by Silk Allen
Dear Lady Silk,
(Plain Press, November 2018) I’m a thirty-nine-year old man that likes to go out with my girlfriend and I have a hard time understanding what clothing styles work best for me. I’m not trying to dress super flashy like the young guys I see with the loud tight shirts and jeans, but I am also not ready to wear my pants up to my chest with high socks and suspenders either. How do I achieve the proper balance of not dressing too young or too old for my age?
Modern but not like Migos
I’m glad that you have not succumbed to the pressure of dressing like an out of touch rapper, or like your old uncle Bob, as so many men your age tend to do. Your twenties were the perfect time to experiment with fashion, but your thirties and beyond are all about fit and style. You should rely less on trends and more on the quality, design, color, fit and fabric when it comes to building your wardrobe.
When you go out with your girl, you want a look that reads as confident and classic so stick to clothes that offer a sleek and dark silhouette like a black pima cotton t-shirt and jacket with a pair of dark jeans and leather sneakers for a night out at the bar or a lightly patterned dress shirt, gray blazer and charcoal trousers for a dinner date. Your clothes should frame and skim your body not hug or drown you, so make sure you take three sizes (the current size you wear and a size up and down from that) with you to the fitting room until you know what looks best on your body type. Use the following list as a shopping guide for a very well edited wardrobe and you will easily be one of the best dressed men in any room you enter.
• White Dress Shirt: This top is versatile enough to wear under a suit for work, underneath a sweater with jeans for the weekend and tucked into a pair of chinos with a nice belt and shoes for a dressy casual look. Look for a thicker cotton and buy several if you can.
• Collared Shirt: Long and short sleeve button downs in solids or prints will help extend your wardrobe for work and after hours. They look good underneath a sports coat worn with chinos and casual shoes and work well with a pair of dark blue jeans and tennis shoes too. It’s also a perfect layering piece for fall if you add a sweater or cardigan on top.
• Casual Tops: Leave the tie dye, logo heavy, message tees for the gym and invest in a few polo style shirts, Henley tops and cotton tees in a variety of colors. They can be worn with any style of pants and easily add color to your wardrobe. Black, white, gray and earth tones usually look good on everybody, but don’t be afraid to experiment with deep colors like shades of red, blue, plum and charcoal.
• Trousers: Step your pants game up with a pair of black or navy chinos and khakis and see how much wear you will get out of them! Wear them with a shirt and sports coat or a Henley and bomber jacket. These pants are the perfect alternative to jeans.
• Wool Dress Pants: You can wear these pants with a patterned button down or with a sweater and blazer on top for any upcoming holiday parties you may attend. They are a great balance between casual and formal.
• Jeans and Joggers: I’m not telling you to get rid of your oversize, faded and holey jeans and stretched out, bleach stained ratty sweatpants- yes I am. You deserve better. Purchase a pair of quality jeans in a dark wash and slim (to your body) fit. Black jeans are also good to have on deck as well. It’s OK to wear sweatpants sometimes (hey men have “fat” days too!) just don’t rely on them and make sure they have some sort of shape. Layer a crew neck sweater over one of your tees and add your tennis shoes.
• Sweaters, Jackets and Blazers: Ditch the hoodie or just wear them to the gym and around the house. When you step out, a crew neck sweater, cardigan, blazer or bomber style jacket will keep you just as warm, are one hundred percent more stylish and looks more mature when worn with jeans.
• Sneakers: Leave the wild bright colors and bulky shapes to the younger guys and try a classic pair like the Adidas Stan Smith sneakers or any other streamlined style that would look great with your polo top and trousers or patterned short sleeve dress shirt and jeans.
• Dress and Casual Shoes: Black and/or brown oxfords will work with your suits and any other dressier attire. Casual leather and loafer style shoes look great with chinos and trousers and choose from a chukka, desert or Chelsea style boot when you want to be comfortable but still give a nice fall look.
• Suit: You should have a few suits by now, if not start with your basic colors- navy, black and gray and then expand by weights, texture and patterns like tweeds and plaids. Don’t be afraid to mix and match by breaking your suits up and wearing the jackets with other pants and the pants with a nice shirt and tie combo.
• Extras: Purchase a black and a brown belt, go wild with socks, pocket squares, ties, and bowties as far as color and pattern, but be sure to get your standard solid colors as well. Make sure that you have an overcoat of some sort that will fit over your suit and blazer. Parkas and peacoats work for casual wear and can be layered for when the temperature drops. Invest in a good overnight bag and wallet for travel and keeping your cards and money safe. Buy an umbrella on purpose so you don’t get soaked or have to pick up whatever is available at the drugstore. Splurge on skincare, eyewear, a tailor and a signature cologne, because they are the seemingly small things that will pull your entire look together and make you stylish at any age.
As always, I’m here with answers to any of your style questions, so don’t hesitate to email me firstname.lastname@example.org and put “Ask A Stylist” in the subject line!