How to Dress Up That Pair of Jeans


I spent the past weekend pulling my jeans out of storage for the first time in months, and I'm trying to plan some eye-catching fall outfits to wear when I go out. Jeans are a great fall/winter alternative for the lightweight slacks and khakis you've been wearing all summer for parties and outings. Jeans are warmer and more durable than slacks, plus they won't show the stain when you spill half your cider on your pants (it can happen to anyone guys). With fall fashion in mind, here's our quick guide to dressing up your jeans.

I recommend going with dark denim for nicer outfits. Dark denim looks sleeker and less, well, denim-y--a bit more sophisticated, a lot less cowboy. Wide-leg pants are making a comeback this season, but I would choose something that flares at the bottom, like a boot-cut, while still hugging your legs and waist a bit up top. Baggy pants tend too look informal, and, in my opinion, a bit juvenile. Show off those legs instead.

First up is your shirt. A good dress shirt instantly makes any jeans outfit seem more formal. A quick word of caution, though: you don't want to choose a shirt that's too formal, otherwise it will clash with the jeans. (Also, you don't want to risk damage to your nicest shirts by wearing them all about town.) So, hang that extra-fancy Italian-made shirt back up and save it for a suit. A nice Oxford button-down, like this striped shirt from Lands' End or this grey twill shirt from J. Crew, would hit that perfect mid-point between dressy and casual. While solid colors do fine with denim, pairing patterned shirts with jeans can create a more eye-catching look. This checked purple shirt and dotted navy shirt, both from Bonobos, are bright and fun without being too bold.

I'm only a recent convert to the blazer-and-jeans look on guys, but it's starting to grow on me. A nice navy blazer never goes out of style and can create a cool faux-suit appearance, but a gray blazer creates a nice color contrast and is in line with this year's fall fashion. However, this is also the sort of outfit that's great for breaking out a nice sweater to wear over your dress shirt (see our guide for that here).

Remember that accessories make an outfit--that adage is especially true when it comes to sprucing up a pair of jeans. You definitely want to pick a good belt to wear with the outfit; it makes the jeans look nicer and draws eyes to your shirt. I'm a fan of this brown brass belt from Todd Snyder (somebody I know is getting it for Christmas). I think that it's fine to wear a tie with a jeans outfit, but remember our rule that you don't want something that looks too formal. Rather than compliment your jeans, a silk tie will stand out too much and just look wrong with the outfit. Instead, try a wool necktie, like these blue and gold herringbone ties from Bonobos; both invoke a real sense of autumn. For a bolder choice, this cable-knit tie from Lands' End is unique and looks like a more formal version of a scarf.

The main goal with any dressy jeans outfit is to make the jeans look more formal and exciting than they actually are. The result is an outfit that looks nice for going out but is comfortable to wear; it feels a bit like cheating the fashion system in a fun way. Start mixing and matching with your favorite dress shirts and accessories to create a look that's right for you. Feel free to share some of your new fall outfits with us on Facebook!