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.
Graphic Tees
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?
Baggy anything
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.
Shorts
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.
Flip Flops/Sandals
Unless you’re at a body of water, get rid of them.
Unkempt Haircuts
An adult ensures he always looks good, and that definitely goes for your hair.
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!
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.
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.
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.
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.
The weather is warm and that means it’s the right time to rethink your sock strategy. Also known as loafer liners or loafer socks, no-show socks are a a key warm weather shoe accessory. But, there’s a right way and a wrong way to go “sockless” and wearing no-show socks the right way is an important skill to master.
In this week’s 2 Minute Tuesday we’re answering a question about when and where men should wear no-show socks! Don’t forget to check out our favorite no-show sock picks below.
The Weather Should Be Warm and Sunny
As you can probably imagine, no-show socks are best worn when the weather is warm and sunny. It’s not as much a seasonal thing as it’s warm nearly year-round in places like Florida and California, but more of a temperature and outfit thing (more on that in a second).
Wear Them When You Are Showing Some Ankle
The key thing to know about no-show socks is that you want to wear them any time you’re showing a bit of ankle. So if you’re wearing a shorter hem, cuffing your chinos or jeans, or wearing shorts, you want to wear the right pair of no-show socks. If you’re going with a standard hem length there’s no need to wear no-show socks, just stick to standard dress socks. No-show socks look great will all outfits from shorts to suits, so you can feel comfortable wearing them with whatever you’ve got on. They definitely add a bit of informality to the mix so be aware of that if you’re getting dressed up.
This season, I wanted to break up my annual gift guides by price and gender, so in this one, I want to talk about the gifts under $200 for the various men in your life.
Essentials Box
My all-time favorite company for ties and pocket squares has this great Essentials Box that includes ties, pocket squares, socks as well as tie bars & collar stays for the man who likes to class it up or needs a little help in the accessories department.
For someone into cocktails, this is a great addition to their bar that they might not have. It’s easy to give glasses, stirrers, shakers or booze, but a clear ice cube maker kit is a cut above the standard items one would give.
I’ve gone over the best backpacks or rucksacks before, and my top choices are definitely pricey, but for an everyday, go-anywhere, do-anything bag, this one is my top choice. I love that it comes in different colors in case your recipient may prefer something other than black.
This season, I wanted to break up my annual gift guides by price and gender, so in this one, I want to talk about the gifts under $50 for the various men in your life.
Keyring Multi-Tool
Every man will find this handy, regardless of his age or occupation. I like it because it easily fits on a keyring and is super convenient.
A humidity sealed pack with two cigars, a cutter, and matches for the aficionado, or those who’ve yet to be initiated into the cigar world. You can pick these up as either single purchases, or a part of a monthly subscription. Dorian has spoken to the CEO a few times and has sampled a few of their packages and says they’re top-notch.
This unique leather keyring will keep up to 7 keys all organized and silent within its cowhide leather sheath in your pocket. Like I mentioned in my Accessory Essentials Series, use quality items and you’ll thank yourself (or the man you give this to will thank you, hopefully).
It’s one of those things that most men don’t think of buying for themselves but will use way more often when they actually have it in their grooming kit. It seems weird, but a lot of clients have commented about it being one of the best sleeper-hit style gifts they’ve ever received.
Charging cables can be a boring necessity, or they can be a classy addition to a man’s Everyday Carry. I’d suggest getting a 10ft cable – the extra length comes in way more handy than you’d think.
One might think this is a boring choice, but if you haven’t tried the best men’s socks yourself, you’d be dead wrong. Give the gift of amazing comfort and a lifetime warranty with these awesome socks.
Hailed as one of the best ways to make a single serving coffee, I’ve gifted this to quite a few people who are into coffee and it’s been a success every time.
In this video, I talk about the 21 things men should never wear! These are the things that’ll curl your toenails, and offend even your grandmother. Just don.do.it.
If you’ve downloaded any of my Free Ebooks, then you already know I’ve got some pretty strong opinions about socks – especially white ones. Most of my clients come to me with a drawer full of white, mid-calf length socks, possibly some ankle socks thrown in there, and a ratty pair or two of dress socks they pull out from time to time. This is unacceptable and frankly… gross. Before I took my nephew George under my wing, his sock drawer looked like this, but he had an excuse – he’s a little kid!
Socks area one of the few items in menswear when it’s perfectly acceptable to go absolutely crazy without looking ridiculous. You can use them to show off some of your personality and have fun with them. I’ve got clients who wear their favorite sports teams, crazy patterns, super heroes, etc. People will only really see them when you’re seated and they’re great conversation pieces, so I say go bonkers with them!
The Cardinal Sin of Socks
The only rule you cannot break from this day forward is: NO WHITE SOCKS – EVER. That’s it. They’re the cancer of the sock world. There’s no excuse or reason for owning any white socks anymore.
How many Socks Should I Own?
How many plain & patterned dress socks to have depends on what you wear and how often. I would say have enough to get you through a week, so about 7 pairs.
