7 Details that Make or Break an Outfit – Tips for More Stylish Menswear Looks

When you buy something using the affiliate links on our site, we may earn a small commission.

While it may seem simple at first to put together menswear outfits (especially if you’re working with something like a suit, which has a matching jacket and trousers), how good a finished outfit looks can actually come down to some of the smaller details! Read on to discover seven such details that can be “make or break” features of an ensemble.

When you consider all of the different individual pieces that come together to make up even an everyday look, the prospect of putting together a truly polished outfit can start to seem a bit more daunting, but these tips will surely help you to more confidently assemble your outfits.

7 Details that Make or Break an Outfit

Break an Outfit #1: Matching Tie and Pocket Square

The first detail that can break an outfit is to wear a tie and pocket square of matching material. Whether you’re shopping online or in a department store, it can be fairly easy to find tie and pocket square sets that make both pieces from the same fabric. However, wearing these together is usually the mark of a man who’s just getting started on his menswear journey. There are multiple reasons why wearing ties and pocket squares of the same fabric don’t create a good look, and the first is that there isn’t going to be enough of a pleasing visual contrast between the two accessories.

Matching tie-and-pocket-square sets are sartorially uninspired and often made from cheap fabrics).
Matching tie-and-pocket-square sets are sartorially uninspired and often made from cheap fabrics).

Also, consider the idea that human bodies are naturally slightly asymmetrical, as are suit jackets–or any other kind of jacket, for that matter–because there is only a breast pocket on the left side (though it can sometimes be found on the right side). If you’re wearing a tie and pocket square of the same fabric, you’ve got that element on both the center of your body and on one side, but this reinforces the asymmetry because there isn’t also a matching element on the other side of the body.

matching tie and pocket square
Wearing a tie and a pocket square with the same pattern reinforces the asymmetry on your body.

But, given that the jacket’s breast pocket is largely decorative it would probably look silly if a jacket were to have two breast pockets and indeed if you were to wear two pocket squares at the same time. As a supplementary point here, the ties and pocket squares that are often sold in these sets are typically made from lower-quality materials like synthetics and polyester and are often in overly shiny satin finishes that typically just look cheap. As you might expect, the root cause of this is manufacturers trying to cut costs by using more of the same fabric.

Make an Outfit #1: Complementary Tie and Pocket Square

To change this around and make your outfit, wear a tie and pocket square that while not exactly the same, do work to complement one another. And indeed, if your chosen styles are either simple classic or both, choosing ties and pocket squares that work well with each other can be a fairly easy task.

A well combined pocket square and tie will definitely earn you compliments.
A well-combined pocket square and tie will definitely earn you compliments. (tie, pocket square, and boutonniere from Fort Belvedere).

In the broad strokes, the main point here is that if you’re wearing both a tie and pocket square, you should try to make one of the accessories bolder and one a bit more grounded and neutral. Furthermore, if one of the accessories has a color that the other accessory picks up on, they will be harmonious and working in tandem.

A gray suit paired with a red pin dot tie, white collared shirt, a white pocket square and a white pocket square.
Stylish combination: Silk Tie in Jacquard Burgundy Red with White Polka Dots paired with a white pocket square.

Nine times out of ten, if you’re in doubt about how to combine a pocket square with a tie going with a simple white linen square, is almost always a safe bet. As an extra point here: if you do happen to have some of those matching tie and pocket square sets sitting around, try to mix and match the ties and pocket squares instead of wearing them in their original matching sets.

Break an Outfit #2: Sneakers with A Suit

Over the last two decades or so, as attitudes about suit-wearing have gotten more informal and more creative, a growing trend has been for men to pair sneakers or other types of sports shoes with their suits. This trend is often discussed in menswear magazines or in online forums as a great way to dress down a suit, but in our estimation, the difference in formality between a conventional suit and a pair of sneakers is just too great, and the overall effect is, again, disharmonious.

