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How to Dress for a Date at a Cocktail Bar


ressing up for a date may stress you out, it can be difficult because you want to get a good impression, it may be your first or third date. To leave a nice picture of a date to the woman you like, there is one of the important key-points, and that is your clothes.

You must accord yourself with the setup of the date you will be having. Of course, we don’t want to underdress nor overdress.

If you are going to a fancy restaurant, a cocktail bar or to the theater, best to opt for the cocktail attire. Dress like a man. Dressing well is also a way of telling your date that you take her seriously.

As for the cocktail bar set up, the ones who are making the drinks are well dressed so you might feel intimidated once you step in. But this kind of bar is really a great place to take your date and have some fancy drinks. You better dress up, or should I say suit up!

Cocktail Attire for Men

Cocktail attire has been a staple in social gatherings and events since the ’20s. It’s a semi-formal kind of clothing, or now we say a dress code, for the ladies as well as the gentlemen. Nowadays, styling cocktail attire has a modern twist but still has the essence of formality in it. Dressing up a cocktail attire is a little tricky, you would like to look smart and sleek but maybe you will end up looking like an office guy or a businessman. This attire is really far from a street or your go-to style, yet it’s also a level under the formal attire, not like the tux.


Suits are much better if they are tailored, a well-fitted suit will be perfect to wear as a cocktail looks, cocktail suits should not be too tight. You can also shop off the rack as long as it has good cut and fit. Semi-Formal blazers and smart pants or chinos are also good to use as an alternative.

Darker colored suits are worn traditionally as a cocktail attire, keeping it classic and manly, you may choose navy, black or gray suits, these colors are great for all seasons. Bolder prints would look great too. Don’t wear such patterns that would make others looking at you dizzy, better to avoid pinstripes and choose a windowpane or herringbone.

Suit Supply, $599

Suit Supply, $499

Suit Supply, $499


Shirts under the suit should not be too over the top, so keep it basic, opt for white, light blue or muted gray. Patterned shirts can create a chic look, which is best matched with the set up in the cocktail bar, but make sure that the shirt won’t stand out too much. Your shirt must match well with the color of your suit, they should have complementary shade to make a good combination.


George Cleverley, $750

Gucci, $650

John Lobb, $1,480

Paul Smith, $495

Cocktail attire is not complete without a great pair of shoes, this part of the outfit must not be overlooked. Authentic leathers with an additional texture like a classic brogue will rock this look. Since cocktail bars are less formal, wear a pair of brown dress shoes or loafers, or simply wear black shoes, they will make your total look macho. Brogue with a beautifully designed platina can make your outfit garb.

Ties and Pocket Squares

Ties have been an accessory for creating a formal and respectable look. Choose a classic cut of a tie with nice color as well as texture. Look for a tie with a stylish weave or a crochet one. Palpable colored and patterned ties are also acceptable as long as you jacket has a calm color. It’s actually fine not to wear a tie, just unbutton a few buttons and you will have a relaxed look.

Pocket Squares gives the attire a more stylish touch and classic look. If you wish to wear a pocket square for a cocktail bar set up, I suggest to go for a casual style and that is the four peaks pocket square fold.

Tie Bar, $19

Tie Bar, $10

Tie bar, $19

Tie bar, $10


Invest in a good-quality belt that is well-designed for a cocktail attire. One rule that you always keep in mind, the belt must match with your shoes. As what has been mentioned above, you would wear a pair of brown shoes so better to opt for a leather or suede belt, these materials can last longer.

Wacthes for the cocktail attire must look elegant which means no cloth, leather, and colorful straps. Brushed metal straps like gold and silver go well with the outfit, I prefer to wear a silver watch with lesser details to keep it simple but elegant. And for your tie bar and other accessories, match them with the color of your watch.

Keep your ankle from showing off by wearing a pair of calf-length socks. The socks they should be a shade lighter or darker from the color of your pants. If you are into a sartorial style, choose the socks that match with your tie or pocket square.

Add up a fedora hat to your outfit, this will bring out a gentleman aura and of course this is the cherry on top.

Smelling good also brings out confidence, your scent is important in a date and it will add masculinity to your attire. Use a fresh scent which is just simple and basic but still memorable.

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