How to Look Your Best At the 2025 AF Gala

So you’re headed to the AF Gala this month and have nothing to wear. Well, consider yourself lucky because for men, the outfit of choice for such an event has remained unchanged for well over 100 years.

By selecting something classical, you could play it safe and dress like your great-grandfather. Classical attire includes a one-button black tuxedo and the all too standard black bow tie and cummerbund. Don’t forget the studs and cufflinks. But this is the 21st century, and we’re all about maximizing liberty and individualism, which is why the dress code for the AF Gala is “creative black tie“ with a theme, “Party Like It’s 1995”. Did people even wear tuxes in ‘95 or was it all grunge and 70’s throwbacks? Regardless, we’re here to help.

However, there is a difference between dressing up and dressing well. For a social evening like this–you know, one of the best parties of the year–dressing just one step above the rest will get you noticed and leave the right impression.

Below, I breakdown the different parts of your ensemble for the evening in three levels: classical, modern, and dandy. This guidance is merely a framework for basic formal wear, while also allowing one to “peacock” with options to help you stand out in a crowd. Proceed at your own risk.

At the end I also give a quick rundown on garment fit, because a $100 suit that fits well will always look better than a $1000 suit that doesn’t.

Jackets
Classical: Black one-button jacket with satin notched lapels
Modern: Black or colored jacket with satin peaked or shawl lapels
Dandy: Colored jacket with exquisite pattern or a fabric like suede
No-Fly Zone: Tan and khaki jackets of any kind. The Kentucky Derby has passed, and we don’t want to revisit President Barack Obama in the briefing room circa 2014. It’s been a decade and GQ is still giving him hell for that suit. British tail jackets are acceptable…if you’re British.

Trousers (I think they call them slacks or dress pants today)
Classical: Black, relaxed fit, pleated with satin stripe down the side
Modern: Black or colored, slim fit, flat front, without the satin stripe, and tapered ankle opening (usually with no socks)
Dandy: Any color contrasting the jacket or patterned pants
No-Fly Zone: Leather/Latex. This is best left for aging rockstars and… Other purposes.

Photo: Ralph Schulz

Shirts
Classical: White, wing collar, with pleats
Modern: Forward point or spread collar with no pleats
Dandy: Colored or patterned shirt with spread collar
No-Fly Zone: Black shirts of any kind. Leave your heart of darkness for metal concerts.

Neckwear
Classical: Black silk bow tie (preferably not pre-tied)
Modern: Tuxedo ties and patterned bow ties 
Dandy: Ascots/cravats
No-Fly Zone: White ties or no neckwear

Shoes
Classical: Black, shiny, round toe Oxford
Modern: Slim Italian/Spanish pointed toe black Oxford or Spectator shoe
Dandy: Colored velvet slipper
No-Fly Zone: Sneakers. Chuck Taylors are for basketball, and Vans are for skateboarding.

Socks
Classical: Black (made of silk)
Modern: Color-matched to vest, bowtie, or other accent piece
Dandy: Colored, patterned socks or no socks
No-Fly Zone: White socks are for the gym and 1980s NBA players. Actually, no – they belong in the garbage, especially those ones with the double stripes.

Belts
If you are wearing a belt, you are not wearing a tuxedo.

Braces/Suspenders
Unless your pants constantly fall down, there is no need for braces (which button on the inside of your pants). Suspenders that clip onto the outside of your pants are best left for connecting to your jeans back home on the ranch or as a uniform for your early 2000’s soft emo boy band.

Underwear
You’re on your own here. My recommendation? Wear some. The same goes for undershirts. I will admit, once upon a time, I got fat and had to go commando to get my tux pants to button. It happens.

Accessories
Classical: White pocket square, basic studs, and cufflinks
Modern: Patterned pocket square

Dandy: Pocket watch tucked into a vest or boutonniere/lapel flower
No-Fly Zone: Canes (unless you are a pimp), top hats (unless you are Abraham Lincoln), and necklaces (unless you are a rapper). Hint: you are none of the above.

