Look, weddings are fun. You get to hang out with some of your best friends. Most of the time, you get an excuse to spend a night in a hotel. Sometimes they have photobooths and other times they have disposable cameras. It’s mandatory for weddings to have cake, which is always a plus. And the best weddings have an open bar.
With all of that, it can still be a stressful time to find the right outfit. After a couple of years of being locked down, masked up, and working from home, many of us lost our mojo for dressing up. Thankfully, you have me. I’ve broken down the four most common degrees of formality for weddings and provided a few staples in each category for shirt, suit, shoes, and accessories.
The key is keeping it simple and buying a few versatile pieces, so take these suggestions, mix and match, and have fun.
Now onto the next thing to worry about: what’s your karaoke song at the reception?
What to Wear to a Casual Wedding
Casual wedding attire has become more and more popular with the advent of the COVID-19 pandemic, when many of the rules around formality were thrown out the window in response to the disarray of the world around us. Casual doesn’t mean shlubby though. Make sure that you are putting in the effort. While tailoring may not be as important as comfort, the outfit itself should indicate some form of prior planning. You can go with a comfortable shirt (make sure it’s collared – no t-shirts here, folks!) and then round out the outfit from there to match the general occasion. Clean sneakers never go out of style, and a chino you can wear to work the next week gives you more bang for your buck. I’d go without a tie for anything casual – it’ll make the other partygoers unsure if they’re underdressed or worse, that you’re overdressed.
Shirt: Banana Republic Castello Linen Shirt
Now that we’re settling into summer, it’s best to keep it light and breezy. I almost exclusively wear linen when I’m doing anything that involves “dressing up” a bit, and that includes the casual wedding here and there. I’m thinking beach wedding vibes in this shirt. Open the buttons on the chest a little and have the sleeves rolled up ¾ length for that extra little sprezzatura look.
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Pants: Flint and Tinder 365 Pant
Since this is a casual affair, we’re opting out of a suit, but instead going for well-structured pants to contrast the more urbane shirt choice above. These pants by Flint and Tinder provide quality craftsmanship that can double as your daily work pant once the festivities are over.
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Shoes: Birkenstocks Arizona
I previously wrote about dress shoes and I was tempted to include Birkenstocks, but I didn’t want to be canceled. It’s a risky inclusion for sure. But I think if the time and place call for it, a classic Arizona can be the best shoe to stay comfortable on the dance floor all night long.
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Accessories: Tomahawk Lumbergs Sunglasses
Eschewing a tie for another accessory, we have a great pair of sunglasses that are a little bit 70s but with modern updates to the silhouette and color choice. Tomahawk makes some great styles, so if you think you can’t pull these off, take a look around – you’ll find something to complete that Casual Wedding vibe.
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What to Wear to a Semi-Formal Wedding
Semi-formal will mimic the everyday attire you may have for your office. It’s relaxed, yes, but that doesn’t mean it doesn’t have the same bit of dressing-up one would expect from something as big as a wedding. Keep it simple with the same blueprint as anything more formal: shirt, tie, suit or jacket, and some good shoes. With this in mind, you can make the style your own by playing with the fit (such relaxing the shoulders), colors, or even materials, like a nice linen. As long as you put in the effort and wear a jacket, it’s semi-formal in my book.
Shirt: J. Crew Broken-in Oxford
Few items are more of a staple in a men’s wardrobe than an Oxford. I quite like the broken-in option from J. Crew, which removed the stuffiness (and stiffness) that one finds from other retailers. Go for white and add it to your streetwear rotation. It’s easy to find ways to wear an Oxford after the wedding.
Buy Now $80
Suit: J. Crew Ludlow Unstructured Cotton-Linen Suit
J. Crew’s unstructured suit is an incredible option at an incredible price point. I’d go for grey myself, but the navy will get you through many weddings without the risk of sweat showing through. J. Crew’s suiting sizes are pretty true to standard, which makes taking the guesswork out of buying that much easier (though, if you’re asking me, I always recommend a tailor, too). Not only that, but the unstructured, unpadded frame gives it a relaxed feel that can be worn in countless permutations throughout the year.
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Shoes: Savannah Tan Sabah
It’s no secret by now that I’m a bit of a fan of Sabahs. But it’s for two very good reasons: their quality is unmatched and they go with anything. With a white shirt and a navy suit, I’m thinking a pair of Savannah Tan Sabahs finish off the outfit with a bit of polish without any of the stuffiness of a typical, say, brogue. Go sockless, embrace the ankle, and enjoy the night looking sharp AF.
