Awards season may help you figure out what you should be watching, but it also provides a great deal of inspiration for what you should be wearing—with stars pulling out all of the sartorial stops for awards ceremony after awards ceremony. With the end of the season marked by tonight’s 89th Academy Awards, we sat down with menswear expert Brian Sacawa, the voice behind the extremely successful menswear blog He Spoke Style, to filter through the best—and worst—ways to approach eveningwear. Here are his top tips for modern men dressing for black-tie occasions.
Robb Report: What is the most important thing to keep in mind when dressing for formal occasions?
Brian Sacawa: If you dress conservatively and classically, unless your fit is just perfect, it can look terrible. Because everyone is so different, it is really hard to get a perfect fit off the rack. When you are buying off the rack, the patterns are not cut for you—they are cut for tons of people. So you should have a relationship with a tailor, and should know what looks best for your body type. I always prefer to have my suits made, either custom or made-to-measure—that way you know you are getting a fit that is absolutely perfect for your body.
RR: How do you take a sartorial risk when the dress code calls for black tie?
BS: I think one of the biggest mistakes men make when it comes to showing their personal style in general is trying too hard. To me, a perfectly fitting suit or tuxedo will make a much bigger statement than if you are wearing a loud blazer or some kind of funky tie. One really easy way to look very sophisticated but do something a little bit different is to wear a turtleneck with your suit. Another thing you could do is wear a velvet blazer in dark brown, black, navy, [or even] a really dark hunter green.
RR: How can you use accessories to liven up a traditional tuxedo?
BS: Wear cufflinks, but don’t wear novelty cufflinks. [They] are a great way to show some personality, but if it is a black-tie event, just keep them simple. Alexander McQueen and Paul Smith (shown, $150) make some really cool cufflinks, but they are [also] really subtle and subdued. From afar, [they] look like regular gold or silver cufflinks, but when you look closer [they are] actually a skull or a bicycle wheel. Cufflinks are a good way to add a little personality [to a tuxedo] and take a little bit of a risk.
RR: What are your go-to shoes for formal occasions?
BS: The velvet slipper is something that, like a cufflink, you can show a little bit of personality with. You could have a monogram or make some type of a statement with them. Del Toro’s [embroidered velvet slippers] are fantastic.
RR: What common mistake do you see men making when the dress code calls for black tie?
BS: Don’t wear a watch. This is kind of an old-school way of thinking, but for me a tuxedo is very stark in a way, and it’s very simple. If you have it tailored right, the lines look perfect, and a watch can distract from that—even if it isn’t a flashy [one]. Also, if you are going to an event that is [extremely] fancy, having a watch on is almost disrespectful [because it shows the host that] you are concerned with the time. If you are going to this really fancy party, you shouldn’t be concerned with the time or when you have to leave.
RR: Which celebrity do you look toward for inspiration when dressing for a black-tie event?
BS: Donald Glover is a good example of someone who keeps it classic, but is a little bit more adventurous. At the Golden Globes he wore this brown velvet tuxedo with a purplish [bow] tie, and he can pull that off. The thing to remember is that if you feel it, and if you can own it, then you should go for it. If you are at all uncomfortable with going out on a limb [with what you are wearing], don’t do it because people will be able to see [your self-consciousness.] (Items pictured available via tomford.com, paulsmith.co.uk, and mrporter.com)