21 Ways to Style Up A Boring Outfit


man trying on a checked shirt

I’ve seen this over and over again: guys have a hard time making that first step to standing out with their outfits. They have the basics down yet they’re afraid to make a mistake.

If this is you – I hear you. I was there too and I know that it’s hard to be creative with your clothes. So here’s what I’m proposing:

21 different ways to spice up a boring outfit. 21 surefire style tricks to get that girl to notice you when you pass her in the street. 21 ways to look good.

Let’s cut to the chase and start with the first one (note that the tips are in no particular order).

#1 Add a pocket square

red pocket square

A pocket square is probably the best way you can stand out by simply adding it to any outfit that incorporates a sports jacket, blazer or a vest with a front pocket.

No need to worry too much about the color: the easiest way is to match the pocket square with one of the colors on your shirt. Patterned pocket squares are okay too.

#2 Roll up your shirt’s cuffs over your sweater

This is something I’ve done a lot lately and not many guys are doing. It’s really easy to pull. You just roll over your shirt’s cuffs one length over the V-neck our roundneck that you’re wearing on top.

Make sure you first roll the sweater’s sleeves before you roll the shirt’s cuffs, though. The folding will become much easier. You’ll see how the sweater actually holds the cuff in place. The buttons can’t do that as they’re unbuttoned.

It’s easier than it sounds.

#3 Wear 1 or 2 rings

While the rising star called *preppy style* seems to ignore casual rings for the most part, this doesn’t mean you can’t wear them. Men’s rings always draw attention, especially if you move your hands when you talk.

I don’t recommend wearing more than 2 rings at a time unless you really know how to pull off that Johnny Depp look. If you want to go one step further after you’ve added the ring(s), try some other accessory, like a pendant.

#4 Roll up your pants

rolled up khakis

Rolling up pants may seem odd if you’re a new style student of mine but this is actually a hot trend. Best part: you can do this even in winter, and either show off either the top of your boots or your stylish winter socks if you’re wearing regular leather shoes.

Pant rolling is not complicated, different men roll them differently.

#5 Add a bright scarf

This should probably come very easy to you. I’m sure you already have scarves in your closet but do you have them in yellow or red?

I know it’s hard if you’re a beginner to try bold colors but a scarf is a great way to start. Remember, we assumed in the beginning that you have a boring outfit that you’d like to spice out. You’re probably wearing blacks, blues, browns or greens so why not go for a red or a yellow scarf?

#6 Add a watch

You might find wearing a watch to be superfluous since you have your cell phone with you at all times. But watches are still a style statement and wearing one will send subtle signals to everyone else that you value your time.

One thing, though. A watch can’t do much on it’s only to spice up an outfit unless it’s a colored watch. Unless you have money for a Breitling watch (which will probably kick-a$$), consider a colored watch.

Surprisingly, colored watches have made their way into men’s style so, if you think they look cool, I suggest you try them. Who knows, maybe this is just a fad that will disappear in a year or 2.

#7 Wear cufflinks

cuff links

Any accessory will spice up an outfit but few can do it as well as cufflinks. You will of course need a french cuffed shirt but it’s a great investment.

Very few men are wearing cufflinks because they can’t be attached to a regular shirt and they take longer to put on and to take off. In a world where everyone is in a hurry, take a few extra seconds to relax and put on a pair of cufflinks. You’ll feel good.

#8 Get a new haircut

man with interesting haircut

Don’t be surprised. Sometimes, a haircut is just what you need to stand out even if all you’re wearing are jeans and a t-shirt. You will, of course, need to go to a hair stylist so he or she can find you the right hair cut for you.

Us men are so scared of the idea of going to a hair salon that we’ll just use tons of gel to mold our hair into what we think looks cool. Most of the times, it ends up looking worse that if we had left it alone.

#9 Wear your scarf in your jacket’s pocket

If it’s too hot to wear your scarf around your neck, an alternative is to just stuff half of it into one of your jacket’s pockets. The other half will hang and, if the scarf is in a bold color, it will draw the eye in that direction.

You need to carefully fold it before you put it in your pocket so that it fits as much of the pocket’s space as possible (and to avoid creating a bump).

Careful so that it doesn’t hang too low, though.

#10 Wear a classic umbrella

I know we’re all used to seeing those compact umbrellas which are very practical. They’re easy to hold and they fit well into any bag. Who wouldn’t want one?

A stylish man, that’s who. A classic umbrella is something you’ll see very rarely on the streets these days. If you’re just going for a walk in the park try one and you won’t be disappointed.

