For many grooms, picking out the big day attire is a daunting task, particularly if your usual date night outfits incur a little side eye from the now bride-to-be. Plus you have the unenviable task of herding all of your groomsmen for a fitting. Our advice? Don’t fight it, make a day out of it. Call it Bachelor Party Lite. With all of the other wedding-related tasks you have to tackle, this one has the highest ceiling for added fun. Think of it as another chance to hang out with your favorite crew, so make the most of it while you have an excuse to get the gang together. To make it easy as possible, we put together this your itinerary just for you and your groomsmen…
12 p.m. Chow DownButtermilk & Bourbon 160 Commonwealth Avenue, Boston, MA 02116, USA
Kick your mission off on the right foot (with a full stomach) to eliminate any threat of hangry group members. And what better place to get in the classy, gentlemanly-state-of-mind than lunching it up at Back Bay’s Buttermilk & Bourbon? With southern inspired food options, and a Bloody Mary bar that will tempt you to post a shot to Instagram (fight that urge), everyone in your crew will be satisfied and fueled up to power through the day.
2 p.m. Look SharpBarbershop Deluxe 288 Columbus Ave, Boston, MA 02116, USA
After a few rounds of waffles and old fashioneds, head over to Barbershop Deluxe and get your groomsmen looking fresh. They are going to have to look in the mirror for the next couple hours, after all. Whether you’ve been meaning to get a trim, or just enjoy a straight-razor shave, there’s no better place to bond with your boys than a barber shop. Think of this as preseason game for the actual wedding. Getting ready together now will make the experience on the big day feel more familiar and hopefully cut down some of those jitters.
4 p.m. Get FittedIndochino 85 Newbury St, Boston, MA 02116, USA
Now that you’re all feeling the “clean shaves/full stomachs/can’t lose vibes,” it’s time to go pick those ‘fits. Walk a few blocks over to INDOCHINO for a very proper suit fitting. Start out by talking to your Style Guide about where you’re getting married, what time of year, and any “vision board” buzzword your fiancé has thrown around over the past few months—trust us, this will pay off big in the long run. The Style Guide will take over and explain fabrics, measurements, and customizations, so you and your team can start trying on and picking those suits.
Up the ante by making the suit choice a March Madness style contest, having a couple groomsmen walk out and model their selections in a face off. Once you’ve made your selections, get a few pics—they’ll be fun to look back on, and score some points with your bride.
6 p.m. Perk UpThinking Cup 85 Newbury Street, Boston, MA, USA
Shopping can actually take a lot out of you, so pop over to Thinking Cup down the block for the best coffee in beantown (don’t @ me) as well as a full case of pastries and confections that might start some salivating in line before you order. But don’t let that sugary display distract you—the real gem is the grilled cheese menu. We’re talking any bread, any cheese. Just make sure you grab plenty of napkins.
8 p.m. Close The TownDillon's 941-955 Boylston Street, Boston, MA 02115, USA
You did it—the suits are chosen and that box is checked. Time to celebrate! Let loose at one of Boston’s sports spots on Boylston: Dillon’s has a wall of TVs so you can catch the highlights of the games you missed while shopping, and a great patio if you’re doing this during one of the three months that don’t require four layers of clothing in this city. Grooms, make sure to raise a glass and thank your support system for joining the day and keeping it fun. Now let’s see who’s left standing at last call.