Have a date and don’t know what to wear? Anxiously rummaging through your closet—and your roommate’s—ten minutes before he picks you up? Here are a few dos and don’ts for looking the part on occasions when it matters most:

When you know you’ll see him out: While this isn’t a date per se, if you’re going out for a girls night but know he’s likely to be at the premeditated venue, here’s what you do: Aim to gain his attention without exposing too much (a rule that should be followed in all situations). Weather permitting, slap on a pair of high heels and a bandage skirt to play up your figure. Wear a sexy top and have fun with glitzy accessories. Do what it takes to get yourself noticed while still keeping it classy and maintaining the essence of your personal style.

First lunch/drink/coffee date: A daytime date generally evokes a more relaxed ambience, so go for the 3 C’s: comfortable, casual and chic. Given that this is a first date, you’ll be nervous enough, so the last thing you want is the itch of bad polyester. Try a skirt with tights and a stylish, yet classic pair of riding boots, or try a sundress if the weather is warm. Classy tip: Offer to split the check. If he’s interested in anything more than a friendship, he might not let you, but you don’t want to seem presumptuous on the first date.

First dinner date: Again, a first date is nerve-racking, so wear something comfortable. While evening attire gives you more leeway to turn up the sexy dial, you ultimately want him to remember you by your striking eyes or your addictive charisma, not your head-to-toe feather frock (regardless of the current trends) or your over-exposed chest (if this is the case, don’t expect him to listen to what you have to say). Keep it simple and pretty—nothing too distracting! Try a little black jersey dress, or for a more casual restaurant, black jeans and a top with a sweetheart neckline. (Avoid wearing regular jeans; this is a date, after all.) Obvious requirement: heels.

Hanging with his friends at his place: To fully gain the approval of your crush, you need to gain the approval of his friends. So here’s your plan of attack: hair down—most guys like it better. Regardless of the fact that you’re staying in and watching Monday Night Football, drinking beers and eating chips with dip—don’t wear sweatpants. Jeans and a girly top can be equally comfortable and are usually the more flattering option. Lastly, you don’t want to appear superficial, so don’t overwhelm them with a cornucopia of distracting accessories.

Fraternity formal: Here’s where you get to resurrect that beloved cocktail dress! This is not an outlet to emanate the season’s most eclectic trends. For example, shoulder pads, in the eyes of a college guy, are to be worn by linebackers and linebackers only. So to avoid this conversation, be sure to keep it classy, minimal and boy-friendly. That said, avoid the waistless shirt dresses, and gear yourself more toward a sheath dress with an accentuated waist line. If you’re feeling confident, a body-con dress is always a crowd favorite. Finish off your look with big statement accessories like a fun cuff or glitzy teardrop earrings.

Meeting the parents: You’ve all heard it before—dress conservatively for this one. A pair of black skinny jeans and a belted cardigan would be an acceptable look. For those who are a bit edgier, tone it down a bit. Avoid wearing black or grey, and try a more subdued color palette. Wear a feminine top—moms love ruffles! You want to look clean, sharp and put-together. Most importantly, wear a smile, sit up straight, and be polite.