How to Dress for a First Date

girl changing dresses

Arriving for a first date decked out in the wrong attire is awkward and uncomfortable. Here are some common dating scenarios matched with outfit suggestions to help you relax, enjoy and avoid the nightmare that is the sequined mini-dress at the pub.

The Coffee Date

You’re best off with casual day or night attire, as the time of the date dictates. For guys, this means a clean, wrinkle-free T-shirt and tidy jeans. For girls, a soft, subtly sexy sweater and jeans or pants is the ultimate in laidback coffee date chic. A ‘conversation piece’ also makes a nice addition – an heirloom watch, a quirky umbrella (if warranted) or a worn leather bag all complete an outfit and give the wearer a great conversation starter should the need arise.

Fashion hazards: Don’t wear anything made from delicate (read: dry-clean only) fabrics. There’s too many opportunities for you to get into a mess with coffee and cake residue, so stick to clothes you can toss in the machine on wash day.

Museum / Gallery Hopping

An easy-going option is jeans or pants and a quirky, well-fitting blouse teamed with an interesting necklace or brooch. Just remember that good walking shoes are a must, you can cover some serious ground traipsing through various exhibitions on multiple floors. Don’t forget a lightweight jacket as museums can be notoriously chilly.

Fashion hazards: Girls, leave the strappy heels at home. Not only are they hell on your feet but your fellow patrons won’t have to listen to the incessant clip-clop of your footwear on the shiny gallery floors.

Market Day / Antique Trawling / Second-hand Bookstore Browsing

Something old, something new is the order of the day when scouring the markets. An ethnic-inspired dress or skirt teamed with a fitted T-shirt and arty necklace is a great look.

Fashion hazards: There’s nothing more frustrating than trying on clothing at markets — except trying on clothing at markets when you have worn too many layers and fiddly lace-up shoes. If you’re in search of some bargain retro clothing, make sure your outfit is easy to get in and out of.

Dress for comfort: Now’s not the time for an extreme wardrobe makeover.

Bowling / Cycling / Outdoors Activities

Action-packed first dates require comfortable clothing that’s fashionable enough to make you look appealing to your date while offering the level of comfort and flexibility your activity requires. A favorite pair of jeans with a snug (but not too snug) fit and a little ‘stretch’ in them works well. Team these with a cool polo shirt and a pair of sneakers (street-style are fine unless you’re doing something really athletic that requires a cross-trainer).

Fashion hazards: All that activity can get you hot under the collar, so make sure you don natural, breathable fabric and plenty of deodorant. Keep in mind that many lighter shades can show up sweat marks, so stick to dark-colored tops.

Pub Bistro / Pub Trivia

Just because you’re at the pub doesn’t mean you have to dress scruffily.  Keep makeup natural and save the shiny, glitzy outfits for the dance floor. A sexy fitted top or shirt and pants are fine with a pair of ballet flats or kitten heels on your feet.

Fashion hazards: Unless you want the whole world to see your knickers when you’re seated on a bar stool, leave something to the imagination – and leave your miniskirt in the closet.

How to Pick a Fail-proof Outfit

Dress for the weather: If in doubt, take a jacket and an umbrella if the weather looks uncertain. It’s far better to be carrying a coat than to be shivering and wet.

Think about the venue: A classy restaurant deserves your best outfit – and so does your date. Be mindful of over-dressing or under-dressing for the occasion.

Dress for comfort: Now’s not the time for an extreme wardrobe makeover. Stick to garments you usually wear so you’ll feel comfortable and confident.

Choosing an outfit that’s suitable for your scheduled date activity or venue takes a little thought and planning. But knowing that you’ve dressed the part will give you a sense of confidence that will help make the first date a success.

About Lavalife

Lavalife is one of the founding dating sites known to online daters. With the most experience in the dating space, Lavalife publishes content by authors who have influenced thousands of daters looking for great advice.
Scroll To Top