Wearing a pair of sneakers with a suit looks disharmonious in our estimation.
Wearing a pair of sneakers with a suit looks quite disharmonious in our opinion.

Of course, there’s nothing wrong with having a pair or two of sneakers in your wardrobe to wear with other more casual ensembles. What we’re simply saying is that you shouldn’t attempt to wear sneakers with more formal ensembles like full suits.

Make an Outfit #2: Go with Classic Dress Shoes

We believe that the ideal companion for a suit and a way to make your outfit is to pair it with a pair of classic dress shoes. Indeed, classic dress shoes transcend fashion to always be in style and if you’re wearing a pair of dress shoes that are well made with quality materials on a classic last shape that fits your foot, they can even be more comfortable than sneakers.

Invest in quality dress shoes - not only that they pair well with a suit, they would also last you for a long time.
Invest in quality dress shoes – not only that they pair well with a suit, but they would also last you for a long time.

Furthermore, if you know how to polish and maintain them a quality pair of dress shoes will probably last longer than a pair of sneakers in the long run as well. Applying the right kinds of polishes and creams, using shoe trees, and alternating the days on which you wear a given pair of shoes will help to extend its lifespan.

If you form a good relationship with a local cobbler you can get your shoes resoled to extend their life even further. This is because the soles of quality dress shoes are stitched onto the upper rather than being glued or cemented as is more common with other more casual shoe styles.

A classic pair of dress shoes is the ideal companion of a suit.
A classic pair of dress shoes is the ideal companion of a suit.

If you’d like to change up the look of your shoe or be a bit more playful, changing the laces is a great way to do this. If you’re new to building a dress shoe wardrobe, we have a list of 5 essential dress shoes to get you started. 

Break an Outfit #3: Dress Shoes with Gym Socks

Similar to sneakers, the origins of gym socks lie in their use for sporting or athletic type events only and they’ve only become more popular in everyday wear as things have become further casualized. However, also in a similar fashion to sneakers, they shouldn’t be paired with formal outfits.

A pair of white gym socks doesn't combine well with formal outfits.
A pair of white gym socks doesn’t combine well with formal outfits.

Not only is there a clash in the relative formality between your shoes and socks in this case, but also gym socks are typically woven in a chunkier style so they can make your feet hotter and sweat more when they’re in dress shoes and indeed, can actually distort the shape of your dress shoes over time.

Make an Outfit #3: Go with Over-the-Calf Socks

The better choice for pairing with your dress shoes then is a quality pair of over the calf dress socks. Socks like these, such as the ones that we offer at Fort Belvedere are made from finer cotton and thus regulate the temperature of your feet better allowing them to breathe more and sweat less.

Navy Blue and Red orange Turquoise grey charcoal Ribbed Over the Calf Socks with Shadow Stripes Cotton Fil d Ecosse - Made in Italy by Fort Belvedere
Over The Calf Shadow Stripe Ribbed Socks by Fort Belvedere

The finer cotton will also feel somewhat like a second skin remaining comfortable all day and not bunching up. Furthermore, if they’re worn in an over-the-calf style, they should stay up all day instead of sliding down.

Break an Outfit #4: Too Many Accessories

There are a wide array of different accessory choices in the field of classic menswear and especially for those who are just getting into the hobby, it can be tempting to load up your outfit with as many different types of accessories as you can get your hands on. However, there comes a point where the cumulative effect of all of this hardware is just going to look too crowded, loud, and flashy like a cry for attention.

Having too many accessories in an outfit will look too crowded, flashy, and cry for attention.
Having too many accessories in an outfit will look too crowded, flashy, and cry for attention.

Furthermore, all of these individual accessories are probably going to end up fighting with one another for visual control of the outfit and the overall effect will simply look too busy.

