You just turned 30 or you’re in your 30’s and have decided to get it together on the clothing front. Congratulations because this officially means you’re now a proper grownup. While you may not be be hitting your peak professionally or financially yet, you’re definitely on the way, which means you should be taking your clothing and appearance a little more seriously.
So where does that leave your wardrobe? How do you walk the tightrope that is post-twenties dressing without looking like an over-the-hill has-been, or worse – a textbook case of early mid-life crisis?
These are some of the items that categorically shouldn’t be in your rotation in your third decade. Even if you do feel young at heart.
Dirty or Faded Anything
You’re too old to have an excuse for dirty clothing and shoes. You’re not out in the playground anymore, so your excuse for having dirty or terribly worn out anything is just laziness.
There are two exceptions when it comes to wearing one: You’re headed to watch your favorite sports team play or you’re going to a concert. Outside of these two situations, wearing a graphic tee communicates your someone who can’t get over the fact he’s no longer in his twenties.
Dirty, old or worn out shoes
No self-respecting man should be walking around in old, dirty shoes. Ever. Also, did you know it’s one of the first things women look at and can be a real make it or break it when it comes to first impressions?
Unless you think to yourself, I’d like a more relaxed fit with these because that’s a silhouette I’d like to go for with this outfit, then you shouldn’t be wearing anything ill-fitting. The days of you wearing clothes because they were gifted or somehow found their way into your wardrobe by happenstance are over. A man in his 30’s should know what he’s going for and should nail it.
“If a guy shows up wearing ill-fitting pants or a big shirt, game over,” said every woman on planet Earth.
White socks and novelty underwear
Nothing says this guy dresses like a grade schooler more than white socks. Replace them with literally any other color – starting with black, blue and gray, and you’ll be on the road to adulthood!
Novelty underwear is a rite of passage for most men. When you’re a teenager, it’s the go-to Christmas gift for relatives intent on finding skivvies that’ll give you a chuckle. But we’re still not laughing.
Hopefully by now, you’ll have had the sense to leave the trunks that declare you a ‘Beer Monster’ or baggy boxer shorts emblazoned with the warning ‘In Case Of Emergency, Pull Down’ far, far behind you.
We even did a super in-depth article on the best men’s underwear out there if you need to check that out.
Cargo shorts, especially. The one type of shorts you can wear are chino cloth shorts, but frankly, now that you’re older, shorts should mostly be worn near bodies of water in the form of swim trunks. Instead, grab some chino pants and roll up the hem (or get them hemmed to be a little shorter) and you’ve got something breathable and much more age-appropriate.
Unless you’re at a body of water, get rid of them.
An adult ensures he always looks good, and that definitely goes for your hair.
Sweatpants & Sweaters
These were okay options to wear when you’re in school when studying (and partying) take priority. But if you’re out of school, this look should be relegated to around the house, at most. There’s much better options for loungewear these days, but either way, remove these out of your daily or weekly rotation and start putting together a more adult, Essential Wardrobe.
Jean Shorts A.K.A. Jorts
When you were a teenager these were passable because people assume your parents bought them for you, but those days are over. Instead, opt for some chino cloth shorts, which are more age appropriate and can be styled a bunch of different ways.
Chunky Skate Shoes
Wear these, of course, if you’re still skating. But just like a construction worker should change out of his steel-toed boots after the day is done, don’t wear these outside of their intended usage time and get some stylish low-top sneakers instead.
The days of wearing clothing that doesn’t fit your body are over. Anything big and baggy (that isn’t part of a specific fit) is sloppy and shows poor judgement as a budding adult, so instead learn how clothing should fit your specific body type and get it together.
Wearing hats all day, everyday is a big sign of a young man who still is dressing like a teenager. If you’re wearing hats because you are too lazy to style your hair, then it’s time to find a hairstyle that fits your lifestyle best. Hats should be worn sparingly in the adult world, so find a hairstyle that works best for you.
Unless you’re well off, the stupidest thing to do in your 20’s is get yourself into debt because you want to wear designer clothing. As we work with every major designer in the world, we can assure you that they aren’t worth going into debt for. You’ll absolutely regret it!
Due to the low profile of lowtop sneakers its really hard to mess this up. They’ll work with almost any cut of jeans.
