The rules of fashion, like many other things, have been rewritten and your go-to style tricks from the turn of the millennium may not hold up today. If you’re feeling unsure about how you're supposed to look, this is the guide for you.
1) Let’s take stock of what you have and build on that.
Most guys will have a comfy sneaker that’s meant more for off-road than city, trendy sneakers that may or may not be adidas Stan Smiths, Nike Roshe Runs, or adidas Yeezy Boosts, natty Vans slip-ons, and chunky square-toe black leather shoes from nineteen-forgotten a.k.a. from way back when the school dictated how you dressed. The first thing that could use some updating is your footwear selection. Cop a pair of sleek leather loafers. Think Belgians, driving shoes, or for the more label-loving, Gucci horsebit loafers. Dr. Martens also has options that are at once trendy and timeless. BTW, the city is not the place for your Merrells.
2) Dress for the occasion.
No matter how many times the fashion set will contest occasion dressing, nothing simplifies picking an outfit better than knowing where you’re headed. The easy question is, should you dress up or dress down? The rule of thumb is darker jeans for more dressy occasions; whatever goes for casual. Likewise, stuffier events require leather shoes. For an easy guide on proper footwear, check this.
3) Pick the pants.
For pants, tapered, slim, or straight are all fine picks. Boot cut is out of the question. Wide-leg pants are acceptable if you’re feeling bold. Patches and rips, however trendy, should be reserved for casual occasions to be safe.
4) Mix and match.
Time for the actual pairing! Casual shoes and ripped jeans is a combo that has been perfected since the birth of Converse. You can’t go wrong there. The trickier part is wearing dark wash jeans with leather shoes. Neutral colors are always safe and go well with each other. Black shoes, despite their severe reputation, can easily be balanced by modern shapes. Brown, however, doesn’t play well with black, so avoid wearing both together.
5) Finding the right pair.
While there are no hard and fast rules, these tips might help you find the right pair. Joggers go with any kicks, but may look odd when paired with a proper derby. Tapered and slim pants can work with most anything, while wide-leg pants only go with chunky shoes. The key is knowing when you need to reign in the shape of the pant-leg and cuff it. But it’s best to leave wide-leg pants as they are (or cuff them without tapering it) as they give you an unwanted genie effect. You don’t want to look like you’re wearing bloomers!
6) A few tricks up your hem.
A simple turn-up can turn your look from ordinary to stylish. A simple inch-thick cuff can nicely show off the hem of your jeans and let the world know you’re wearing selvedge. The pinroll is also another favorite way to flaunt your kicks and trim the silhouette of your pants. For more proper occasions, steer clear of cuffing. If needed, a more discreet fold is prudent.