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Style Advice From Drew Kenney!

SO excited for my second Men’s Fashion feature on the blog!! This month I was lucky enough to meet up with and interview a fellow-bachelor contestant who also shares a passion for fashion (but maybe not for my bad habit of rhyming). You’ll probably recognize Drew as the incredibly gentlemanly runner-up on Desiree’s season of The Bachelorette!! Since the season ended, he’s been super busy with his move from Scottsdale to L.A. and along with modeling and acting, he’s started a fashion-based social media/marketplace for people to show off their style AND buy/sell/trade pieces from their closets all while donating to charities of their choice. Busy man and kind of a mouthful. Drew, you’re putting us all to shame a little!!!


My Interview with Drew:

Jilly: What do you feel most comfortable wearing?

Drew: I’m most comfortable in workout clothes, and wear them as often as I can. When that’s not quite up to standard, it’s hard to beat a good fitting pair of jeans!

Jilly: How would you describe your style?

Drew: I like simple and classic. I think the details and how you piece everything together are the most important features when creating a wardrobe. If there was a fashion icon that I were to try to replicate, it would have to be James Dean.

Jilly: Do you think your style has changed now that you have moved from Scottsdale to Santa Monica?

Drew: Maybe slightly, but I think my style has remained constant my whole life. I still wear the same kinds of clothing that I did when I was in high school. Now if that means my style is outdated, or it is classic enough to transcend periods of my life, I don’t know, but it’s what has always felt right to me.

Jilly: What’s your favorite men’s fashion store?

Drew: Recently, I’ve been really into small business clothing lines. Élevée and Unsimply Stitched have become a couple of my favorites. Élevée will tailor everything to fit your exact measurements. It’s impossible not to feel like you are looking your best when wearing their clothing.

Jilly: How many suitcases did you pack to go on The Bachelorette (I’m guessing not as many as me!!)?

Drew: I packed A LOT! Well, for a guy I suppose. They tell you to prepare for winter and summer type climates, so you’re forced to bring thick winter coats AND tank tops. I ended up packing two very full suitcases and two garment bags, but came home with even more because you pick up things along the way.

Jilly: What’re your thoughts on bowties?

Drew: I think bowties are a great look! I love it when they are pulled off well. I’ve worn many bow-ties, and as a matter of fact, I’m on my way to a friend’s wedding where all the groomsmen are wearing wooden bow-ties, so I’m excited to see how that turns out.

Jilly: I have to know…who’s the best dressed Bond? Sean Connery, Pierce Brosnan or Daniel Craig?

Drew: Now you’re speaking my language! Bond has always been a cornerstone for elegant yet masculine fashion. Credit goes to Connery for being an original, but Daniel Craig is a favorite of mine. I’d have to say its a tie between them.

Jilly: What’s a must-own men’s accessory?

Drew: Believe it or not, I’m going with socks with creativity. Accessories can get very expensive real quick, but socks with personality always get noticed

Jilly: Did you look forward to “suiting-up” every Rose Ceremony on the Bachelorette?

Drew: I did! I always feel my best and most confident when I’m dressed well, and when it came to Rose Ceremonies, I needed all the confidence I could get! Not only that, but I felt like making sure my suits were on point was one more way for me to get noticed and set myself apart when it came time to hand out the fateful flowers.

Jilly: What do you typically wear on a Sunday morning?

Drew: I like to walk to Mass on Sunday mornings, so it’s church attire that day. I usually wear a nice pair of shoes, some khakis, and a button-down shirt; short-sleeve in the summer or with a sweater in the winter.

Jilly: Converse or loafers?

Drew: I have had so many pairs of Converse over the years, so I would definitely have to side with the Chuck Taylor’s.

Jilly: I’m sure the ladies are curious…what do you find the most attractive fashion style on a girl?

Drew: I’m from the Arizona, so I’ve always had a soft spot for sun dresses and sandals. Women are naturally sexy. They will be attractive as long as they are confident.

Jilly: If you were to come visit us in Canada, what’s the first item you’d pack?

Drew: I’ve always wanted to visit Canada! There is so much beauty there that I want to experience. If I were traveling there, I would have to bring warm clothing because it gets a lot colder there than what I’m used to in the southwest. I think I would have to pack some denim jackets and flannel shirts as well.


BIG THANKS to Drew for sharing some styling tips, Bachelorette insight and for being some serious eye-candy on Desiree’s season! Hehehe. Loving his bespoke & monogrammed shirt!!

Definitely check out the landing page for Drew’s new site at and sign up to get updates. It will be up and running so soon and I can’t wait to check it out!

xoxo Jilly

ps – Stay tuned for the next Men’s Fashion Feature…it’s going to be a good one!!

First look:

Ray Ban Wayfarer via Mr. Porter | Sweater Via H&M(similar) | Shirt via H&M (similar) | Levi’s Jeans via Macy’s

Second look:

Bespoke Shirt and Jacket both via Élevée Lifestyle |Pants via H&M (similar) | Johnston & Murphey Shoes via Lord & Taylor (similar)

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