How to Dress Your Man This Holiday Season

11 years ago when I met my husband, he was a t-shirt and jeans type of guy. Not just any t-shirt, but sports t-shirts and basketball shoes off the courts. I was a fashion design student with a wild and edgy personal style and well, our looks didn’t exactly really mesh well.

When I was picking out clothes for my husband, I discovered my love of styling and personal shopping. Fast forward to the present day and my husband is one of the most stylish men I know. I no longer dress him. Well, rarely. He knows what he likes, what styles and brands fit, and he can practically teach other men the art of personal style at this point. (In fact, his friend’s have jokingly named him “Mr. GQ.”) I’m so proud, but it took work to get him there.

My advice for all you ladies? Don’t try and change your men but this holiday season, give them a nudge in the right direction towards finding their own personal style.

Here are a few of my tips, with a few from my industry friends, as well as “Mr. GQ” himself, about how to dress your man this holiday season.

  • How To Dress Your Man 1 of 11
    holiday pic

    This was our family's holiday wardrobe last year. My husband considers this look "somewhat casual." His style tips are included below!

  • Gabriel Charles’ Tips 2 of 11

    Gabriel Charles Tyler is a journalism major as well as a published writer, fashion blogger, consultant and Chicago native. His personal look makes him an instant authority on style and a staple in the Chicago fashion scene. 

    Image provided by Gabriel Charles Tyler

  • Dark-Hued Denim 3 of 11
    photo 2

    "Dark-Hued Denim is a Wardrobe Staple that works during the Holidays and beyond. Ladies, it's not what he wears, it's how he wears it. I live by the rule that denim, especially darker hues, can always be spruced up to fit any occasion. In fact, I haven't worn a pair of dress pants to a holiday event in years. Whether it be a casual, family dinner or a dressy gathering, a good pair of denim jeans will allow your man to be comfortable, but still on trend."


    Model: ReShai Tate
    Customer Experience Lead at the Banana Republic Women's Specialty Shop (900 N Shops)

  • Blazers Are Always A Good Touch 4 of 11
    photo 3

    "Blazers are not a Must, but they're definitely a good touch. Donning a blazer symbolizes that a man has matured and made the transition into manhood. It shows that he's traded the typical khaki and button-down look for something a little more sophisticated. And the best thing about them is that they're additions to any outfit that can always be removed. If he's the only one wearing one, have him ditch it."


    Model: ReShai Tate
    Customer Experience Lead at the Banana Republic Women's Specialty Shop (900 N Shops)

  • Go For Grey 5 of 11
    photo 1

    "Gray is the most underused, but necessary color of the season. I've heard that black and white can match with any other color, but for me the most transitional color is gray. Whether you're spending the holidays somewhere cold or somewhere relatively warm, the right tone of gray is appropriate for any type of weather. It's also a fail-sure way to be dressed appropriately dressed for any event. A gray two-piece suit can be worn to religious ceremonies, office parties and mostly any other holiday event."


    Model: ReShai Tate
    Customer Experience Lead at the Banana Republic Women's Specialty Shop (900 N Shops)

  • Ryan’s Tips 6 of 11

    "Dressing for the holidays doesn't have to be a chore - and you don't always need to take yourself so seriously when doing so. My two tips for dressing for the holidays mirror that very idea: how to take a serious outfit and add an element of fun and personality."

    Ryan M. Beshel is the Digital Marketing lead for Purely Fashion. He has worked in PR for the 900N Shops, was the Director of Runway at Agency Galetea (and one of my agents as a signed stylist) amongst other things. He is well known, well respected and sought after amongst Chicago's fashion's elite. 


    Image by Hallie Duesenberg  


  • A Fun Classic 7 of 11

    "Bring back a classic. My go-to shoe may surprise many people - but, the Chuck taylor is the ultimate every-outfit-shoe for me. Add personality and fun to the standrad dressy look to bring a more casual feel to the holidays. A bold red Chuck Taylor with a pair of black denim, a woven shirt and a suit coat makes for a look that says "I'm serious about looking good - but, I don't take myself too seriously." Make sure the Chuck's are clean and new - and stick with a solid color that compliments your outfit."

    Image by Rumala Sheikhani 

  • Extraordinary Accessories 8 of 11

    "Bring back the bowtie. Over the years, I have been known to rock the bowtie every chance I get. Take your standard necktie to new levels by switching it out with a bowtie. This mens accessory has recently made its way back into style and a bowtie makes you an automatic stand-out, trust me. The bowtie screams fun - and can take your outfit from ordinary to exrraordinary. My one rule when wearing a bowtie is to be sure to learn how to tie one yourself. An avid bowtie wearer, like myself, can pick out an pre-tied bowtie from a mile away. Don't get caught looking like a novice - try a YouTube/Vimeo tutorial (Here's one of my faves!) to learn how to tie one for yourself. Once you learn, it's like riding a bike you learn once and you'll never forget it."

    Image by Emma Arnold

  • Mr. Garza’a Tips 9 of 11

    This is Eduardo. My husband of 11 years, who dresses himself so effortlessly that sometimes it bothers me that he doesn't need my help. I'm over the moon when he does ask me, "How do I look?" Even if it's just to make me feel better. While his day job is in finance, by night he is a cologne expert and has a serious obsession with Tom Ford. 

  • Mix Prints 10 of 11

    "I used to prefer a simple look, but no one remembers a man in a simple look. Now I prefer to mix styles and prints. The key to mixing prints is to keep the color story relevant. As long as the prints and patterns aren't wild and the colors are relatable or monotone, mixing prints is easy."

  • In The Details 11 of 11

    "Focus on the little details. A suit looks great, but a well pressed suit with cuff links and a pocket square can elevate the look. I wear one everyday for work so during the holidays, just changing something as simple as a pocket square or a tie into something more festive is a great route to take." 

Article Posted 3 years Ago
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