For folks not interested in style, clothes can be frustrating. “What? My pants are too tight? Ok, I'll buy baggy ones.” 10 years later… “What? My pants are too baggy? But…but…”
There are a lot of style fundamentals that stay relatively consistent over time, and that's the kind of thing we try to discuss in length on Primer. There are, however, trends that come and go, and then come again, then go down in a whirlwind of hate, and then pop back up in 30 years as being cool. (Skinny ties, I'm looking at you.)
Why, just a few years ago I remember having a hard time finding the “in” trend in jeans at an affordable price: bootleg. Now, up until a season or two ago, it was impossible to find anything other than a bootleg in a flattering non-Dad fit.
Yes, trends come and go, and it can be horribly, horribly annoying. I've often been frustrated and thought, “who makes these decisions?” The fashion elite, most likely, which it then trickles down from the runway, to eventually Gap and J.Crew. Sometimes I welcome them, I love the sleek, mod inspired suiting options that became trendy a few years ago. I find the slimmer cuts and thinner lapels to complement modern styling in shirts, ties and atmosphere.
Sometimes it's infuriating – as I feel now with double-breasted suits that are being pushed down our throats all over runways and style magazines. I may be putting my foot in my mouth later, but I can't imagine me, or any other everyday gent sporting a double-breasted jacket in a normal, non-high fashion environment. It's just too formal for anyone other than folks with street-style blogs.
That's why I don't want you to read the following list of out of style clothing trend sand think, “Oh yeah? Says one idiot on one stupid website.” I get it–not wearing a shirt that is in good condition, or a pair of shoes that still have years of wear left in them just because it's “not popular” is a pretty shitty reason. I get bogged down in existential thoughts on the function clothing performs and wonder if we're all just suckers buying into advertising. Nonetheless, the following items are out of style, and if you're concerned with such things, you should consider phasing them out of your wardrobe for more timeless alternatives.
1. Square-toe Shoes
If you're only going to ditch one out of style clothing trend, make it this. Nothing screams late 90's more than chunky-soled, squared-toe dress shoes. A combination of a boot and a dress shoe, these shoes are prevalent among guys who are still wearing the first pair of dress shoes they bought in college. Kenneth Cole made a bajillion dollars off of all of us, but it's time we retire these bad boys.
When the time comes that you can replace 'em, opt for a shoe shaped more like a typical oxford like these wingtips by Johnston & Murphy. Even if other styles pop up along the way, this shape of shoe has been a standard for generations.
2. Jeans That You've Been Walking On
I remember in college several years ago, it was pretty stylish to have the back side of your jean leg be all ripped up because they were long and baggy enough that you would walk on them. Since then, we've come to our senses a bit, and the uniformly accepted style is one that is slim and fits more like a pair of suit pants than skater jeans.
This problem is actually caused two ways. One, your pants are too long. Or two, the profile of your shoes is slim enough that the jeans slide right over them. For example, if you're into stacking your jeans, you're probably wearing thicker shoes that hold the jean legs up, preventing you from walking on them. But if you're donning slim white canvas sneakers or boat shoes, you need your jeans to be shorter.
As you phase out your shredded jeans, look for a straighter fit, with legs that end at an appropriate length based on a majority of the shoes you wear. This is one of those mistakes that cause people to think you're younger or more immature than you are.
3. Really Wide Clown Ties
I'm expecting to get roasted on this one, but I'm going to stand my ground. For most guys, with most body types, your tie should be 3 inches wide or less at its widest point. And even then, that's pretty freakin wide.
Conventional business attire for the last, I don't know, 40 years, has included wide, 3″ to 3.5″ ties. That's so big! I'm an average build 170 lb guy, and if I wore a 3.5″ tie, it would be 25% to 30% of my midsection. Way out of proportion.
Most of my ties are right around 2.5″. It's a nice balance for my body type, and appears in proportion with the rest of what I'm wearing. That should be your go-to in my opinion. Now, if you're a bigger guy, you can go for a bigger tie, absolutely. Remember, tie width should be proportional to your suit jacket's lapel width. So unless you're wearing some wicked John Travolta collars, 3.5 inches is just gigantic.
The skinnier your tie, the less formal it becomes, so if you're trying to rock the casual tie, pick one that's on the slim side. I have a wool 2″ tie that I love to wear casually.
