Upgrade Your Outfits! 9 Ways to Dress Better (in Suits)

When you put together an outfit around a suit, and by that, I mean matching pants and jacket, there are a few things that can help you in most situations to change the look and make it really pop. If you have some basic items in your wardrobe, this post will be very helpful. 

What is a “Basic” Outfit? 

If you have a more contemporary style, a basic look could be a white T-shirt, some white sneakers, and a pair of jeans. For suits, it means a solid navy, gray, or charcoal suit, maybe a white or a light blue shirt, black shoes, and a simple tie. Of course, there are all kinds of other stuff, like socks and so forth. The remarkable thing about the dark suit is that you can really make it much more casual and more formal.

For example, let’s take a look at Preston in multiple looks with one jacket. First, he has the full suit. Then, he has a combination of gray slacks that is more serious; maybe office appropriate. And then, there’s something he could wear at a garden party.

So, today, I started with a very basic outfit. It’s a plain navy suit. It’s a little bit on a lighter side, two buttons, some patch pockets, with a pair of flat-front pants. The material is kind of a hop sack, which is fairly typical of what you would find in a contemporary navy suit. I’ll pair it with a light blue cotton shirt with barrel cuffs and a red silk tie that has a subtle pattern. My socks are solid navy, and my shoes are black cap toe Oxfords with some broguing on them.

I’ll be using this outfit to show you all the different editions and changes, so you can judge for yourself what looks good or what you like, and what’s maybe a little too much or over the top. Always remember, there’s no right or wrong. Style is what you make of it, what works for you, and how you can express yourself.

9 Basic Outfit Enhancements: 1. Tailoring 

The first thing you can do is to go to the alterations tailor. If you’ve watched our channel here, you know we mentioned it many times. It’s simply so true, and so many men still don’t do it. If you have something that fits like a potato sack, but you’re a slim guy like Preston, you want something that’s a bit more trim.

I could go in for hours when tailoring and fit, but we already got you covered. We have a guide that shows you how a suit should fit, another one highlights how a shirt should fit. Also, we have a post that shows you what an alterations tailor can and cannot do.

2. Layering 

The second thing you can do is layer garments, which is quite enjoyable. Adding layers to your outfit makes it literally multi-dimensional. It allows you to add more colors, more textures, more patterns, and it’s like building something like a puzzle or interior design. I mean, honestly, you can take any plain good old suit and turn it into something eye-catching with a simple popping waistcoat.

If you’re out into vests or waistcoats, you can wear an overcoat. Especially if you wear it open, it just adds another texture of layer; maybe you will add a scarf on top of that, and everything looks much more put together.

On top of the patterns, textures, and colors, you also get body. And within the layers, you have the power to make things look more casual or more formal. For example, the navy suit with a moleskin vest in kind of an earthy tone has one look. Compare that to a sleeveless cardigan vest with leather buttons; feels even more casual. A very similar color but more of a finer weave, linen-y wool fabric changes it and looks more formal again.

On the flip side, if it’s like an all-sweater vest with no buttons, it definitely makes it more casual. Likewise, if you add a pocket square to the basic suit, it already looks much more put together, and it’s a simple little piece of fabric. So, we chose a light blue linen one that picked up the color of the shirt. It has slightly contrasting cross stitches on the edge for added visual interest. If you wear an overcoat, chances are it looks better with a scarf. There are warmer scarves, such as cashmere scarves, or lighter ones, such as the double-sided wool silk ones from Fort Belvedere.

Of course, if you are wearing an overcoat and a scarf, you also want to have some gloves. If it’s not really cold outside, go with something unlined. If it’s cooler, maybe cashmere-lined or fur lined. Layering in an outfit doesn’t just showcase your ability to combine different colors and patterns, but it allows you to really expand your wardrobe, because this one basic suit can appear very differently in multiple different situations. So, at the end of the day, you become really versatile. It’s nice to travel with because even though it’s the same basic outfit, it never looks the same.

If you’re, in general, curious about layering and how you can up your game, check out some of our tips on how to layer.

3. Shoe Upgrades

Another great way to enhance a basic outfit is by switching out the shoes. Many men these days wear sneakers with their suits, and we have an entire guide on how and if you should pull that off. Today, I want to stick with the classics.

So, initially, I had this black pair of Oxford shoes; very inoffensive, very business-like. Frankly, in most situations, you don’t really need that look anymore, and you can have a bit more fun. If you’re just starting out and you want to have a lot of versatility, different shades of brown are your friend or burgundy.

We’ve created guides about the first five dress shoes you should invest in that give you the biggest bang for the buck.

To give you a taste of what’s possible, let’s take penny loafers in a medium brown. The outfit looks immediately different. If this is too bold for you, maybe use a darker color.

