When I see photos I took with friends from 10 years ago, I can’t imagine wearing some of the things I wore back then (even though I looked good and dressed stylishly).
I even catch glimpses of stuff I wore 5 years ago and think, I’d NEVER wear that today.
Has that ever happened to you?
Assuming you’re conscious of your style and working to improve it, this is a good sign. It means your look is evolving and you’re dressing sharper. You’re figuring out the “personal” in personal style.
What if you’re feeling stuck and need a bit of inspiration to shake up your current look? Try one (or all) of these 5 men’s style upgrades to get you headed in a new direction, fast.
Upgrade 1: From ballcap to fedora
Yeah, a fedora! That’s right, I said it.
Fedoras may seem intimidating. Actually, any brimmed hat seems intimidating if you’re not used to it.
Nothing feels right at first; you have to sit with that discomfort and wear things a few times (OK, many times, and consistently) to get used to them.
Put those fears aside and dive headfirst into some grown man hats. Contrary to what you may think, you can wear fedoras casually (with denim and military jackets, for instance) just as easily as you can formally.
By the way, don’t get it twisted.
I’m not saying to throw away all your snapbacks and 5-panel caps and replace them with fedoras. I still wear these types of hats myself, and you can still wear them, too. I’m simply suggesting you expand your style options a bit and try things that may be new and unfamiliar to you.
Wearing a fedora is a small style upgrade that can elevate your look and make any outfit interesting without it feeling like some huge shift (like going from T-shirt and jeans to suit and tie everyday would feel).
Check out my guide on how to choose and wear a fedora here.
Upgrade 2: From basic belt to holeless belt
A few years ago, I got my first holeless belt from
Before then, I often found myself in between belt holes. One would be too tight, the next one down, too loose. And if I had a big, coma-inducing lunch, forget about it. Loosening my belt one notch would mean hiking up my pants every few minutes.
There was never any middle ground.
With the Anson belt, I can micro-adjust… a fancy way of saying, instead of having 5 holes spread an inch or so apart, I can adjust the belt in ¼” increments (~6mm).
The built-in track system allows for easy tightening and loosening without any holes. If I need just a smidge more tightness, or I need it to be a tad looser after a big meal, easy!
Side benefit: No wear and tear on your belt from all that tugging and pulling.
Worn out belt = terrible look
Regular belts can look old quickly with all that fastening and unfastening every day. You never have to worry about that stress on the leather with Anson belts.
After getting my first one in brown leather, I immediately ordered 3 more: saddle tan leather, charcoal grey canvas, and camo canvas (for fun, heh).
Anson has a killer box set deal: For $99, you can get 3 straps and 2 buckles, or 2 straps and 3 buckles.
For comparison, one Anson belt on its own is $50, but with the box set, you effectively get 6 belts with all the different buckle and strap combinations you can put together.
The power of multiplication!
Espresso Veg Tan Leather Anson Belt with Antiqued Buckle
Literally the only belt I wear since I first discovered them, and I’m not just saying that.
Even if you can’t get on board with any of the other upgrades I mention here, this is the one I suggest you adopt right away!
Upgrade 3: From dark denim to solid black denim
I’ve been talking about dark blue denim for years, and yes, I still think it belongs in your Lean Wardrobe.
But you probably have a pair or two by now, and if so, you’re most likely looking for other options to add a bit of variety into your outfits.
Enter the solid black denim. My favorite pair is the Levi’s 541 (I mention why here) but you’ll have to find the pair that works best for your body type.
As far as styling a pair of solid black denim, just wear them like you would your dark blue pair. They go with all the same outfit choices, and more. But black denim is much more sleek and looks great with a number of different looks!
Here’s a sample of my favorites.
Monochrome: Black Denim from River Island, Black leather jacket from Allsaints, grey T-shirt from J.Crew, white sneakers from Nike
Smart Sharp Casual: Black Denim from River Island, white dress
Easygoing Casual: Black Denim from River Island, white and blue striped long sleeve
A pair of solid black denim is super versatile as well as a nice change from dark blue denim.
Upgrade 4: From boat shoes to loafers
If you’re on a boat, stick with boat shoes. But if you’re landlocked, try a sleek loafer instead.
Again, nothing wrong with boat shoes (or any of the “from” pieces mentioned here), but the point is to get you outside your comfort zone and trying new stuff that’s a bit more unique and polished.
Going from boat shoes (that every guy everywhere is wearing when spring hits) to a nice loafer is definitely an upgrade.
There are plenty of options, from Waspy penny loafers to sleek Italian horsebit loafers.
If I’m going casual, I like the Sedona model from Allen Edmonds with the tan leather and Vibram sole, or these green suede loafers from Jay Butler. For a dressier loafer, I prefer these tasseled loafers, also from AE.
Upgrade 5: From baggy hoodie to slim crew neck sweatshirt
I get it. You love your hoodie.
It’s oversized and comfy and you like bumming around the house with it. Fine.
The oversized baggy hoodie is even sorta “in” right now (Yeezy taught me).
That’s great and all, but if you’re not 100% all in on a streetwear look, you’re probably not doing it right, and that ratty college sweatshirt you wear around the house isn’t the same thing.
So if you’re going somewhere (yes, even on dumb errands like getting gas or hitting the grocery store), please leave that at home.
Example outfits from Lookastic
If you insist on that “I’m still in my house clothes” vibe but realize you have some self respect, opt for one that fits your body better and has a classic silhouette like this simple crewneck sweatshirt from the . Here’s another option from Uniqlo.
These updated sweatshirts fit slim, look stylish, and have cool details your trusty oversized hoodie from college doesn’t (stains from your last Chipotle burrito don’t count as “cool details”).
Just check out that image above for ways to dress up your slim crewneck sweatshirt. Pretty great, right?
Which Piece Are You Upgrading ASAP?
Is it the crew neck sweatshirt? The loafers? Your belts? Let me know in the comments.
Shout out to Anson Belt not only for making my favorite belt, but for sponsoring this article as well.
And thanks to YOU for checking out the brands and products I suggest.
When you purchase these products, you help support this site which allows me to write more style articles and create more style videos for the Effortless Gent community, which I really appreciate 🙂
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