As for denim colors or styles, unless they’re all black sneakers (which we discussed before), you can pretty much wear any color or style you want. The one caveat is that if you’re wearing white sneakers and dark indigo jeans, they can stain the tops of the shoes. So soak the pants in cold water for about 30 minutes to get rid of any excess dye that may rub off on the shoes and then spot clean the shoes, as necessary.
If you want to avoid staining the shoes all together, either get them hemmed or cuff them to not touch the tops of the sneakers. We’ve done a whole article and video about cuffing your jeans here.
If you’re going to buy hi-top shoes and wear them with the hem going past the tops of the shoes, you should just get a lowtop pair of sneakers instead. We’ll assume you are wearing hi tops because you like the look of them and want to show off the whole shoe.
To do this well, either gets your pants hemmed shorter or cut them with scissors for a frayed look to show off the shoes or simply roll them to just below the top of the hi tops. Never more than twice, though, otherwise you’ll have a really thick cuff on the bottom and it will look very heavy and off on your shoes.
There’s two schools of thought here and it depends on how “chunky” the running shoes are. If they’re low-profile and sleek, then stick to a similar cut as low-top sneakers – which means wear any cut of jeans. You can even cuff your pants if you want a sportier look.
If you’re going for the Dad/Ugly sneaker look, then the chunkiness of them dictates you go for a straight leg, more relaxed cut. The more stonewashed, the better!
These will pair really well with dark-wash or black jeans. Just make sure you’re jeans have a slight to no break to match the sleeker and more polished dress boots. Wearing dress boots and stacked hems is like wearing tuxedo shoes with jogger pants – it just doesn’t look good.
These boots tend to have a chunkier sole and more casual appearance, so definitely play up the workwear version and wear them with dark wash denim or denim that has some fading. And cuffed or uncuffed, you can wear them anyway you want. If you’re going for the super slim fit jean and chunky boot look (Justin Theroux), get them hemmed or roll them up to be shorter and leave no break. If you want a super vintage look, then try a single, oversized cuff and a more relaxed fit.
Desert & Chukka Boots
Wear them with any color and cut of jeans you prefer and they tend to look best with a slight or no break, depending on the look you’re going for. You can achieve this by cuffing your jeans or getting them hemmed.
As we talked about in a separate video, Chelsea Boots are not for everyone- if you’re a bigger guy, stick to work boots unless you want to look like Humpty Dumpty with little tiny legs. Chelseas need to be paired with slim jeans to look their best. The color and material of the boots will determine what you should pair them with.
If you’re wearing black leather or suede chelseas, they’ll look best paired with black or gray skinny jeans. Anything outside of this will be much harder to pull off.
For brown or tan suede Chelseas, especially with a gum sole, go with a lighter blue or gray denim, which can also have some distressing.
If you’re going with brown (not tan) leather Chelseas, a dark wash denim will look best since browns and dark denim are a match made in heaven.
Debries & Brogues, Oxfords, Wingtips, Monkstraps (Dress Shoes)
Derbies, like Doc Martins, feature a chunkier profile, so they’re better suited for casual outfits that include denim. Black looks great with black or dark wash denim, while brown looks great with dark washed, stonewashed or even distressed lighter denim. If you want those late 80’s or early 90’s vibes, pinroll your jeans and wear them with white socks (I know we’ve talked about our hate of white socks before, and that still holds true 99.9% of the time. This is literally the .1% of times it will look good due to the specific, era-related look you’re going for.
For Brogues, as a general rule, the sleek, minimally detailed brogues will skew more formal while chunky, hole-punched ones will skew more casual. The color of the shoes affects which jeans your brogues will or won’t work with, going from black at the formal end and getting gradually lighter towards the casual end will work best. Casual tan brogues pair well with indigo or lighter denim while other colors like oxblood and black will look good with black denim. As for cut, they’ll work for any cut of denim you wear, regardless of the length of jeans you wear.
You can pull off Oxfords with black or indigo jeans, as long as they’re slim, and either cuffed or hemmed with no break so they’ll feel a little more casual, but still sleek and polished.
Loafers & Penny Loafers
The penny loafers’ low vamp (that’s the section of upper that covers the front of the foot) combined with a wide leg opening can make your feet look weirdly stubby. So opt for jeans that are tapered and cropped or pin-rolled. As for colors, we love a medium brown pair that goes well with dark wash indigo but can also be paired with any lighter colors up to white denim. Black penny loafers will look great with gray or indigo denim.