Make an Outfit #4: Fewer, Refined Accessories

The seasoned gentleman will add a tasteful amount of accessories as and when necessary to complement the rest of his outfit. Essentially, think of your overall approach to accessories as being in quality over quantity mindset. Well-made metal jewelry in particular will get better with age as it develops a slight patina that will provide a unique bit of personality just to you.

Have a quality over quantity approach when it comes to accessories.
Have a “quality over quantity” approach when it comes to wearing accessories.

Break an Outfit #5: Wearing Suits with T-shirts

Our fifth outfit breaker today is another more modern trend: pairing suit jackets or indeed full suits with t-shirts underneath. In fact, this trend is often paired together with the sneakers and suits trend we discussed earlier. As a point of clarification, what we’re referring to specifically in today’s post is pairing t-shirts with full suits.

David Gandy
A sport coat could be a better option if pairing with a t-shirt, as David Gandy shows here.

While we do believe there might be the occasional time and place where an odd jacket could be pulled off with a t-shirt style, the clash in formality levels between a t-shirt and a full suit is, in our opinion, just too great.

Make an Outfit #5: Wear a Dress Shirt

It should come as no surprise that what we would suggest being worn under a tailored jacket of any style is a proper men’s dress shirt. The structured collar of a dress shirt is going to frame your face well regardless of whether you choose to add neckwear or go without and simply leave your top button unbuttoned.

Preston in a dark brown patterned suit jacket, white collared shirt, and accessories from Fort Belvedere.
Formalize your outfit with a collared dress shirt and tasteful accessories

And, while a t-shirt is typically a short-sleeved option, a dress shirt with long sleeves should show a bit of shirt cuff over the edges of your jacket sleeves, providing more balance and harmony to the outfit. 

A beautiful OCBD by Turnbull and Asser
A beautiful OCBD by Turnbull and Asser

If you are looking to tone down the formality of an overall look, we would suggest a smart choice would be an Oxford cloth button-down shirt. This shirt style is a classic and timeless option that’s been worn by stylish men for decades, and while it is a bit more casual, having its roots in Preppy, Trad, and Ivy styles, it isn’t going to create as stark a contrast as a t-shirt would.

Break an Outfit #6: Poor-Quality Fabrics

In today’s retail landscape characterized by fast fashion, the need to get new looks and styles out every season means that most manufacturers and retailers are going to try to cut some corners in order to get goods out as quickly as possible.

And, time isn’t the only factor here as retailers want to offer a wider range of products to consumers at a seemingly overall lower price.

$100 Polyester Fabric
Garments made from synthetic fabric materials like polyester are usually sold at a much cheaper price.

What both of these factors contribute to then is that especially in the fast-fashion world, most garments today are going to be made from lower quality fabrics. Polyester, nylon, and other synthetic materials are fairly cheap to produce thus they are priced by manufacturers as being low cost.

However, synthetic fabrics tend not to breathe well which will increase your body temperature, might make you sweat more, and is going to make you less comfortable overall. And while some retailers might try to game the system a bit by blending synthetic materials with natural fibers, the laws on how this must be displayed on tags or marketed on websites can vary from location to location.

Other manufacturers, on the other hand, would try to up the game by blending synthetic materials with natural fibers.
Other manufacturers, on the other hand, would try to up the game by blending synthetic materials with natural fibers.

For example, a garment might be able to be sold as premium cotton but looking at the composition tag will show that there’s actually a mixture of different elements. And, while you may pay less for a synthetic or other low-quality fabric garment at first, the fact is that these cheaper materials are going to discolor, stretch out, and wear through faster than a natural fiber, meaning that your overall cost per wear metric is probably going to be higher in the long run.

Make an Outfit #6: High-Quality, Natural Fibers

To make your outfits and indeed your wardrobe better overall then, we would advocate for buying garments that have high-quality natural fibers whenever possible. With the right care and attention, garments made from natural fibers are going to last longer and look better than their synthetic counterparts and indeed, this is evidenced by the fact that you can find so many natural fiber garments available in vintage and second-hand stores.

