Certain style moments are especially fraught. Growing up, it might be choosing a first day of school outfit, or that perfect summer camp get-up. As we get older, it’s choices like what prom dress to wear or what outfit is best for meeting your boyfriend’s parents. Before there are any parents to meet, though, you need to make it through at least a few successful dates, and that means you need some top-notch date night outfits. 

These 5 looks are sure to win his heart, no matter the season.

Casual Looks

There are many types of dates – a casual movie night or round of bowling, a trip to the beach, a fancy restaurant – and each demands a different sort of outfit. Most early dates, though, demand more casual looks, so let’s start there. Channel a cool, downtown vibe by combining a leather boot with denim. Depending on the weather, this outfit is flexible; jeans and a high boot will get you through the winter, while a shorter boot with a dress and denim jacket is perfect for spring.

Easy Accessories

Compared to choosing an outfit, the same accessories will carry you through different types of dates and different seasons. A simple leather handbag never goes out of style and with proper care, you’ll have it for years to come. Whether you prefer a clutch or a crossbody bag, leather can easily be dressed up for more formal occasions, go from day to night if you’re coming from the office, and so much more.

Give Him The Slip

Moving up a few degrees of formality, if you’re headed somewhere classy, but not too stuffy, why not try a slip dress? The slip dress is a date night staple, whether worn alone during the summer or with a wrap in colder weather. Slip dresses aren’t for the more modest among us – they’re little more than lingerie, but if you want to channel sultry vibes for Valentine’s Day or an anniversary date, a slip dress and heels covers all your bases.

A Romantic Romp

Are you planning a playful day at the beach or a night on the boardwalk? If so, a romper might be the perfect date night look. Having shed their childish associations, get flirty by choosing a romper with lace trim or a cutout. For cooler nights, you might choose a loose-fitting romper with pants, but don’t be afraid to show a little leg in a shorter one-piece.

Try Something Tailored

When headed to a fancy restaurant or a night at the theater, the simplest route from romantic to regal is to choose a carefully tailored piece. This might be your best fitted dress or elegant dress pants with a detailed statement jacket, any of which you can pair with delicate jewelry for a classy look that would fit in on the red carpet. 

With these date night looks on hand, you’ll be ready for any event, from that last-minute dinner with a Tinder match to a romantic anniversary dinner with your fiancé. Just don’t forget – the most attractive outfit of all is self-confidence. Hold your head high and know he’s lucky to have you on his arm.