The suede texture makes it more casual, and the Chelsea boots silhouette, which is a bit shorter than typical Chelsea boots, just adds a cool nuance to the outfit. And a really underrated shoe color is burgundy. Honestly, it works with a navy suit, but also with khakis, corduroys, tweed, and whatever else. It’s dark enough for the office or even an evening occasion, like cocktail attire, but you can wear them very casually, and they never look out of place.

Of course, if you want to go even bolder, you want some navy shoes, olive green shoes, gray shoes, or a pair of spectators. I mean, honestly, the sky’s the limit.

As you know, quality shoes are expensive, and you may only be able to have one or two pairs in the beginning, but you still want to have outfits that look different. The best way to get there without breaking the bank is to invest in different colored shoelaces. You can also have different shapes. For example, you could have the classic round shoelace or you can have flat shoelaces. By adding them in different colors, you can really change an entire outfit. You can make things look a lot more casual, and you can coordinate them with other colors in your outfit. 

Best of all, it’s reversible and if you want to put the black shoelaces in your black Oxfords, they look very formal again. But if you want to have something that pops, maybe something in red will look very different. It’s quick, easy, simple, and affordable. For a selection of great shoelaces. take a look at the Fort Belveder shop.

4. Wristwatches

Time piecing has been elevating men’s outfits for centuries, and while it used to be something like a pocket watch, the wristwatch today is definitely the way to go.

Unless, of course, you’re going for a real vintage look. Wristwatches today are often associated with a certain status or social cachet. That’s probably wearing such a common tool today for drip, flexing, or other trendy terms that really confuse me.

Of course, showing off is not pretty gentlemanly, and if you learn more about what it means to be a gentleman today, we’ve got you covered.

That being said, the reflecting bezel or metal on your wrist can create some visual interest. People who are into watches will definitely identify what you’re wearing, and probably make a form of judgment about you.

Overall, sports watches are really popular today but with this suit, you go with a classic dress watch, and typically, they’re less expensive anyways, especially in a secondary market. Just because the modern James Bond wears a sports watch with his tuxedo because it’s just a huge product placement show doesn’t mean you should. I mean, the original James Bond didn’t, and I think he looked better.

If you’re not sure what type of watch to wear with what type of outfit, we’ve got a guide on matching watches with outfits, which will help you out. 

So, for my basic outfit, if I stick with black shoes, I’d probably go with a black strap watch. I’m wearing an old vintage JLC Reverso. I can also go with something brown. Of course, everyone has different tastes for watches, so whatever works for you is great.

5. Men’s Jewelry

Men’s jewelry has fallen out of favor for several decades, but in recent years, there’s definitely been a men’s jewelry resurgence, and we think that’s a good thing.

With a suit, an easy accessory is a cufflink. Higher-end cufflinks typically are decorated on both sides, but the sky is really the limit, and you’ll go find something that works with your style. Whether it’s a classic design, such as a monkey fist cufflink knot, or some semi-precious stones, diamonds, initials or whatever else, cufflinks will always elevate a suit. Frankly, I know some people who made it even their hallmark to always wear cufflinks with anything they wear, and they only have French cuff shirts. Each to their own.

A very classic item to add is a ring. Either on your ring finger on your pinky ring, some people associate mobsters with it, but if you look at Charles or the English aristocracy, they often wear pinky rings and have nothing to do with a mob. If you’re interested in men’s rings and if you want to understand what the meaning typically is if you wear certain rings on a finger, you’ll enjoy our post here. We also have extensive guides on signet rings and pinky rings, which you might fancy.

If you wear long neckties, a tie clip or tie bar may be interesting for you. Just make sure you wear it in the proper way. In recent years, there was definitely a resurgence of collar jewelry for men. By that, I mean collar bars, collar clips, or collar pins.

Frankly, it’s a relatively small accessory that slightly elevates your tie knot, but it’s pretty cool. If you just have regular dress shirts get a collar clip or a collar pin. If you want to wear collar bars, you need a special shirt that has pinholes for it. Frankly, it’s not so easy to find shirts for collar bars, and often, you have to make a made-to-measure, although these days, there are a few ready-to-wear providers that offer them.

So, for the basic outfit today, I switched my barrel cuffs to nice gold and lapis cufflinks from Fort Belvedere. They have this nice deep blue, which picks up the tone of the shirt, as well as the suit. I also added a nice pinky ring, as well as a gold collar bar. For that, I just switch on my shirt, but I had to do it anyway for the cufflinks. Instead of a collar bar, you could also go with something like a tab collar, and then, in that case, you don’t want a tie that is too big. Otherwise, it just looks unfavorable.

My cufflinks were gold, and so was my ring, so I also chose a gold collar bar, but if I go with silver cufflinks and a silver ring, I would have gotten a silver collar bar, or rose gold or whatever it is. For a selection of collar bars in silver, gold, and rose gold, as well as clips and pins, check out our Fort Belvedere section on our website.

