Bentley Caldwell

JUNE 2023 “A Look That Suits You”

Each month Nashville #1 Men’s Personal Stylist, Bentley Caldwell will weigh in on the latest trends and answer men’s styling questions. His partner in crime, Carson Love will share her style tips for women.


His Style: Let’s talk tailors 

Gents! Celebration season — graduations, weddings, mitzvahs and more — is now upon us, so let’s talk about suiting up. Specifically, tailored suits. I always tell my clients: “If you can afford a tailored suit, do it!” 

Why? First, unlike off-the-rack suits, a tailored suit is tailored to fit the unique measurements and proportions of your body. Second, a tailored suit allows for greater personalization and customization. If you’re partial to a periwinkle blue suit with a print of Van Gogh’s The Starry Night as your liner, go for it! I mean, good luck walking down the street, but go for it!

With tailored suits, you have the power to choose the fabric, the lining — even the buttons — ensuring that you create a one-of-a-kind suit. Third, a well-made tailored suit — plus proper care and maintenance — can last for years, making it a smart investment for both style and practicality. Who doesn’t love a good ROI; am I right, fellas?

Here are things to consider when purchasing your first tailored suit:

Tailor to Your Preference

Suiting is typically divided into four categories: Off the Rack, Made to Measure, Custom and Bespoke. OfftheRack refers to any suit you buy in a clothing store at the mall — what you see is what you get. MadetoMeasure refers to altering an existing pattern or design to fit your measurements, but the suit is not completely unique to you.

Custom, on the other hand, involves taking your measurements and creating a pattern specifically for you. (Confused yet?) Bespoke tailoring is the highest level of customization in suiting. It involves creating a 100% unique pattern for you based on your measurements. The suit is then made from scratch by the tailor. From scratch. Like a batch of your grandmama’s biscuits. 

Do Your Research

Getting a tailored suit is a collaborative process between you and your tailor. Make sure you choose the correct tailor that matches your vision. Nashville has a strong men’s tailoring community (Levy’s, Eric Adler and Richards Bespoke, just to name a few).

Check out their websites. Check out their social media. View some of their previous work to find the right guy or gal for you. It’s almost like dating, minus the awkward conversations over sushi and sake.

Be Prepared

Come in with an idea of what you want. Some tailors may ask you to bring in your best-fitting suit or blazer for reference. Some may ask you to bring reference photos to aid in the vision. The worst thing you can do is walk into your suiting appointment with no idea of what you want. It’ll turn into the “What do you want?” scene from The Notebook with Ryan Gosling and Rachel McAdams. (Spoiler alert: You won’t be Gosling in that scenario.)

Overall, if you decide to go down the tailored suit road, enjoy the process! It is a beautiful experience to see your name stitched on the inside of a one-of-a-kind suit jacket.