Where Are You Headed
Knowing what's on the menu for the date makes it easier to choose an outfit. When headed out for a nice dinner, women can chose a flowy skirt and an embellished blouse, or slacks with a feminine, well-fitted top. Men look good in chino pants or slacks paired with either a short-sleeved shirt or a loose-fitting Oxford. Throw on a tweed jacket or blazer for an added touch. If you're movie bound, both genders can't lose in dark jeans, a thinly woven sweater and a casual pair of wing tips, sandals or thinly soled canvas shoes. If you're taking a stroll on the boardwalk after lunch, choose an outfit that is comfortable yet stylish. Cargo shorts, carpri pants, a polo shirt, layered tees and embellished outerwear are casual picks that go from day to night with ease.
What to Avoid
No one makes a good first impression when styled head to toe in trends. Choose one clothing or shoe trend and one color or fabric trend to build your outfit around. Also make sure to stay far away from loud or holiday inspired sweaters or sweatshirts blazoned with graphics, logos or sayings. Both men and women should avoid clothing that is too tight or too loose -- these are fashion faux pas and can send the wrong message about your personality. Make sure pants are tailored, jeans are a dark or vintage wash, and hems are the appropriate length.
Dress to Your Date
Try dressing to your date's style while staying true to your authentic fashion sense. If your female date tends to dress with more of an edge, stay away from your classic chinos and boat shoes. Instead, feel free to rock a dark-colored shirt, a pair of raw-denim jeans, and thick-soled shoes or a boot. If your date works near the shore and spends his free time surfing, you can be sure his style is casual. Choose cargo shorts and a well-fitted shirt and slip into a nice pair of strappy sandals or a canvas tennis shoe. Remember to use accessories such as eye wear, bracelets, a cool clutch, or a hat to add a distinctive style to your outfit.
Look to the Sky
Match your outfit to the season and you'll look good and feel comfortable for the whole date. When the weather turns cool, women can wear a well-fitted pair of dark jeans or thick leggings, a cable-knit sweater and cute flat shoes or mules to an afternoon date. Men look pulled together in jeans, a thin, chunky, V-neck sweater, a fine-knit turtleneck or a cool Henley left open to reveal a colorful tee underneath. At night, women can switch gears to an interesting heel and some sparkly jewels, while putting on a cropped jacket that flatters the waistline. Men can add outerwear such as a leather or military-style jacket and a masculine scarf that contrast with the shirt underneath.