The Tomboy's Guide to What to Wear to Weddings

With spring over and summer ramping up into full swing, it’s now officially Wedding Season. For some people, a wedding invitation is a delightful excuse for a trip to the mall – for others, it can be a source of clothing consternation. There are mysterious rules about what you are and aren’t allowed to wear to weddings, and a lot of people who are tomboys or masculine of center in their day to day fashion sense can come under a lot of pressure to pick something more feminine for this special occasion.

Dear tomboys, we’re here to help you say no to wedding outfits that you will spend six uncomfortable hours in and then never wear again. With an understanding of what the traditional “dos” and “do nots” for wedding guest outfits are, you can enter your department store or boutique of choice armed with the knowledge you need to confidently select a wardrobe that makes you feel awesome and that is inscrutable according to the rules of the game.

The 8 Fundamental Wedding Guest Outfit Rules

Here are eight essential rules to remember when figuring out what to wear to a wedding – no matter what anybody else suggests you wear, as long as you follow these guidelines, you’re golden.

1. If you’re not one of the people getting married, don’t wear all white.
2. Similarly, don’t wear all-black, which evokes funerals and death.
3. Read the invitation carefully for clues on the level of expected formality.
4. No jeans, no shorts, no tank tops. No, not even black jeans.
5. Always err on the side of more formal. You can loosen your tie as the night goes on.
6. If you know what color the groomsmen and bridesmaids will be wearing, avoid wearing that.
7. Avoid open-toed shoes like sandals – absolutely do not wear sneakers.
8. The couple are the final law – if they want you to wear a unicorn onesie, that’s what you wear.

Overall Looks You Can Confidently Wear to a Wedding

Bond, Jane Bond: Black Jacket, Black Pants, Black Dress Shoes, Black Tie, White Dress Shirt

You should never wear an all-black suit to a wedding, but as soon as you switch out that dress shirt for a white one instead of a black one, you’ve taken your look from mourning to the classic and ageless “black tie affair” staple. Anybody who tries to give you guff for wearing this has absolutely no ground to stand on.

Something Blue: Dark Blue Jacket, Dark Blue Pants, Dark Brown Dress Shoes, White Dress Shirt, Dark Brown Belt, Blue Tie

Bonus style points if you get the pants and jacket as a matching set so that they’re the exact same shade – you can also select a dark blue with a subtle pinstripe. Feeling extra fancy? Three piece with a matching dark blue vest is a great look. Make sure your socks are also blue, but off by a shade or two. Depending on whether or not your jacket is patterned, your tie can either be solid or patterned, and like the socks should be a shade or two darker or lighter than the rest of the suit.

Summertime Sleek: Camel Chinos, Beige Blazer, Dark Blue Dress Shirt, Light Brown Dress Shoes, Light Brown Belt and Maroon Tie

This is a little more casual of a look, and more likely to utilize items you might already own. You can have some fun with this look while still being in the bounds of appropriate. Just remember this is definitely a spring and summer look, and probably not as suited to fall or winter weddings. For socks, you can nod to either your shirt or your tie with a pair of socks that are navy, maroon, or a pattern that has both.

See My Vest: Patterned Dress Shirt, Charcoal Waistcoat/Vest, Black Necktie, Grey Dress Pants, Dark Brown Dress Shoes

The shirt you wear with this look should be light and have a subtle, classic pattern like stripes or checks. By wearing the waistcoat without a jacket over top, you save yourself the effort of finding the perfect jacket but still utilize some layering to keep things classy. With fewer layers on, you’re also less sweaty in this getup than you would be with the addition of the jacket. Just make sure that your dress shirt fits perfectly, because if it’s loose around the shoulders the vest will accentuate and draw attention to that.

Crafting Your Tomboy Wedding Outfit A La Carte

If you’re not looking to wear a pre-crafted three piece suit, which can be expensive and hard to find in sizing comfortable for women or trans men, you’ll be hitting the stores hoping to piece together your outfit from lucky finds of individual pieces. Just because your sense of style is more masculine doesn’t mean your only option for wedding guest outfits is a suit. Here are some tips for picking out your individual components to your own taste!

Picking A Shirt to Wear to a Wedding

First off, don’t even bother looking at short-sleeved dress shirts. The fact that it has a collar doesn’t make it automatically wedding appropriate – you want to be shopping for something with full length sleeves. Polos and button-up Ts are not the right choice for a wedding.

If you pick a shirt with a dark colour or pattern, you’ll want to make sure you have an accessory like a tie or a pocket square that has a bit more colour to keep things cheerful. If you pick a lighter color, make sure it’s “light” and not “bright”. Weddings are parties but you’ll still want to steer clear of anything that is super vibrant. Blue, purple, green, red, yellow, orange? All perfectly acceptable, as long as it’s a toned-down, subtle version of that color. Think esteemed professor, not Hunger Games host.

Pay attention, if possible, to what color the groomsmen and bridesmaids will be wearing. Definitely do not pick a shirt in a same or similar color. One handy way to avoid doing this accidentally, especially if you have no intel on what they’ll be wearing, is to go with a pattern instead of a solid color. Obviously you’ll want to avoid garish patterns that make you look like a tourist on a beachfront, but weddings are a great place for a subtle plaid, paisley, dots or stripes. If you wear a vest or jacket with this shirt, it’ll make it easier for you to coordinate if the vest/jacket are solid to provide some grounding for the fun pattern of your shirt.