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Accessories: Reiss Barrow Linen Tie
With this look, you can go without a tie or you can get a linen one from Reiss. I’d go for the latter. Their pink tie adds the slightest bit of color and the linen offers a soft palette that blends expertly into the Ludlow, making it feel like an intentional look and not, well, just a tie you found in the back of your closet.
Buy Now $75
What to Wear to a Formal Wedding
Here the rules become a bit more solidified and you reach the territory of proper dressing-up. The blueprint stays the same as the above, but fits and patterns become a little more restrictive in choices. Keep it simple. The worst thing you can do is go to a wedding and take attention away from the groom. If you invest in quality, you can get away with wearing the same suit and oxford over and over again all year long. Stick with navy or black in a rugged material that can withstand a few wears between dry-cleaning and find a matching shoe in a more vibrant neutral, like a chocolatey brown or a nice rich tan, to give the slightest pop to your otherwise monochromatic outfit. The tie is another place where you can be playful. I personally like to go with a vintage designer, but you do you.
Shirt: Drake’s White Oxford
Another occasion, another Oxford. While the above option from J. Crew is a dream, you won’t want to wear it to another formal. It’s a little too broken in. Drake’s has the answer with their own shirting. Crisp in a traditional cut, this Oxford sets the tone for the occasion while being a blank canvas to dress up.
Buy Now $255
Suit: Drake’s Navy Tropical Merino Wool Jacket and Pants
The priciest option on the list, Drake’s Tropical Merino Wool suit will last you years if you take care of it. It’s made of a twisted merino wool with an unlined construction to get the lightest, most comfortable fit possible. The single-pleat pants are a subtle upgrade to a traditional flat–front that gives a classic, but not boring, aesthetic to the look.
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Shoes: Amberjack The Original
The shoes here are ones that you can wear outside of a suit and won’t break the bank (assuming you’ll be buying the Drake’s suit, I thought I’d give you a deal here). Amberjack’s Original has athletic upgrades like arch support and outsoles while giving us a very traditional shoe that can be worn for nearly anything you have going on.
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Accessories: Hermes Tie
Against the canvas of the crisp oxford should lie a beautiful tie, don’t you agree? I’m going all out and considering an Hermes tie for this option. There is a great resale market for Hermes (The Real Real has some for $20!), but if you’re looking for new ones, go with the Pied Marin series, which is an overlapping fishscale pattern with anchors as the motif. It’s classic and, being so bold, almost acts as a neutral. And like anything with this brand, it’s ageless, so you’ll get your miles out of the $215 price tag.
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What to Wear to a Black Tie Wedding
This option has the least amount of guesswork, which can make it hard to mess up. Hint: tuxedo. That’s the main takeaway. But the devil is in the details here. Black tie comes with a pretty rigid set of rules that are hard to deviate from without looking a bit silly. To make it really your own, you’ll want to look for slight variances in fit and fabric, looking for designers who mimic your personal taste in color and fabric choices. A tuxedo also means a special shirt is needed (an Oxford won’t do) and a bowtie always looks classic here. Add small details like a pocket square, cufflinks, and minimal jewelry to stand out in the crowd – getting dressed up is, as we know, half of the fun of weddings.
Shirt: Proper Cloth Stanton 120s White Broadcloth Tuxedo Shirt
A classic tuxedo shirt is hard to find and many a man has made the faux-pas of wearing a (gasp) regular white dress shirt under their tux. You need a tuxedo shirt if you’re wearing a tux. A plain front, like the one from Proper Cloth, gives you the versatility you may need for any other upcoming events.
Buy Now $130
Suit: Todd Snyder Sutton Peak Lapel Tuxedo
The reigning king of American prep (sorry Ralph!) Todd Snyder had to make an appearance on this list somewhere. I was pleasantly surprised to see he had a tuxedo in his collection that was, even more surprising, at a fairly reasonable price. Slim-cut in a wool flannel, break this puppy out for those black tie affairs where you want to look as good as you feel.
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Shoes: Stubbs & Wootton Black Private Stock
Stubbs & Wootton is my favorite black tie brand that’s not a traditional option for many. Their Private Stock loafers are hand-crafted with a velvet upper and a wooden heel. They’re luxurious and just a tad decadent, but really – what’s wrong with that?
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Accessories: Hugo Boss Silk Bowtie and Cad & The Dandy Pocket Square
To complete the look, go for two items: a bowtie and a pocket square. I like Boss’s bowtie for its simplicity and the silk which has an almost jacquard texture to it. I also opted for a Savile-row tailor Cad & The Dandy’s white silk pocket square to ensure that the very last detail is accounted for.
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