4. The Velcro Wallet
Hey man, I get it: It's functional. I had a Quicksilver velcro wallet for years, and I loved the hell out of it. There was a time when the sound of undoing a diaper at the cash register was acceptable. The present is not included. Find a sale on a conservative leather tri-fold or a flat card case wallet like the one I have from Tagsmith. Saddleback Leather also makes some nice wallets, and they're pretty affordable.
Outside a watch or tie, men have very few accessories to class up and show their personality. A wallet is a nice, functional item you can get years of wear of. When the table pulls out their wallets to split the bill, make sure you're pulling out your best.
5. Wrap Around Sunglasses
The year: 1998. I was on a field trip to Washington, DC and I couldn't have cared less about the monuments or the White House. I was on a mission–a mission to obtain a pair of knockoff Oakley sunglasses from a street vendor. They were all the rage, and I was just a kid, who would never be able to afford the full price at the mall.
The key words in that paragraph are “1998” and “kid.” Some sunglasses are timeless, or come and go frequently, like the aviator, Wayfarer, or Clubmaster. Sometimes skinny frames are trendy, sometimes big fat goggles are the trend. The one trend that has not returned since it left (awhile ago) is the wraparound style made popular by Oakley in the 90's.
I'm sure I'll hear some excuse about them being functional for sports, or snowboarding, or what have you. Hey man, that's cool, you do your thing. But if you're out for a nice Saturday with your girlfriend try swapping them with a square-framed aviator or Wayfarer. They're classic and they look good whether you've got a pencil head or big ol' blob face.
6. Steve Madden Style Shoes
Like square-toe shoes, these half sneaks, half casual dress shoes, became de rigueur of the 20-something guy stuck in that period where he couldn't dress up too much because his friends would make fun of him. Well, even if you're still in that position, there are some alternatives that are a little more stylish but equally casual.
Try a Desert Boot. The look of a low profile put-together chukka boot, with the comfort of a sneaker. The Desert Boot has been a sartorial staple for decades, and if you opt for a pair in a darker color, they may well last you for decades to come.
You can wear them with anything from jeans, chinos, or corduroys. And if you follow The Getups you'll recognize how versatile they are.
7. Billowy Dress Shirts
It used to be hard getting a trim fit dressed shirt for less than the cost of a Playstation. Luckily more budget friendly stores like H&M have expanded into a lot of areas, and traditional go-to's like Gap and mall department stores now offer slimmer fits for reasonable prices.
The problem with mass-produced clothing lines is sizing has to be universal enough to fit a wide range of body types. So, a few years ago when stores only offered one cut it had to fit big and small alike. Now that we have options it's time to take advantage of them. Nothing looks worse than a muffin top and blousy pirate sleeves.
The new cuts go by many names, slim cut, tailored fit, modern fit, and athletic fit.
8. Velcro Sandals
Sandals, no matter what style they are, can be hard to pull off. Flip flops are common, but they're very “Hollister” and should be kept to places near water.
Velcro sandals like Teva should only be worn by two types of people: free-toeing hiker types and Berkeley professors. And of course, no socks with any sandals ever, ever, ever.
9. Wide Leg / Bootcut / Flared Jeans
Pants have been getting trimmer and trimmer since the 90's. Remember when everyone wore baggy jeans and sagged them? Then wide leg jeans became popular, which are essentially more tailored baggy pants that are slimmer through the thighs. Then straight leg became standard, and now they're pushing tapered skinny jeans on us.
I'd stick with straight leg jeans. They'll accommodate the most amount looks, fit great with a pair of bluchers or Red Wings alike and you won't have to do the girlfriend shimmy when trying to pull them on. My current favorites are a pair I picked up from H&M for $20 (not even on sale) and a pair of Levis Shrink to Fit 501's.
Bootcut jeans are still widely available at retailers but don't let that fool you: it's definitely past their time.
10. Baggy Cargo Shorts
I can still remember being excited about wearing cargo shorts in the 90's. Before them, the only thing that existed for young guys were carpenter jean shorts, and there's a reason those aren't around anymore. Baggy cargo shorts, made infamous by the likes of American Eagle and Abercrombie & Fitch had their time, but like many things these days, the look is trimmer and more fitted.
Pick up some flat front shorts from Old Navy or Target in a few colors. You'll instantly step up your summer game.
11. Long Sideburns
Long sideburns started becoming stylish in the mid to late 90's right around the time every guy had a goatee. Hair was longer and styles were different, it's time to trim those chops. The longest your sideburns should be with most haircuts is 3/4th the way down your ear. Shorter is good too, just don't do a straight-across. Unless you're going for a specific look, this is a good rule to go by.