Picking a Waistcoat or Vest to Wear to a Wedding

Investing in a nice, sharp-looking vest for a wedding can pay off in the long run, because this is definitely an item you can put to use long after the wedding is over. Adding a vest to a jeans and button-up outfit is an instant bump up in style and classiness without much effort at all.

If you’re wearing the vest with a suit, you should make sure it matches or is in the same color family as the suit jacket and pants – beige with beige, black with black, blue with blue, and grey with grey. If it’s a solo piece, think more about the dress shirt you’ll be wearing it with. A nice charcoal grey vest is a really good choice because it’s more relaxed than a black vest but easier to pair with different pieces than a blue or a brown would be. If you wear the vest without any jacket, you especially want to avoid wearing a black vest with a black tie, which makes you look more like an employee at the venue than a guest at the party.

Don’t be afraid to take your new vest to a tailor if you buy one off the rack – a truly flattering waistcoat or vest requires a slightly snug fit that sits on you in a way that isn’t button-popping tight but isn’t baggy or loose in any spots. If the store doesn’t have one that’s perfect, lean towards the slightly loose one and then invest the $10 - $20 to get it professionally taken in.

Picking Bottoms to Wear to a Wedding

Unless you’re the kind of tomboy to likes to rock a skirt, you’ll be looking for full length dress pants. In a spring or summer wedding you can get away with a light color like beige or a light grey. If you are going lighter, definitely lean towards an earth tone or a light grey, because something like a baby blue or a pale green is going to be harder for you to create a cohesive and classy outfit around, and will see less use after the wedding is over. Even in summer, it’s best to avoid wearing white pants to a wedding.

The easy pick is a pair of black dress pants or a pair of dark blue dress pants. The black pants will go well with a black belt, black leather or vegan leather shoes, and a wide array of dress shirts. The blue pants can be paired perfectly with dark brown leather or vegan leather shoes and a matching dark brown belt, and will look especially good with striped and checked shirts.

Picking a Tie to Wear to a Wedding

For neckties, you’ll want to stick to either a solid color or a more traditional pattern like stripes or dots. An easy tie selection guideline to remember is that your tie should always be darker than your shirt. Avoid graphic neckties, unless the graphic is so subtle as to look like a traditional pattern from a distance – for example, a dark blue necktie with tiny baby blue sailboats that look like dots until you get close. Since it’s hard to find “fun” ties that do a good job of straddling the two worlds of formal tie and goofy tie, it’s probably easier not to get your heart set on it.

Bowties, on the other hand, can be much more fun. Because they take up less visual real estate on your outfit, you can be a little more playful with them, as long as the colors in the bowtie match nicely with the rest of your outfit. A good contrasting bowtie can be a fun pop of aesthetic variety on an otherwise monotone ensemble, or else they can act as the classy solid-color piece that brings it all together with that elegant little detail.

A note on white ties: they can look super sleek with an outfit like the Bond, Jane Bond, but you may buy one and then never wear it again. White neckties are such a niche item that they just look out of place at job interviews and office meetings, especially because they really only look good with an all-white suit or a black suit with a white dress shirt. It’s appropriate to wear to a wedding with the right look, but you likely will never find another opportunity to make use of it.

Picking Shoes to Wear to a Wedding

If it’s a formal wedding, especially “black tie” formal, you’ll want a pair of black lace-up oxfords or derbies. Avoid heavily brogue patterned shoes for these kinds of super formal wedding settings. You’ll also want to avoid loafer style shoes for this level of formality.

For dress codes that aren’t so explicitly high formality, you can rock either black lace-up dress shoes or dark brown lace-up dress shoes without any hesitation. Some classy brogue medallion detailing is totally acceptable for the average wedding dress code.

The less formal things get, the more leeway you’ll have. For an outdoor wedding or a beach wedding, you can start feeling secure in selecting a light brown shoe or a heavily brogue patterned shoe, as well as a loafer style pair of shoes if you like.

At most weddings, you’ll want to avoid doing anything too wacky like wearing colored shoelaces with black or brown shoes.

If the shoes you wear are a pair you’ve owned for a while, give them a little TLC on the morning of the wedding – gently wipe them down with a damp paper towel, pat them dry, and then give them a good polish. You should be doing that regularly anyways, but that day-of shining will add just that extra bit of sophistication to your look.

Under no circumstances should you ever wear sneakers or flip-flops to a wedding. Just don’t do it!

Some Miscellaneous Tips

If you’re wearing a jacket that has buttons low on the midsection, you’ll want to button them fully while standing, and unbutton them when you sit.

When selecting a belt, make sure it matches your shoes; the easiest way to be sure you’ve picked the right belt is to select the same shade and glossiness of leather or vegan leather that your shoes will be.

Not sure what socks to wear? The shortcut is to choose socks the same shade as your pants.

As a rule, avoid mixing black and brown together in an outfit.

Remember, it's a party! Have fun!