Whether it’s your first date, subsequent dates, or that one night a month you and your partner finally get to be alone, your date-night style strategy should remain the same: to look stylish, put together and yes, sexy, but tasteful. Below are my three rules to look your best on a date.
The first rule is to dress appropriately for the venue (and consider the weather). Dinner and a movie? Your attire should involve denim/casual pant, a button-up shirt or sweater layered with a jacket and finish off with your favorite boots. Dinner at a city’s hotspot? A dress worthy of the three-month wait for a reservation. An Athletic Date? Consider comfort, of course, but it is still a date, so put on your best athleisure, and yes, look polished. You get the idea.
The second rule is to love how you look. The whole point of a date is to have fun, flirt and reveal your best side – to get to know each other. If you are already a couple, then time to reconnect with no distractions. You won’t be able to do that if you dislike what you’re wearing or if your choice makes you fidget. If it reminds you of another bad date or a non-positive event, or if you think it’s time to put it in the donation pile – do not wear it! Wear something that gives you joy when you look in the mirror – or perhaps you now have an excuse to go shopping.
The third rule is don’t stress. If you do, you won’t just be wearing an outfit, you’ll be wearing your anxiety on your face and in your body language. Before you leave that front/side or back door remind yourself that you look good. Confidence is everything.
Here are a few of my favorite date night looks.
- A version of the LBD (try color or print – be bold), booties or heels
- Jeans, button-up top or t-shirt with a tweed blazer and dressy loafers
- A fitted top, wide-leg trousers and heels
- Pin-striped pants, a flowy tank and moto jacket with kitten heels
- Printed silk blouse, high-waisted dark jeans and ankle boots/heels
- Menswear-inspired white shirt, distressed jeans, and heels
- A white flowy blouse, tailored black pants and peep-toe shoes
- A bold color sweater, perhaps with some cut-outs or a low back, black or navy cigarette pant and pointed flats/heels
- A knit dress with a thigh length jacket and over-the-knee boots
- Printed jacket over a monochrome outfit
- Chunky knit sweater, fitted skirt and heels
- Camel color coat, cashmere/light wool fitted sweater and dark denim/pants with ankle string wrap-around mules
- Shirt dress, crossbody bag and a sandal
- Sweater dress and moto boots (not too chunky)
- Statement blouse (lace, beaded or sequined), jeans/pencil skirt/A-line skirt and sling-backs
- A maxi or mid length strappy silk dress with a stiletto heel sandal – add a crop jacket (leather, faux leather or faux fur) for a little bit of edge
- A tailored pantsuit or slightly over-sized (keep it feminine) with layered necklaces as your underpinning