30 days with no questions asked.