They’ve been around for a long time, but have created some dynasties like Air Max, Air Force 1 and Air Jordan, plus classics like the Cortez, it’s hard to dispute them as one of the top sneaker brands right now.
Their classics like the Superstar, Stan Smith and Gazelle always make our lists of top sneakers every year, but they have been innovating the past few years with their 3d printing and sole technology and have to say, HUGE fans of the boost soles. Put them on any shoe and I’ll be interested.
Like Adidas, they will make every essential sneaker video we’ll produce from here til the end of time. How do you deny the All Stars or Jack Purcell’s iconic status?
When they introduced the Achilles Low model in 2004, the men’s sneaker game was officially changed. Soft, Italian leather and a timeless design made them the perfect shoe for anything from a suit to shorts.
Not only are they responsible for some of the comfiest and most iconic running shoes ever made, they’re known for their excellent materials and craftsmanship. They have their classic styles, but have branched out into sleeker options and have also done some really cool collaborations too, that it’s hard to deny they’re one of the best sneaker brands right now.
As we’re from California, these have been virtual staples for us even as little kids, so while it seems like they bubble up in the international consciousness every decade or so, we’ve been seeing and wearing them our whole lives, so they deserve a place on the list for absolute staying power.
Use shoe trees
They keep your shoes odor and moisture free and also help maintain their shape when you’re not wearing them. They’re a great investment that you’ll use for the next few decades, promise. In a pinch, you can also use the original paper inserts.
Favorites: These, or These
Use a shoe horn
When putting on your shoes, if you’re stomping your foot in, or tearing some of the skin off your fingers while using them as a shoe horn, you’re ruining the backs of your shoes, you fingers, or both. Whether they’re sneakers, dress shoes or boots, there’s nothing worse than the backs of your shoes getting wrinkled and faded because you’re not using a shoe horn.
Favorites: Choice #1, Choice #2
Tie your shoes properly
It may sound trivial, but where you separate the men from the boys is by paying attention to the details like how you tie your shoes. So you should definitely learn how to tie your shoes so the laces lay flat, at least, but frankly, there’s an even better solution in the next point.
Hide the laces
Nothing ruins a great outfit more than long, floppy and/or ill-tied shoelaces. What you really should do is hide them and the best possible way to do this ever is by using these special laces we found a few weeks ago that makes laces that are meant to be hidden. You only have to tie them once and suddenly all your sneakers and dress shoes are now slip ons with amazing looking laces. Seriously, they’re game-changers.
Keep them clean
Give them a quick rub down about once a week with a moist rag, sponge or paper towel, or as they get dirty. Then once a month, do a little deeper cleaning with a proper shoe cleaning kit for about 5 minutes once a month. If you’ve got dress shoes, you can also polish them, but typically, a little cleaning every few days goes a long way.
Get Rid Of The Stink
What some people don’t know is that actual smell is bacteria, and it’s living inside your socks, shoes, and on your feet, so it’s imperative that you kill the pesky bacteria before it turns into a foot infection or worse… There’s a spray that is fantastic and kills bacteria in 10 seconds and has a nice citrus smell. When storing your shoes overnight, pop these in them, as needed.
If you have a pair of shoes that you love and fear their eventual demise, the best thing to do is buy multiple pairs of them and swap them out to give them some rest. Coupled with using shoetrees and keeping them clean, your shoes will last significantly longer if you give them breaks between wearing.
Winter can be a tough time for your personal style, plus the weather and elements require special attention for your wardrobe and, more importantly, your accessories. That said, the right winter accessories will bring both function and personality to your wardrobe. It doesn’t all have to be about keeping warm (though that’s definitely important), it’s a great opportunity to add some extra style to whatever you’re wearing. For more basic tips, make sure to check out all of our Winter Essentials and our article on Winter Style Do’s and Don’ts
Here are our picks for the Men’s Winter Accessories That Every Man Should Own!
Cashmere / Wool Knit Hat
A must when it’s freezing. Go for a thicker rib knit and try cashmere for a luxurious touch that’s soft, light, and warm. Don’t be afraid to try a pop of color here too!
A Patterned Scarf
The perfect time to add some color or pattern into the mix. Just a hint of it peeking out from under a coat is a sharp, stylish look. Cashmere is a great option here too, it’s very light and warm.
