For warm weather, wear something in a lightweight, natural fabric like wool, cotton, pima cotton, or silk. For instance, you might wear a cotton sundress with cute sandals or a pair of shorts and a flowy top. For colder weather, you could choose a nice pair of jeans or dress pants. Adding a printed blouse and a nice jacket, such as a pea coat, would take your look from everyday to dressed up.

For an active date, consider nice shorts, capris, or pants; a skirt or dress may make it more difficult for you to move around in. Pair your bottoms with a fun top; an off-the-shoulder blouse or a patterned tank top would work well. For a date at the movies, a restaurant, etc. you could choose a skirt or dress. Consider pairing your skirt with a sparkly tee or ruffled blouse. Adding a fun jacket or shrug over your dress is also a nice idea. A romper would also work well for this type of date.

You could lay out several types of outfits: a maxi dress with a bold belt and sandals; fitted jeans with a ruched top and boots; capris and a wrap top with heels; a skirt paired with a graphic tee and flats; or a sundress with a jacket and wedges.

If the weather is hot, avoid wearing tight clothes that will constrict you. Instead, wear something flowy and relaxed that will let you breathe and move.

A neutral top could be paired with colorful or printed bottoms, or neutral bottoms with a bold or patterned top.

If you normally wear jeans and tees, don’t opt for an evening gown unless the occasion calls for it (such as a black-tie affair). If your style is usually bohemian, for example, your date may be disappointed to see you in a preppy outfit.

There are tons of options out there: wedges, stilettos, booties, kitten heels, pumps, slingbacks, platforms, peep-toes, and mules, or ballet flats, sneakers, flat boots, moccasins, oxfords, etc.

Fashion designer Coco Chanel advises women to look in the mirror before leaving the house and to remove one accessory.

Women tend to dress better than men for dates. Everyone should dress for it, but not overdress for the occasion. [11] X Research source [12] X Expert Source Lisa ShieldDating Coach Expert Interview. 13 December 2018. A guy can wear a cool pair of jeans and a shirt that has been washed and not just pulled out of the laundry pile. You do not need to wear a tie. [13] X Research source [14] X Expert Source Lisa ShieldDating Coach Expert Interview. 13 December 2018. A woman should not show off too much skin. You can wear a revealing top and jeans or slacks, or a short skirt and a top that covers you properly. [15] X Research source [16] X Expert Source Lisa ShieldDating Coach Expert Interview. 13 December 2018.