Raphael and Preston search clothing racks in a vintage store.
Raphael & Preston on a vintage hunt

Whether you’re purchasing pre-owned or new, garments with natural fibers are going to have a longer lifespan and thus a lower overall cost per wear, and natural quality fabrics are going to look fantastic too, as they’ll have natural finishes or textures that will add a sense of refinement to your outfits.

Break an Outfit #7: Poorly Fitting Clothes

Finally today, our seventh outfit breaker is one that we’ve discussed many times on the website: wearing poorly fitting clothes. As we’ve said many times, no matter what the fabric quality of a garment is, if it fits your frame poorly, it’s still going to lead to a sloppy look overall.

Regardless how stylish your outfit is, it would still look sloppy if the fit is not right.
Regardless of how stylish your outfit is, it would still look sloppy if the fit is not right.

Of course, it can be tempting to purchase an ill-fitting garment especially if it fills a gap in your wardrobe, is well-made, or if it’s on sale.

50% Suit sale
Don’t be taken in by a flashy sale offer; unless the garments are of high-quality and fit you well, no discount will be worth it!

If there’s a particular brand cachet associated with the label, this might also be an incentivizing point but even if you do have a loyalty to a particular brand or think that displaying their logo will earn you respect from your peers, this is not going to have the desired effect if the garment is indeed ill-fitting. And as we’ve said before, just because an item is discounted or on sale, doesn’t mean you should buy it if it’s not going to fit you.

Make an Outfit #7: Know Your Proper Size

The best course of action, then, is to know your measurements and your typical sizes in various garments, as between different brands sizes can actually vary a bit and how they’ll fit on you even if their numbering is the same.

Know your measurements; everyone has their own unique build
Know your measurements; everyone has their own unique build

Even if you do know your sizes and measurements and can buy garments off the rack that fit you reasonably well, an even better choice is to take them to a skilled alterations tailor to get the fit that much more exact.

Even if you know your measurements, it's also a good idea to take them to a skilled alterations tailor to get the perfect fit.
Even if you know your measurements, it’s also a good idea to take them to a skilled alterations tailor to get the perfect fit.

Seemingly small tasks like hemming a trouser leg, taking in the waist of a jacket, or adding darts to the back of a shirt can have a large effect on how a garment fits you and indeed how it contributes to your outfit and overall look. Of course, it will help if the garment generally fits you well to start with as even a skilled tailor isn’t going to be able to make a garment fit you if the size is much too big or too small to start out with.

Conclusion

We hope our rundown of these seven details has been helpful for men who are just starting out on their style journey and even for those seasoned clotheshorses who just needed a bit of tuning up. If you’d like to learn about even more common men’s style mistakes you can get the top 15 just by signing up for our email list and our E-book with the top 50 is available in the Fort Belvedere shop.

Have you fallen prey to any of these “outfit breakers” in the past! Share with us in the comments section!

Reader Comments

  1. In case anyone is wondering about the placard in the Russian shopping mall at 1:22: it says “зимние скидки,” which means “winter discounts.”

    On no. 6: Another reason to avoid garments of synthetic materials is that the production and even the washing of them introduce non-biodegradable pollutants, such as microplastics, into the environment.

    1. I agree with the environmental impact of synthetic fabrics. Also, cheaper “fast fashion” items made with low quality fabrics are also more likely to be made in factories with poor labour conditions. We recently had a case in the UK where garments made for online fashion retailers were made under conditions of modern slavery. Meanwhile, if you form a relationship with a local tailor, you know exactly where your clothes come from and who was paid to make them. I’d love to hear the experts’ view from GG on sustainable choices when building my wardrobe!

