Before the pandemic started, my husband and I usually went out with other couples on Saturday nights. We would watch a movie, order take out or have another couple over for socially distanced drinks outside. But then, to stay safe and healthy, we started saying in more often.

Now we are ready to get back to going out on the weekends, but my closet is not! After months of changing from my daytime sweatpants to clean, evening ones, it is time to get dressed up again, and I have no idea what to wear.

Cute Date Night Outfits 

If you are having some of the same feelings, don’t worry! We are ready with some fashion tips for date night from the experts.

Make Sure It Fits

If your clothes don’t fit, don’t flatter, or you don’t feel good in it, donate, toss or consider selling the item at a consignment shop. Priya Virmani, stylist and owner of the styling service,  Privee by Priya, advises, “Take a very close look at the condition of your clothes. Stains, tiny rips, piling need to be addressed. Also, any denim over five years old is likely not the best fit or style.”

The Whole Outfit Matters

For a restaurant date, don’t be fooled into thinking only the top counts (this isn’t a Zoom call – people can see what you are wearing on the bottom). Virmani says, “While you don’t need to worry too much about your shoes, you do want an overall look that should be satisfying and empowering. Beyond clothes, also pay attention to your jewelry and make-up.”

Evening Sweaters

For winter nights out, sweaters can be very cozy. Ashley Sanchez, a stylist at Stitch Fix, advises, “If you’re gravitating towards rocking a sweater for an upcoming date night, focus on finding options that feel a bit special. Avoid crew necks that can give off a business vibe and not seem special. Instead, look for sweaters with interesting silhouettes, such as cut-out details, embellishments, illusion, lace, off-the-shoulder cuts, or sweetheart necklines.”

White House Black Market Chenille Sweater
White House Black Market Off-The-Shoulder Chenille Sweater, $19.99+
French Connection Caballo Sweater
French Connection Caballo Sweater, $118
Karen Millen Cashmere V Neck Jumper
Karen Millen Cashmere V Neck Jumper, $136

More Than Basic Black

Think a black blouse is too boring? It doesn’t have to be. Sanchez says, “Reach for options with romantic details like lace, sheen, and shine or unique silhouettes, including asymmetrical hems or cut-outs. Black is also a great option to pair with printed bottoms.” A black top is also the perfect plain canvas. “Layered gold necklaces, a statement piece, or bold scarf can all easily breathe new life into your favorite black blouse.” Or for a change, choose a white blouse. “Accessorize a white blouse with a fur (faux works) vest, a blazer, or a moto jacket,” suggests Virmani.

Miholl Long Sleeve Lace Blouse
Miholl Long Sleeve Lace Blouse, $22.99
Bellivera Faux Leather Short Moto Jacket
Bellivera Faux Leather Short Moto Jacket, $54.99+
1.State Plaid One Button Blazer
1.State Plaid One-Button Blazer, $139

Cocktails Mean You Will Be On Your Feet

Sanchez says, “Ensure your footwear won’t be the nuisance of the night. While you may feel compelled to bust out your newest heels, keep in mind just how long you’ll be on your feet.” Choose pretty but practical shoes; a flat, kitten heel or wedges are all great alternatives. Comfortable statement shoes are great but save your pointy, high heels for nights when you will mostly be sitting at the table, and your only walks are to the bathroom. Also, consider wearing a color. Virmani says, “Cocktail parties tend to be a sea of people dressed in black. A color will make you stand out from the crowd and be more memorable.” And it will be easier for your date to find you if you need rescuing from a boring conversation!

Bella Vita Quilla Kitten Heel Pump
Bella Vita Quilla Kitten Heel Pump, $27.13+
Anne Klein Timeout Wedge Heels
Anne Klein Timeout Wedge Heels, $66.31+
Jewel Badgley Mischka Bambi Slingback Flats
Jewel Badgley Mischka Bambi Slingback Flats, $89

Invest in a Fun, Warm Outerwear

You may find yourself eating outside, and even though heat lamps provide warmth, you still may not want to take off your jacket. Now is the perfect time to buy a coat that combines function and fashion. Sanchez says, “I recommend an on-trend puffer jacket. The puffer has quickly become the must-have outerwear piece of the season. From cropped to ankle-length silhouettes, bold patterns to neutral shades, there’s a puffer jacket out there for everyone.” If you prefer a dressier look, try a wool coat or faux fur/shearling jacket.

Karen Millen Mid Length Puffer Coat
Karen Millen Down Filled Packable Mid Length Coat, $133.20
Women's Liv Outdoor Sami Short Puffer Jacket
Women’s Liv Outdoor Sami Short Puffer Jacket, $59.99
Karen Millen Wide Collar Faux Fur Coat
Karen Millen Wide Collar Faux Fur Coat, $308.80

Be Comfortable

While you probably don’t want to wear your sweatpants out to dinner, that doesn’t mean you have to suffer and be uncomfortable. “Instead of tight jeans, consider wearing trousers which are roomier,” says Virmani, “Or leather pants with an elastic waistband.” Dresses are another comfortable evening option. Sanchez says, “Dresses or skirts are good options as they offer breathability depending on the silhouette. A-line options are particularly forgiving and flattering. If you are sitting down most of the date, choose fabrications that don’t wrinkle too much, such as polyester blends.” If you are worried about being chilly, wear opaque tights or high boots.

Nordstrom Faux Leather Leggings
Nordstrom Faux Leather Leggings, $59
Alfani Wide Leg Pull On Pants
Alfani Wide Leg Trousers, $59.50
Calvin Klein Puff Sleeve A Line Dress
Calvin Klein Puff-Sleeve A-Line Dress, $89.98

Most important, wear date night clothes that make you feel good. Sanchez says, “Head into your closet with confidence, so you can walk out the door not only looking but feeling your best.”


Disclosure: This post contains affiliate links.

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