Dating at any age can be nerve-racking, intimidating, and stressful. None of these are looks you want to project! You want to look cool, confident, friendly, maybe even flirty. Let’s work with what you can control: your wardrobe. Your jitters will back off when your fashionable style comes forward.

Dressing for casual dates: coffee shop dates, a stroll in the park, Saturday lunch

You don’t want to be overdressed for casual dates but being underdressed might send the wrong message. You could come off looking aloof, bored, or like you don’t care. And you do! So let’s dress the part.

Outfit: Wear great-fitting jeans with a silk top or blouse paired with a cardigan or cropped leather jacket. Or wear a loose open weave sweater with a camisole underneath. Tuck the sweater into your jeans, just at the center front (a thumb tuck) and wear a great looking belt. A cute strappy sandal is perfect for warmer weather and boots or booties make a great choice for colder weather. Avoid running shoes.

Accessories: Wear your signature jewelry. Or if you’re wearing a thin sweater or long tunic, adorn your chest with thin, layered necklaces or a long pendant. A few bangles on the wrist are a nice touch.

Makeup: Go light on the makeup for your daytime look. No false eyelashes! Add color in your lipstick. Nails should be polished or at least manicured.

Dressing for evening dates: going for drinks, seeing live music, attending a comedy show

Evening dates mean you get to look more flirty, sexy, or sensual. No office attire! Here’s an opportunity to add sequins in moderation, ruffles, or bolder jewelry. Don’t shy away from expressing your personal style.

Outfit: Show off an asset of yours, just not all your assets at once. Consider a flirty low-cut top with full pants. Or try wearing a shorter print skirt with a modest top or easy-fitting sweater. Wear heels or booties if you aren’t going to be standing a lot. Dresses are a great option. Cotton or jersey knit dresses that follow your curves without clinging to them are easy and comfortable to wear. Stay away from formal wear.

Accessories: A small clutch with gemstones or a cross-body bag with a chain strap work well. Chandelier earrings or large hoops are fun. Consider scarves and pretty gloves for warmth.

Makeup: You can go heavier on the makeup with more blush, eyeshadow trios, and/or a bold lipstick color. Dare to add a few false eyelashes.

Dressing for formal dates: dinner out at a nice restaurant, art show openings, fundraisers, a guest at a wedding or a graduation

Have fun with this one. You can be creative, artistic and modern. Or be sophisticated and classy. Just don’t be too conservative; it could make you look stuffy. We know how fun you are. Your date should too.

Outfit: Wear something that you feel radiant in. Maybe it’s a delicious color that you wear beautifully. Maybe it’s an outfit that has sheer qualities to it either in cut outs, lace, or see-through fabrics. If necessary, wear the appropriate undergarments so you’re not coming off too racy. Or go for a classic tuxedo pant and ivory satin blouse or a high-waisted skirt paired with a simple knit top tucked in. Wear patent pumps (your choice of color), patterned flats, or dressy heeled sandals.

Accessories: Fill in a deeper neckline with multiple strands of pearls or wear a statement necklace. Draw attention to your face with dazzling earrings. Add a cocktail ring or two. Be sure to carry an evening bag, not a hobo bag.

Makeup: Give yourself time to prep and primp. Consider getting your hair and makeup done professionally earlier in the day. If you’re doing this yourself, dramatic makeup and styled hair can take time. Plan for it.

Dressing for active dates: hikes, sailing, playing golf

You’re not going to the gym or on a run. You’re going on a date. Make sure your outfit conveys that distinction.

Outfit: Sweaters, vests, and jackets are essential for layering for the outdoors. It’s hard to carry on a conversation if your teeth are chattering! Remember, you can look sporty without being in workout gear. Choose clothing pieces that are easy to move in. Consider having the layer closest to your skin be one made from tech fabrics that wick away moisture and odor.

Accessories: Scarves are necessities for protecting you if the wind picks up and they’ll add style to your outfit. Sunglasses are a must. Hats can be your partners in fashion: try fedoras, wide-brimmed hats, straw hats, or baseball styled caps that aren’t team-specific. Keep jewelry to a minimum so nothing gets in the way of your activities.

Makeup: Make sure your makeup won’t melt if you work up a sweat. Light foundation, sunscreen, mascara, eyebrow definition and a light lipstick will do.

Need Assistance?

If dressing for dates makes your head spin, let me help. I can get you dressed for any type of date so that you can feel confident and look great. We’ll do what we can and leave the rest to fate!