The Best Places To Dress Up In An Increasingly Casual World

It can seem to some of us who love dressing up now and then that there are fewer and fewer places that welcome formal attire these days. The world is getting more casual, beginning with offices but spreading out more widely, and while this can be nice at time, it also means that the nicer dresses in your closet may be yearning to get out more. If this is something you’ve been feeling lately, or even for the last decade, trust us – we know what you’re dealing with. And it’s or that reason that we’ve done some thinking about some places and occasions where you can still regularly get away with more formal attire (aside from the obvious, like a fancy date night).


Most cruises have at least one formal dinner night per trip; longer cruises might have two or three. Granted, this can make packing a little difficult, because many people don’t have several evening gowns just laying around waiting to be worn out. But a little shopping is well worth the effort when you’re handed an opportunity to showcase your formal fashion sense. You can meet other travelers (and sometimes the captain and crew), and enjoy a little extra glitz and glam in the midst of a trip that’s likely to be fairly casual otherwise.

Of course, if you want to dress up a little more often on your cruise, you can always pack some sundresses for the excursions in your ports-of-call. Others may be in shorts and tank tops, but a sundress is the perfect mix between dressed up and casual, and can help you feel stylish as you explore a fun new place. Plus, you’ll likely have the perfect excuse to try out a fashionable new hat, a pair of sunglasses, or other accessories.


The very word “casino” may make most people think of a website rather than a physical venue, these days. And it’s true that digital casinos have carved out a significant amount of business for themselves. Through huge game varieties and no-deposit gaming options for those who don’t feel comfortable gambling online, they’ve expanded their appeal around the globe. This hasn’t actually harmed physical casinos as much as some once assumed it would, however, and particularly in big cities and at major vacation destinations, vibrant, fun-filled venues are still thriving. And rest assured, you can still have a blast dressing up to hang out at these casinos.

Suffice it to say, if you ever admired the fashion choices of Julia Roberts or George Clooney in Ocean’s 11, or Daniel Craig and Eva Green in Casino Royale, you recognize the value of dressing up in beautiful formalwear at a high-end casino.


Weddings may seem obvious, but here too we’re seeing more and more casual attire. Some people will even dare to wear denim to a wedding these days! But for anyone who loves dressing up, most weddings can still be very formal affairs. A little black dress or similar cocktail dress will almost never be out of place, even if you do happen to be in a crowd that’s dressing a bit more simply. And you don’t have to dress it down at all, which is to say there are no concerns about keeping the outfit casual with the right flat shoes, etc. You can wear your tallest heels, carry your prettiest matching clutch bag, rock some statement jewelry, and still fit right in, in the best of ways.

Horse Races

Formal but fun fashion is essentially an imperative if you attend a major horse racing event, like the Kentucky Derby or the Royal Ascot. The former is legendary for its attendees’ gorgeous sundresses and extravagant hats; the latter emphasizes style to the point that it has dress codes for certain areas, and even the British royals show up looking their best. Just make sure you think about all the grass you’ll be walking through, and choose your heels accordingly (stilettos sink into turf with every step). Walk carefully, and try something with a slightly thicker heel to keep you upright.

Otherwise, just have fun with your look! Horse races can embrace the formal (some more than others), but they also invite a certain eccentricity of style. These are the places not just to wear fun, gorgeous dresses (or even try out nice pantsuits), but to wear your boldest accessories, and perhaps try something you wouldn’t try anywhere else.

Most of the above aren’t exactly everyday opportunities. But if you’ve been feeling a certain absence of formal occasions in your life, each of them gives you a perfect excuse to dress your absolute best.

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