#11 Try no-show socks

No show socks actually create the illusion that you’re not wearing any. This is the best way to get that sockless look that so many men have adopted over the past few years. The outfit might still look dull… up to the point the eyes fall down to your feet.

#12 Get an outstanding pair of shoes

double monk strap brown shoes

photo: leffot.com

Here’s a revelation that I had a while back: shoes that are stylish and that stand out on their own cost just as much as those square-toed, thick-soled boring shoes.

I bought a pair of shoes that actually have 3 colors on them: green, camel and dark brown. You have no idea how much attention they get on the street.

Now, if you’re wearing a simple outfit, such shoes will stand out even more. I wrote a few times about some amazing shoes that you can find in stores (though it won’t be easy).

#13 Wear a hat

It’s amazing what a hat can do to even the most boring of outfits, in addition to instantly adding inches to your height. If you’re clueless about hats, go for a fedora as it will suit most head sizes and most outfits.

#14 Colored socks

While it’s easy to go overboard with these if your outfits stand out, a pair of colored socks will bring a breath of fresh air to your generic attire.

If you’re wearing blacks, blues and grays, I would advise you to a pair of striped red socks with grey or black stripes. This way the red will stand out but the grey or black will temper it.

#15 Wear a sports jacket with your shorts

This won’t work with any type of shorts, only with those stylish cotton ones. Don’t try this with the shorts you’re wearing at the gym.

All you have to do is wear a sports jacket or a blazer with an outfit that already has the aforementioned shorts. This will get you a lot of attention from the ladies but don’t worry – sports jackets are one of the manliest items of clothing out there so there’s no chance that you’ll be ridiculed by other guys. Have I ever given you wrong advice?

#16 Wear an ascot tie

Think of an ascot tie as something between a tie and a scarf. It has a little from both worlds and it’s really classy. As long as you’re wearing a dress shirt, you can just throw an ascot to the mix.

#17 Wear a circular scarf

I know that one of the tips was to wear a scarf but this one is a little different. A circular scarf is one that has the two ends sewed together so the only way to wear it is to put your head through the loop.

I usually make 2 loops and put my head through both of them. The end result is that it adds a little more volume to from the chest up, which is a very interesting effect.

#18 Wear an interesting pair of sunglasses

No, I’m not talking about those sunglasses that look like you’re going snowboarding. There are more stylish alternatives. Some have colored lens, other have colored frames.

If you just add such a pair to any dull outfit, it will instantly awaken it to life. Plus, it will bring a lot of attention to your face (which is where you want people to look anyway).

#19 Try an ascot cap

Throwing an ascot cap over an outfit is very easy but you should be a little careful on how you match it.

If your outfit is based primarily on black, a black or a grey ascot cap is ideal. If it’s based on brown, a brown, khaki, tan or beige cap is best.

#20 Wear a coat in a lighter color

If you have a generic winter outfit, there’s no better way to stand out than to wear a coat in a color such as camel, dark red or light gray. The contrast with the underlying clothes will be perfect. I know I’m asking you to wear a lot of color this time but it won’t hurt to just try a few on at the mall and see how you look like. Pretty please.

#21 How about a tie clip?

tie clip

Well, this is my last of the 21 ways to spice up a boring outfit and I didn’t say anything about ties!

I think ties are starting to get too common so, instead, I’m going to suggest that you take things one step further: wear a tie clip with your tie.

Initially designed to keep ties from moving around when you walk (or because of the wind), tie bars and tie clips make a great fashion statement.

Just make sure you place the tie a little higher from the middle of the tie (at about the same level of the 3rd shirt button). The second thing to keep in mind is that the clip should never be wider than the tie width at the point of attachment. Easy.

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4 Comments

  1. Michael Clear
    May 7, 2012

    I have lately been using a nice pen as a tie clip. If you have the right pen its a cool look and keeps your pen handy for quick use on the job.

  2. Raul
    May 19, 2012

    i Have a black and gray vest but I dont know what to wear wwith it and i want to used it for a wedding.?

  3. May 19, 2012

    Michael Clear :

    I have lately been using a nice pen as a tie clip. If you have the right pen its a cool look and keeps your pen handy for quick use on the job.

    Wow, I’d really like to see how that looks. Do you have a photo?

  4. May 19, 2012

    Raul :

    i Have a black and gray vest but I dont know what to wear wwith it and i want to used it for a wedding.?

    Is it a waist coat (with buttons)? If so, you can just wear it with a pair of black/gray pants, a pair of black shoes, a black belt and a light-colored shirt (white, light blue, blue).

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