  2. I always enjoy reading the articles that Gentlemen’s Gazette produce on sartorial elegance however, I do take exception to your views on ties and handkerchiefs made of the same material. I have been displaying handkerchiefs in my top jacket pockets for many a long year and if the tie and handkerchief aren’t made from the exact same material they are always a colour match. I always sport silk handkerchiefs as I maintain that they look superior to any other material that one could choose for this purpose. I would contend that the 4th image in this article (red tie with white handkerchief that had red piping)looks more like someone who was starting out with their menswear journey than someone whom has specifically chosen 2 items of apparel that are designed to go together.
    I do agree with the other points made in this article although as I do not like wearing socks I don’t no matter what I am wearing saving for when it is very cold as it is today here in the UK.

    1. Hi Shaun,
      To each their own. Having seen plenty of matching pocket square-tie sets in my younger years, I used to think they had to be colour matched. In my 30s I don’t necessarily think it’s the case, especially after having seen this video clip by Antonio Centeno at RMRS. Some of the combos he’s showing (like everything else) I’m not so keen on (especially complete contrasting colours and patterns) but otherwise I think this video has ‘sold’ me the idea about complimentary colours. It also shows more examples of how different patterns work together: https://www.realmenrealstyle.com/tie-and-pocket-square/

      Different materials are fine, good even because they add texture to an outfit.

      1. Perhaps the reason you saw so many matching ones in your younger years was due to so many stores selling the sets to unsuspecting gentlemen. And yes, complementary works quite well. I often prefer to pick something other than the tie to complement (something in the shirt or jacket).

        Another fun thing I like to do sometimes is grab a square at random, adjust the fold as needed, and run with it.

        I greatly prefer patterned squares the vast majority of the time, as the chances of at least one color in the pattern working well is pretty good. I do have some solid ones for more “serious” pursuits and when the jacket is particularly busy.

        You’d be surprised at how often and how well this approach works.

        1. More than likely. I think unsuspecting gents think they’re getting a good deal because those sets (plus those cheap shirt-tie sets where they don’t necessarily go well together) are cheaper than buying higher quality items individually.

          As for shirts and jackets, it could potentially work. My preference for ‘referencing’ the tie sonewhere in the pocket square is because most shirts and jackets tend to be in more muted colours. Eg. Crisp white or light blue dress shirt. To me adding a pocket square gives the outfit a subtle pop of colour to contrast with the muted or subdued colours.

        2. If you think pre-packaged ties/squares are bad, Dad bought a few matching tie/suspenders packages back in his white-collar days. Paisley, no less.

          With a light blue shirt, one can wear an orange square to complement, or a red and/or yellow one for the nod towards the color triad. Or even a brown one. Many of my shirts have a little pattern to them (blue stripes, burgundy checks, etc), so it’s easy to find stuff to complement.

          Besides, with something like a solid navy tie, it doesn’t really matter what your square is (as long as it’s not solid navy, unless it is an obviously different texture). Even then, it’s pushing the boundaries of a lack of imagination.

    2. I thought the point was tie and Square in matching..i.e. identical material and pattern which IS. a faux pas imo.
      I alsothink bouteniers are for weddings and Special occasions … with a square and a boutenier one looks a bit. overthe top.

      1. I costumed a show one time where the director insisted that a boutonniere plus a pocket square was too much, but Fred Astaire wore them together, so that’s good enough for me. (Unfortunately, the director still made me change it.)

    3. I like to compare having a tie and a pocket handkerchief of the exact same material to rhyming a word with the exact same word in a poem.

      Imagine a line like that:
      “He clasps the crag with crooked hands;
      Close to the sun with crooked hands”

      Is it possible to do that? Yes. Is it the most interesting and elegant option? Usually not. Rhyming a word with a different word creates more interest and so does wearing a tie and pocket square of different material that complement each other well and each tell a story of their own.

  3. Amen to the point about too many accessories! Somebody please tell those pitiful uomos that show up in photos of Pitti Uomo coverage.