Let’s go to ties. If you have a basic outfit and you just have a basic tie, changing that to a bow tie really changes the entire look, or something with a bit more texture, like a knit tie, for example, like here in this orange, really provides a very different look to your suit.

Alternatively, an interesting silk, such as bourette houndstooth. It’s still a red, but it is distinctly different from these relatively plain silk ties that you could probably buy at Men’s Warehouse.

For my basic outfit, I wished I could have actually used the silk bourette tie in red and white houndstooth, but it was too thick, and it wouldn’t have worked with the color bar, so I stuck to the original red tie, but frankly, I think, overall, it’s a very simple look with red and blue, but I quite like it.

6. Sock Upgrades

Here, I’m wearing navy socks with a navy suit, so you’d think it works together, but if you take a closer look, the navies are not exactly the same. So, it looks kind of off. Socks are really a key element to bridging the gap between your shoes and your pants, and how to combine those three together is an art by itself.

We have an entire guide that will help you to come up with cool combinations.

If you sit or walk, your socks are always visible, and it’s definitely something people will notice. You can also coordinate your socks with your tie or other elements in your outfit, and it creates that harmonious overall look.

Of course, there are more formal options, such as a navy and blue stripe; different but not offensive at all, or there is something more casual like this blue and white version, which I think looks really great with a suede boot, for example. Because I have red in my tie and navy in my suit, I got a mix of both navy and red – works well with the shoes, works well with the pants, and it ties everything together from top to bottom. Of course, there are so many other sock colors out there that you could also use, the creative sky’s the limit here.

If you wear a suit, though, do yourself a favor and get over the calf socks that stay up, because no one wants to see your hairy legs with such a nice garment.

7. Sunglasses

Another thing you can do to make an ordinary suit look extraordinary is to add sunglasses, especially if you’re around outside. Unless you wear glasses regularly, typically, you don’t add much to your face in terms of accessories.

Sunglasses are really a fantastic way to change the look, whether it’s a horn-imitated acetate frame, some classic aviators, modern aviators, Steve McQueen Persols, or whatever other model is out there, it can really change the entire feel of the outfit. Go from trendy, to 80s, to vintage.

Harmonizing the sunglasses with the rest of the feel of your outfit will just make it even more cohesive. People will think, “Man, this guy looks great,” even though they can’t quite put their finger on it. As they start looking they may say, “Oh these socks are cool, or this vest, or these sunglasses,” but at first, they just notice that you’re really well put together.

If you’re not sure where to start with sunglasses, here are some basic styles and tips for face shape and shade style.

8. Hats

Another great way to enhance a classic suit outfit is by wearing a hat. I know not every man is comfortable wearing one, and it’s definitely out there, but if you pull it off and you do so well, it really changes the entire feel of your outfit.

A hat keeps you warm, adds a nice texture, frames your face, and because of that, people like Preston wear one every day when they leave the house. Personally, I’d love to wear them more often, but I have to deal with acne and zits on my forehead. So, I don’t wear them all the time. 

So, if hats make you look so good, why are just so few people wearing them today? Actually, we answer that question in another post.

If you’re interested in classic style, though, no water accessory changes the look and feel of your outfit as much as a hat, such as a fedora. Even if you might feel uncomfortable right now to maybe wear a bow tie or a hat, I encourage you to experiment with it because there was a time when I felt a bow tie wasn’t right for me or a head wasn’t right for me, but once I wore it more often, I actually really came to like it. And whenever I go places, people always compliment me on it.

Where should you start with hats? First, check out the guide on finding the right style for your face shape, and then we’ll tell you how you can pull them off confidently. And hey, if that’s not something that you like, that’s cool too. You can still really enhance the basic outfit without any form of headwear.

So, for my outfit, I could have easily pulled off this navy felt hat with kind of this silverish band, or I could have gone with something brown. Even though the color doesn’t quite match my shoes, overall, having something brown on top and at the bottom ties it all together visually. 

Conclusion 

Looking at the basic navy suit outfit, it started out rather plain. With an experiment with some layering, we added pocket squares, tried on some different ties, added waistcoats, knit vests, and casual vests, but then stuck with the off-white or cream linen. I exchanged the shirt so I could wear cufflinks and a collar bar, which definitely changed the entire look. I also wore a pinky ring, changed my shoes, and upgraded my socks.

Because I kept the red tie, I went with the navy and red socks, I could have gone with the red shoes, but I felt the loafers were just as good of an option. And overall, even though they’re brown, they have a tone of red. If you just quickly glimpse it, it doesn’t feel like the same suit.

I think the vest definitely has the biggest impact because it has the biggest and boldest color but even those little changes, like the socks, may not be something that you see immediately, definitely has an impact.