Best Material For Socks
Socks come in all sorts of fabrics/materials – wool, cotton, cashmere, silk, nylon or blends of each. In my experience, merino wool and cotton blends are best, because they’re more forgiving and comfortable than the other fabrics. They also look great and can be worn with both casual and dress outfits, and they’re just the right thickness. My choices at the bottom of this page will come in either fabric or one or the other. Silk, silk-blended or nylon-blended socks can only be worn with suits and dress shoes and will wear out quicker than other fabrics.
The types of socks to own
Plain & Patterned Dress Socks
I say dress socks, which are usually thinner than regular white socks, but I really just mean colored socks of any material. Think of these as your replacements for your white socks.
Like I said, it’s perfectly acceptable to go crazy here, but you should also at least have the standard colors of Black, Gray/Charcoal, and Navy in your sock drawer. That way, if you’re going to something where maybe it’s not appropriate – like a funeral or when it’s best to be more conservative.
As for material, like I said in the materials section, stick with merino wool or cotton blends because they’re most comfortable and can be worn with casual and dressy outfits. Just beware: Thick cotton or wool socks looks horrible with suits because they’re just too thick and informal. So if you need socks like that, wear them with casual outfits only.
Ankle Socks
These are to be worn when working out ONLY.
These are sometimes called low or short socks, depending on the company. Either way, they should have a little lip at the top. Anything higher, is to be avoided.
As for color, stick with black. White or other colors will get dirty and look gross very quickly.
For materials, merino wool or cotton blends are best.
You want to go with black because it’ll look the best the longest. You can also go with patterns and other colors, but no one will really see it, so it’s a bit of a waste. If you’re wearing white shoes, you can wear white ones, but they tend to get gross and nasty pretty quickly so I just avoid them. Whatever you do, don’t get nude-colored ones. It’s really gross looking.
How to match socks to an outfit
Patterned Or Colored Socks
(Any colors or patterns outside of the standard colors I listed above – black, charcoal & navy.)
The best thing to do, and what I do with my clients, is have a color in the socks, regardless of whether they’re plain or patterned, that is similar to a shade of any item in an outfit – whether it be your shoes, pants, shirts or accessories.
So if your tie or pocket square has a bit of blue in it, wear some socks with blue in them.
Just don’t match your socks to your shirt color if it’s white. Again – NO WHITE SOCKS!
Standard Plain Colored Socks
(Black, Charcoal & Navy)
Jeans and any color sneakers = any of the 3 standard colors.
Black suit (you better be wearing black shoes only!) = black socks
Navy suit (shoe color doesn’t matter) = navy or charcoal socks
Gray suit w/ black shoes = charcoal or black socks
Gray suit w/ brown shoes = charcoal socks
With that said, though, you shouldn’t worry about matching 99% of the time, though, because socks are one of the few places in menswear when you can (and should) go absolutely bananas.
When should you replace your socks?
When they’re worn thin in certain areas – usually around the heel or toes.
When they’re faded, stretched out or stained.
When they’re severely pilled (those weird little balls of fabric usually around worn areas are called pills). Pilling is usually the beginnings of them starting to get worn out in that area.
The Best Men’s Socks
Plain & Patterned Dress Socks
Darn Tough
They’re some of my client’s favorites – and mine, of course. They’re soft, super comfortable and about as durable as any socks I’ve encountered.
The kicker is that they come with a lifetime warranty, so if anything happens to them, send the company an email and they’ll replace them free of charge, for life. Obviously, this comes at a price, because they’re not cheap, but I don’t find the price too offensive compared to other brands that don’t offer a lifetime guarantee.
They’re a merino blend, so they wick sweat and moisture away from your feet, keep them cool in the summer and warm in the winter. They’re also seamless on the toes, so you’ll never have to deal with the discomfort of excess fabric around your toes.
Their cushion versions are the best, but even their non-cushioned socked are great. I found the other sizes, like their micro crew, to be too short and you’ll be flashing some shin when crossing your legs – which is to be avoided – so stick to the crew length or mid-calf lengths.
The only annoying thing is that they don’t sell socks directly, so you have to get them via third parties, like Amazon, REI or GearX
Uniqlo
If you want a great budget-friendly cotton options with LOTS of different colors and patterns, look no further than Uniqlo’s Crew Socks.
Kirkland & Gold Toe
These are good for plain/traditional colored socks. Unless you’re a member of Costco, you won’t be able to get the Kirkland Signature Cushioned socks.
Gold Toe’s are the old standby and are great for their price, but you’ll be replacing them once ever six to 12 months.
Ankle Socks
Just like with their dress socks, I really love Darn Tough Ankle Socks. They’re comfortable as hell and come with that amazing lifetime guarantee.
For budget-friendly and variety, almost nowhere beats Uniqlo. They call their ankle socks “short” socks.
No Show Socks
I honestly say get the cheapest ones you can find because they’re all very similar. Some companies sell cotton blends and others sell more thin, nylon blended socks.
Some clients prefer one type over another, some like to have both and wear the thinner ones with dress shoes and the thicker ones with sneakers. This one is up to you, so try both and see what you prefer!