    1. Definitely. Folks that are huge fans of accessories need to follow the advice of (I believe) Coco Chanel: Look in the mirror before you leave the house and immediately take one thing off. Some guys need to take 3-4 things off. Fortunately, I’m enough of a minimalist that I never run the risk of too many. Taking off one thing would probably result in me never wearing a tie for the rest of my life.

    2. “Pitiful uomos” was funny. But even though I have no interest in dressing like that myself, I am glad that there are men dressing that way, as the sight of them answers a lot of otherwise speculative questions about possible combinations of garments. Besides that, if anyone ever calls you a “dandy,” you can always say, pointing to the Pittiful Uomini (to use the Italian plural), “No; *this* is what a dandy looks like!”

  4. I am at a stage in my career, compounded with WFH during the pandemic when I like to mix it up from time to time on video calls with a dressed up (normal) business attire. This site and the tips never fail and are always good tutorials. Thank you!

  5. I’d like to add in #3A Gym socks with a suit Usually I’m one of the first to say each to their own but to me this one really breaks an outfit. It’s bad enough with odd trouser-dress shoe combos; as an Australian Air Force Cadet when I was 12.5 to 19, I used to cringe (and think WHY) seeing cadets turn up to parades requiring ceremonial uniform with white sport socks. Apart from the Manual of Dress stipulating black or navy blue dress socks, it simply looked awful. Worse, though, was at a professional development event where a mate of mine wore a black suit to dress more professionally (compared with chinos and dress shirt at a previous one) but ruined the look by wearing little white ankle gym socks with dress shoes.

  6. I enjoy your videos. Raphael broke one of my style rules; he wore a button-down shirt with a double-breasted jacket. What are your thoughts on that?

  7. Usually to me the idea of anything but dress shoes with a suit would be a no-go. After reading this article by Antonio Centeno at RMRS, I would argue that leather DRESS sneakers (to clarify, NOT running shoes or those canvas ones like Raphael wears in the picture above) with a casual suit in some occasions looks smart and relaxed without being sloppy. Here’s the article with the images to illustrate my point: https://www.realmenrealstyle.com/best-dress-sneakers/

    In saying this, I will reiterate: this look isn’t suitable for all occasions or for all suits. It needs to be a more casual suit like the one Centeno depicts in the article. And NOT for corporate wear/professional jobs. Eg. Not appropriate for lawyers in court or business executives at a boardroom meeting. Examples of where it would be appropriate:

    – Jobs situated in places like call centres where jeans and t-shirts aren’t appropriate or one simply wants to level up their style but maintain a casual vibe

    – Casual dinner at a restaurant

    – Parties for a neat casual or smart casual dress code. Eg. The type of Christmas parties I went to in casual retail jobs. Some of the younger men wore neat jeans or dress pants with an open necked shirt but disappointingly, the majority came in jeans and a t-shirt. The casual suit and leather dress sneakers picture in the article link would’ve been a great outfit for the occasion and a step up from aforementioned jeans and t-shirt.

    1. For very casual suits in casual situations (i.e. what’s considered Smart Casual), a little leeway for something like leather “dress” sneakers is certainly worth considering, as long as you don’t go TOO far down the shoe scale. Perhaps for something like a completely unstructured linen or cotton suit? Even so, I prefer something like tan suede derbies or chukkas at the low end for the most casual suits. I’ve got an ivory/tan seersucker suit that screams for suede derbies/Oxfords in white, tan, or light gray.

  8. I appreciate your advice and tips. Here in Australia these guidelines have been largely forgotten. It is good to have a reliable ‘advice port’ to go to. Thanks.

  9. Very good and interesting article, and definitely something to take note of for the future.

    Just one thing, make sure you proof the article carefully to make sure that there are no grammar or formatting errors. In this article, I know that I have seen at least one misplaced parenthesis where it shouldn’t have been.

    1. Thank you for your kind words and for bringing this to our attention, Luqmaan! :)

Comments are closed.