It’s a struggle I see far too often: a girlfriend attempting to dress her T-shirt and athletic shorts-loving boyfriend; invariably this battle of wills results in a rather unpleasant spat with neither side conceding much ground. As a guy who loves clothes, I have some ideas to help find a middle ground with outfits you both love.
1) Chukka Boots- These are without a doubt my favorite shoe. If your man is concerned about maintaining his manly appearance, fear not! This shoe is both classy and rugged and looks FANTASTIC with jeans and flannel button down. You will pay a price for such a compromise though, J.Crew’s version of the chukka, the MaCalister(it even sounds manly) comes in at $135 for the suede version and $148 for the oiled version. Naturally, I prefer the more expensive.
Why he’ll like it: It’s a relatively lightweight shoe that’s more comfortable than other dress shoes because of the flexible materials.
2) Corduroy Sports Coat- These jackets are perfect for fall and early winter because of their light weight. They look great and can really tie an outfit together. Granted, they are a bit dressy; but, many guys like them for their unique look. I prefer a dark brown or chocolate color but they also come in grey and tan. The great thing about these is they can essentially pair well with any color except black. I am definitely a fan of Calvin Klein’s taupe and Ralph Lauren’s brown.
Why he’ll like it: It’s unique and mildly eccentric. Plus, everyone thinks they look great. I get more compliments on mine than any other article of clothing.
3) Flannel- Flannel is a definite crowd pleaser. It’s warm and comfortable and if worn correctly can look very nice. To make flannel work, make sure the colors are fairly versatile. Reds and blues are a safe bet because he can always pair with dark washed jeans and be good to go. For an extra special event, he can tuck it in and wear a brown belt and look very classy while still maintaining a more casual feel. J. Crew has some excellent options in red and blue.
Why he’ll like it: It’s soft, warm, and easy to match. Plus, it does not carry the risk of being labeled “preppy” or “metrosexual.”
4) Cashmere Sweaters- Crewcut or V-neck, you simply can’t go wrong with these. Cashmere, though pricey, is luxuriously soft and tremendously warm. Pair this with either a plain cotton t-shirt or a neutral button down and you’re in business. The great thing about these is how easy it is to make a coherent outfit. Any color sweater will look great with a white under shirt or a neutral button down, like grey. If you have to settle for one, though, definitely go with black because of its versatility. Pair with any type of pant and he’s good to go. Cashmere is pricey though so look for cotton-cashmere blends or wool-cashmere blends.
Why he’ll like it: Easy to match, soft, and warm. Need I say more?
5) Dark washed jeans- Dark washed jeans are the close cousin of the regular blue jean; it simply has a darker color. He won’t be able to tell the difference, but you’ll see a much cleaner, classier version of his favorite winter pants. Also, because the dark color makes it relatively more neutral, it’s easier to match. Don’t get caught up in all the fancy cuts. Stick to a bootcut, regular, or loose fit and you will hear no complaints from him. Levi’s are always a safe bet.
Why he’ll like it: It’s essentially the same as the jeans he’s been wearing for years.