Jovan
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I've seen so much misinformation on renting dinner jackets thrown around by certain rental companies (After Hours, most notably) and people who don't know what they're talking about that I was compelled to write my own, real guide on how to dress well for prom and still look classic, but cool. Here it is.
So you want to rent, eh? Most of you will have to, given your budget or lack of decent hand-me-down dinner jackets (what Americans call a "tuxedo"). And for God's sake, if there's one from the family or thrift shop that fits you fine, use it instead and scour around for any accessories you may need. But if you must rent, here's a few things you need to look for:
1. Price. And not just what they tell you at first, what it all comes down to even after you get a "good deal" with a coupon. Ask them what it's all going to be BEFORE saying you'll take it. Confirm all the details you want. Make sure there's no hidden fees or anything. After Hours is notorious for pulling these sorts of things.
2. Sizing. While it may seem obvious, it isn't always. Some places that rent will only give you the closest size. So if you're a lean 37" chest, some places will only have 40 and above to rent. Again, ask before.
3. Fit. This also may seem obvious, but not always to an untrained eye. Check to see if your sleeves end at your wristbone. You may have to compromise here, as most rental places won't take in the sleeves if they're too long. However, just make sure they don't come down to your thumb. Places will automatically give you a Tall jacket if you're 6' and above most times. But this isn't always accurate, as torsos and arms can be wildly different in length. To avoid this, tell them to take your arm length into account when choosing the right length of jacket. I'm 6' but most times get a Regular. You'll know you have a perfect fit if your shirt cuffs show about 1/4"-1/2" out of the jacket sleeve. Make sure your trousers only break (gather on top of the front of the shoe) a bit, and that there's no bagginess at the heel of your shoe. Otherwise, it will look sloppy. If you spot any, make sure your trousers are pulled up to your navel and then ask them to re-hem them higher if there's still a problem. And yes, I said your navel. You can't wear these like your low rise jeans or Phat Farms, guys. Don't be an Erkel, though. Your "boys" should still be comfortable. Shirts aren't rocket science. You won't get a very fitted one, but the collar size and sleeve length should be right, and that's hard to get wrong. If in doubt, the cuff shouldn't move any or very much when you bend your elbow 90 degrees. The collar should be snug, but neither constricting nor loose. You should be able to fit two fingers between your neck and it with ease.
Now we need to move on to styles, which can be very tricky.
Jackets: You'll get many choices here. I'm going to be quite firm here when I say stick to a regular jacket or tails (those jackets that are short in front, but have long "tails" in back, like you associate with penguins). Trust me, you'll look back on your pictures years from now and wonder what the hell you were thinking if you choose that full length Matrix coat with satin lapels. Stick to classic choices here -- one button single breasted or 4x1 (four buttons, one to close) double breasted, peak or shawl lapels. Notch lapels are a no-no, as they LOOK like a cheap rental. Do NOT get single breasted jackets with two or more buttons. If you want to wear a business suit, this isn't the time. Similarly, don't get a million buttons on a double breasted. Keep it simple. Make sure the jackets don't have a vent in back (this is traditional, and again keeps it from looking like another business suit) and that if there's any pocket flaps, you tuck them in. Traditional dinner jackets shouldn't have pocket flaps. Always remember -- the simpler the jacket, the more formal it looks. Tails will usually be in only one style, peaked lapel.
Trousers: You won't get many options here usually. At most, pleated or not. If you like flat fronts and they're available, go for it. It doesn't make a difference in how formal it looks, just a matter of preference. Pleats will give you a bit more movement room; that's what they're designed for!
Shirt: There will be a few styles here. Make sure it's a white one with French cuffs. Collar styles should be limited to wing or regular. There should also be a pleated or pique "bib" on the front. Pique (said "peek-ay") is a textured fabric. Here's where it gets complicated. A regular collar should be worn with a regular dinner jacket. Wing collars are fine with this, but better suited to be worn with tails. In fact, wing collar is the ONLY type to be worn with tails. Pleated or pique front is fine for a dinner jacket, but pique should always be worn with tails.
Bow tie: I only advise bow ties with evening wear, because it lends better formality and is, again, the classic choice. Unfortunately, no rental places seem to carry self-tie ones anymore. But keeping this in mind, make sure you get a solid coloured bow tie in black satin for a dinner jacket (regardless of waistcoat colour, it looks better contrasted), or white pique for tails. If you do somehow come across a self-tie one, look up how to tie it online. It will take a bit of practice, but it's well worth it.
Waistcoat: Or known as a vest. Get one with 5 or 6 buttons in black or white satin or the same fabric as the jacket/trousers (if they have that, make sure it's black). Don't give into the hype about matching your date, it's really not required and pretty tacky. Leave it to the boutonniere and corsage to match. If you somehow find a waistcoat with three or four buttons, it's something worth considering, as long as it isn't in white pique fabric. That's reserved, again, for tails.
Cummerbund: These are a good choice, too. Not everyone likes them, but they're cooler to wear (more on that later) than a waistcoat. Make sure it's in black satin and that the pleats face upwards when you put it on. It's also simpler to put on than buttoning up a waistcoat and adjusting the back strap. You should never wear one in place of a waistcoat with tails.
Shoes: "Oxford" style in patent leather with plain toes, black. Simple enough, eh?
Cufflinks/studs: Black or white for dinner jackets, white only for tails. Make sure they're silver and not gold, which will look really out of place.
So, going on to styles...
Black tie, or semi-formal: Black dinner jacket with matching trousers and bow tie with waistcoat or cummerbund. Pretty much the rules you just read here apply, obviously. The black dinner jacket can be substituted for a white one, usually without satin lapels, but keeping the black trousers. This stems from the old rule about it being an option in warmer climates or summer. This look is quite suave, like James Bond in Goldfinger. If it's warm out, you can also just ditch a waistcoat or cummerbund completely with either jacket. A lot of die hard traditionalists will curse me for saying it, but I think it looks fine without either. Your comfort is paramount. Additionally, if you went for a double breasted jacket, a waistcoat or cummerbund isn't needed or expected by pretty much anyone. Just make sure you keep the jacket buttoned -- nothing looks worse than an unfastened double breasted flopping around. You can leave a one button jacket undone and it'll look fine, however. It's not required to wear studs on the front of your shirt with black tie, and most rental shirts are convertible to use either buttons or studs.
White tie, or formal: Tail coat with pique wing collar shirt, white pique waistcoat and bow tie. You have much less freedom here, and should always wear the waistcoat. Studs should always be worn, too. Technically a prom is a formal dance, so this is the classic choice. I don't see anything wrong with either mode of dress though. White tie is something nice to treat yourself with if you're feeling bold, like I did. However, it is much warmer to wear than a white dinner jacket with no waistcoat/cummerbund as discussed before. Weigh your options.
Finishing touches: Finish with a classic boutonniere for yourself and corsage for her. Red or pink roses always look wonderful. The florist should be able to help a great deal. Be sure your outfit is pressed and clean, and that you're well groomed. Have fun!