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How To Plan An LGBTQ+ Wedding (Part 3: Fashion Guide)

Chicago’s wedding industry pros weigh in with advice on how to put your best foot forward on the big day—and how to gain confidence from the clothes on your back.

By Elise Hofer Shaw

There are many special moments to consider stacking up for your wedding day, and your fashion moment can be one of them. After all, there are those photos to think about. But beyond that, what you wear on your big day can be a powerful thing. A handsome suit or a gorgeous gown is a wonderful way to show your partner how happy you are to be getting hitched—and that showing up (with a glow up) wasn’t even a question. Your chosen wedding garb can also give you the confidence you need to be the star of the show—and face some relatives you might not be so keen on rubbing elbows with. Thus, if a sartorial statement is important to you and your partner, be it traditional or avant-garde, Chicago’s wedding style elite are here to help.

Take Caroline Shaw, for example, a.k.a. The Wedding Dresser. From initial consultation to point you in the right direction to on-site support during fittings and accessory selections, Shaw is Chicago’s go-to for styling and polishing happy couples. She can also handle those pop-up, day-of fashion emergencies (think steaming and pressing, pinning the veil just so, and last-minute tailoring and sewing should you need it). She’ll even stick around to position the entire bridal party for photos. “I come with my own steamer and a big bag of tricks,” says Shaw. “But most of all I bring you the peace of mind that whatever fashion hiccup might occur, I’ll be there to take care of it. The last thing you want to be worried about on your wedding day is what could go wrong.”

Seriously though, Shaw thinks of everything, including having straws on hand to keep couples hydrated without messing up their makeup. From the little things (say, boutonnière pinning) to hyper-specific asks (sourcing a custom kabuki handmade in Japan that needs to be folded around the body like origami), she has fielded all manner of requests. For her LGBTQ+ clients, Shaw likes to follow their lead—with some leading questions. “When I interview my couples, regardless of gender or gender preference, I always ask them how they want to present on their wedding day,” says Shaw. “I’ll ask, ‘What do you have in mind and what is it you are looking to wear? Do you want to be complimentary together with colors and fabrics? How do you dress as a couple socially? And how much do you want your looks to change for the wedding?’ Then I’ll create a mood board and go from there.”

“I find that most of my same-sex and trans couples are equally vocal about their style preferences, unlike hetero couples where the loudest voice is usually the bride,” continues Shaw. “It’s very 50/50—and I love that.” She also shares that it’s oftentimes important to her LGBTQ+ clients to represent and honor their community through their wedding day fashion choices. “It can be important to LGBTQ+ couples to embody their community via their image, especially on their wedding day—to do their community justice with an authentic, reverent statement.”

Longtime Chicago wedding planner Derrick Taylor, owner and creative director of Taylor & Co., works with Shaw often—personally and as a referral for his clients. “For some couples, weddings can be socially stressful,” says Taylor, who, along with his family, has been planning and producing dreamy weddings for more than a combined 75 years. “Your fashion can be your suit of armor. On the day of your wedding, you want to feel confident, and looking good will give you that confidence. It’s a feeling that transcends gender, and it’s human to want to feel fearless and self-assured on your wedding day. And trust me, I speak from experience here as a gay man… When I put on my Louis Vuitton shoes with the titanium heels, my confidence is impenetrable—and I can work a room like no other.”

According to Taylor, a lot of same-sex weddings are smaller gatherings. “In my experience, most gay men don’t want a big, sit-down dinner. They prefer a cocktail party with ample passed apps and mingling,” he says. “Which aligns well with the pandemic’s event size restrictions. When you pair down your guest list, you can do so much more with your budget—and that goes for your fashion choices, too. All of the sudden your budget opens up and you get to be like, ‘Yes, I am going to go to Dolce & Gabbana and get that hand-painted blazer—because I can, and because I’ll look and feel like a million bucks wearing it. Because I deserve it.’”

Shaw concurs, and is no stranger to controlling some of the shopping variables. “Hunting for and trying on different looks is part of the fun, and I don’t want some mindless assistant to say ‘Would your wife like a glass of Champagne?’ if that’s not how you identify,” says Shaw. “It’s all about the experience, and making sure it’s both joyous and respectful—and that you feel special.” Sometimes that can mean setting up fitting appointments for her clients and setting the tone for the staff. “We live in a world where we have gender fluidity,” adds Shaw. “People are coming around to gender neutral bathrooms, but I don’t think gender neutral changing rooms are quite there yet. Sometimes private fittings are best so there aren’t other people around whose reactions and comfort levels you can’t control.”

As for style direction, Michael Corrigan, the communications manager for Tie Bar, assures there are no rules. “When it comes to shopping for the big day, breaking traditions is the newest trend,” he says matter-of-factly. “You don’t have to wear white on your wedding day. And you don’t have to show up in a formal gown or tuxedo unless you want to. I have a friend who is getting married in Japan next year, and he’s planning on wearing hand-painted floral Gucci denim for his wedding with an ivory blazer and a decorative brooch—and it looks amazing. Five years ago I would have never given my stamp of approval for denim on your wedding day. But these days, I think rules can be bent and rules can be broken, and that’s when the most fun happens.”

Tie Bar is an excellent resource for “I do” menswear for those looking for quality and style at an approachable price point. The Chicago-based lifestyle brand recently rolled out a refreshed digital platform on the heels of bringing on Jim Moore, creative director for GQ, as an advisor for the company’s trajectory and image. “Tie Bar has always stood for style, quality and price. And while ties and accessories were the vehicle for that initially, in recent years we’ve been thoughtfully adding clothing categories—dress shirting, casual shirting, dress pants and dress chinos, followed by sweaters and polos, and a retooled sock program,” says Corrigan. “Today, Tie Bar is a true style authority. We’ve become a brand that can help you effortlessly tie it all together.”

In terms of raising the style bar on masculine looks for the big day, Corrigan recommends Tie Bar’s new non-iron linen shirts for summer receptions. “Classic linen has a shelf life. There’s such a fine line between beach-chic and a rumpled mess. Our non-iron linen is a game changer—and will hold its shape throughout the day. Pair with Tie Bar’s stretch-cotton dress chinos and, say, a silk linen blazer from SuitSupply, layer in some colorful accessories from our Liberty London capsule collection and boom… You’ve got yourself a no-muss, no-fuss big day look that’s sure to impress. For a long time, wedding style was such an afterthought for men—gay and straight. But now it’s cool for both partners to show off their personal style for themselves and for their partner. And to be the best representation of themselves.”

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