We’re not talking about thick ski-style gloves, but something lighter but still warm. Look for knit versions in wool or cashmere or lined leather options for a sharp touch (especially if you dress up often).
Add in a thin watch that toes the line between dressy and casual so you can dress it up or down. Layered and formal outfits need a watch that’s not big and bulky. Wearing a big, sporty watch with dressier looks can just throw off the proportions. Luckily our friends at Nove watches have the perfect styles. Their watches are high-quality, Swiss-made, and come in a variety of slim styles that work well with a range of looks. Plus, we’ve got a special deal for you guys. Use offer code AW20 for 20% off your purchase.
Picks (from the video):
Merino Wool Socks
Merino wool has incredible technical properties (warm, lightweight and dries quickly) and there are great options out there that are lightweight, warm, and stylish.
We discussed in our Winter Do’s and Don’ts, and the right pair won’t be bulky or too hot and can easily layer underneath both casual and dressy clothes. We really like our go-to pick below because they are very light, warm, and won’t break the bank.
Extra-moisturizing skincare products
Nobody likes the look of dull, dry skin and the cold, dry air can be brutal on your hands and face so take extra care to moisturize properly. The right products and a solid morning routine and evening grooming routine will really help keep your skin looking great during the winter.
Leather Lace-Up Boots With A Rubber Sole
Proper boots for the winter are crucial and if you’re dealing with a lot of rain and snow you want to make sure your boots are protected and have a rubber sole for traction and durability. Some of our picks below have a Dainite sole which is the gold standard in terms of protection and grip in wet, snowy conditions.
Dorian’s Outfit Details
Winter can be a tough time for your personal style. Cold weather and the elements can lull you into just giving up, but don’t do it! These few simple tips can keep you looking sharp and feeling great, no matter how cold it gets! For more tips, make sure to check out our Fall/Winter Essentials Series!
Here are our Winter Style Do’s and Don’ts!
Winter Style Do’s
Do Add Some Colorful Jewel-toned Accessories
The right hats, scarves, and gloves are crucial for warmth and style. They’re also a great opportunity to add some color and pattern to brighten up your look. Colors like emerald green, a mustardy yellow, dark purples, reds, and blues are all easy to incorporate into your winter wardrobe and pack a stylish punch of color.
Do Invest In Quality Outerwear
We talk a lot about where and when to invest, and outside of dress shoes & boots, outerwear is the other major area we really recommend investing in. You get what you pay for and with the right investment, a high-quality coat, peacoat, or jacket will last for years to come, keep you warm, and have you looking stylish.
Do Get The Right thermals
There are many great brands offering very thin/lightweight thermals that’ll layer comfortably underneath your clothes and keep you warm. The key is to get a trim fit, that way they’ll lay flat and layer easily under everything from jeans to suits. Our pick below is light, warm and you can wear these as a base layer underneath your clothes or on their own as a long sleeve shirt.
Winter Style Don’ts
Don’t Neglect Your Skin
You may not think so, but cold-weather skincare is just as important as warm weather skincare. The cold, dry weather can be incredibly harsh on your skin and strip away it’s protection, so it’s super important to cleanse and moisturize properly and stay hydrated. There’s nothing more distracting and unattractive than dry, dull skin.
Luckily, our friends at Geologie have you covered. Geologie puts together a simple routine formulated for daily use. The products are personalized to your skin’s needs and work great for every skin type. We tested out their set that comes with 4 different products: Everyday Face Wash, Vital Morning Face Cream w/ SPF, Repairing Night Cream & Nourishing Eye Cream. It even includes 2 bottles of face wash, one for your sink and one for your shower or to take with you to the gym. Plus, just for our readers and viewers, you can get 30% off your purchase with code Ashley30! Shop here and enter the code at checkout.
Don’t Forget To Layer
We talked about it for Fall, and it’s just as applicable in Winter. Proper layering can help you regulate your temperature and look stylish no matter how cold it is, making sure you’re comfortable going from the cold outside to warm inside (subway, office, etc.).
Don’t Forget To Winterize your boots
Boots are essential footwear for Winter (our go-to picks for this year are right here) and the right pair can look amazing and last a long time. But, you’ve got to prepare them with the right leather treatments to keep them from getting ruined in the inclement weather.