90’s Add-Ons (New for this year!)
I’ll admit, Robert and I were not focused on style in the mid-90’s. He was still being dressed by his parents and I was busy being born. That being said, we’ve both learned about the trends of the 90’s after the fact and agree that chunky/platform shoes, choker necklaces (for the ladies), and rave accessories like boas and glow sticks definitely had their moment and would be great to incorporate into your AF Gala outfit.

Garment Fit
One hundred years ago, men were pretty much all the same size and fit. That’s why in 1901, Brooks Brothers came out with the No. 1 Sack Suit, the nation’s first ready-made garment for the (traveling) man that was too busy to get fitted for a custom suit. Today, men come in all shapes and sizes. The retail and rental industry is having the same problem as a politician: trying to be all things to all people. From no butts and beer bellies to the CrossFit hourglass shape, it can be hard to find clothes that fit well in your day-to-day wardrobe, much less for important events. Most of us don’t have the money for a custom tuxedo and will likely be renting. While no garment will fit perfectly, there are some aspects that will completely change the way you look and feel, which will make all the difference.

Starting at the top, make sure you have plenty of neck room(1-2 fingers) in the shirt collar or you’ll be miserable all evening. Second, ensure both the dress shirt and the jacket aren’t “eating” your hands. Both the shirt and jacket sleeves should come down to the break in the wrist and should not touch any part of the palm. Ideally, you shouldn’t be swimming in the body of the jacket, but depending on proportions, this may be hard to control.

If you’re renting pants, get the smallest adjustable size possible. Pants that adjust from 32-42 in the waist will end up looking like Humpty Dumpty pants on a trim man. Make sure your pants have a half or a full break on top of your shoes. While I don’t encourage “short pants” that look like PeeWee Herman, that’s better than having “puddling” pants that are several inches too long.

Ladies, fit is generally not an issue on your side of the equation. The 90’s embraced low rise pants and baggier clothing overall, but for a gala, you’ve probably got your dress ready to go. Just remember that there’s a difference between a cocktail dress and a gala dress. You may attract attention in both, but you should discern the motivation accordingly.

A final rule of thumb for all your clothing: vertical lines in the garment means that it is too loose, and horizontal lines mean it’s too tight. May the fit be with you.

Alright superstar, I’ve done all I can, and now it’s up to you to make it happen.

 

Editor’s Note: This post was written in 2021 and updated for the 2025 AF Gala. Have you gotten your tickets yet? Don’t miss this must-attend event! 

This post was written by Anthony Bolognese and Robert Ordway, their bios are below.

 

Anthony Bolognese is a dynamic entrepreneur and founder of Capitol Hill Clothiers and Capitol Hill Photo. He also holds investment stakes in Carbonara Old School Italian, The Brig Cigar Lounge, HYDE Social, and serves as a managing partner of Capitol Hill Tobacco Company. Anthony’s work has earned him features in prestigious publications such as Rolling Stone, Washingtonian, DC Modern Luxury and Famous DC. He has captured iconic images of celebrities like Adam Driver and Tom Hanks and designed one-of-a-kind suits for Washington’s elite. He also premiered just this past Sunday in Season 14 of The Blox, a competitive entrepreneurship reality show. In addition to his own pursuits, Anthony offers business consultation to business owners and aspiring entrepreneurs. He loves cigars, whiskey, fine clothing, heavy metal, and tattoos.

 

 

 

Robert Ordway is a Senior Policy Advisor for Indiana Governor Mike Braun. He owns Rusted Oak, an image consulting company, formerly a menswear retail store. He got his start in menswear at both Brooks Brothers and JCrew. He became a certified custom clothier in 2015 and has served as the Board Secretary for the Custom Tailors & Designers Association (CTDA) in New York City since 2022.