Preparing for homecoming can be a very complicated and nerve-wrecking experience for almost every teenager (and their parents as well, if they’re assisting with the shopping). But the key to reaching a slick and elegant look which is cool at the same time is looking like you didn’t try too hard, wearing much too grown-up clothes. One of the best ways of looking awesome and composed but not like you over-tried is to combine elegant elements with some touches of a more casual or relaxed style. For men’s style, a high-quality, leather look messenger bag may be just the cute detail that takes your whole suit outfit into an elegant yet casual and relaxed look. You can even call it sport-elegant. 

Here are a few tips for sporting a leather messenger bag to the prom, in various styles, depending on how the rest of your outfit looks like.

1. Match your shoes with your blazer, and wear casual pants

Wearing suit pants and a suit top and a shirt and the whole package is a bit too much and you may end up looking like an overdressed and pretentious, clueless guy. Tone down the formality and choose casual pants instead. Make sure the blazer or suit top is matching your shoes and not your pants. March a leather messenger bag to the whole thing at it will look sleek, business-casual. 

2. If you’re wearing the whole suit, choose a business-style messenger bag

If you have a particularly good look already composed and you do choose to wear the whole suit pack after all, then you need to pick a business type of messenger bag to match it but also balance it out. Make sure that you at least alternate dark and light colors in the overall composition (while keeping the bag and the shoes dark-toned). 

3. Wear a ¾ sleeve white shirt with a dark blazer and black tight jeans

Another good idea for a smart-casual look which you can take to the prom is wearing a ¾ sleeve white shirt (classic, yet a bit more relaxed) with black jeans, more towards a skinny type of fit (if it’s flattering to your build). Match it with a dark blazer (not necessarily black also, perhaps a dark blue or dark green) and a black or very dark brown messenger bag. The trick is not to have the bag be too brown, as that you totally not match the rest of the outfit, but not too pitch black either. 

4. Match oversized geek glasses with a pastel colored shirt and suit

You can just combine a light yellow with light blue and your oversized black glasses and you’d have a killer look, reminiscent of Mr. Gustave from The Grand Budapest Hotel. Well, to be fair, the pastels are more about the style of Wes Anderson movies per se, than the style of Mr. Gustave, but you know what we mean. You may think pastels are too daring for guys, but don’t worry: you will look so fresh and smart-casual you won’t believe it. A canvas messenger bag is more suited to this look than a leather one.