5 Quick Style Wins for Men

I love a quick win. It helps build momentum. Once I get a few wins and see something working, the rest starts to fall into place.

For a lot of guys who talk to me about improving their style and wardrobe, they’re simply overwhelmed. There’s so much when it comes to choosing the right items, quantities, colors, fits, fabrics, and brands.

Instead of trying to tackle it all, it helps to simply get a few quick wins under your belt. These can quickly elevate how you look and put you on the right path to improvement.

Let’s dive into five quick wins you can use right now.

01 | TAKE A TRIP TO THE NEAREST TAILOR

After working with 1200+ guys, I can tell you that every one of them would have benefited from having some of their clothing tailored.

You probably already have a few items in mind that could use a bit of an adjustment. If there are a few items you love but you know they don’t fit you as well as they could, start there.
I’ve found that for most guys, 20-30% of their wardrobe usually needs to be tailored. If you’ve got more nuanced issues with sizing, such as being taller, shorter, more muscular, etc., expect that number to go up. I'd guess tailor close to 40% of my items.

The best thing about tailoring is that you don’t have to be exactly sure how it’s supposed to fit - you just need to know that something is off. A tailor can help you work through what that is. If it can’t be altered, they’ll let you know. But you can tailor a surprising number of things.

Almost all the alterations I see a client needs when I’m working with them in our personal styling service are either shortening pants and shorts to a better length or taking in the sides of tops so they don’t look so boxy. You’ll likely be doing the same to most of your items.
Get a small pile of items together and head to the closest tailor to you. You don’t need the best right now. Your alterations are likely very simple. You need someone close by so you’ll actually use them.

02 | GET RID OF COMPLICATION

Most men think they need to add more. More patterns, colors, items, etc.,

This mostly creates complexity and mental strain when you’re trying to get ready.

Think about it like this: When you’re learning to cook, do you want to try a recipe with 50 ingredients and pages worth of instructions? Instead, you’d be better off starting with a dish made from simple ingredients and clear, easy-to-follow instructions.

Walk before you run. Most guys' style issues stem from trying to do too much. Simplify. You do this in two ways:

First, simplify your closet. There’s stuff in there you haven’t worn and will never wear. Your mind is trying to look at all the available pieces to put together an outfit, and it’s burning out trying to figure out what actually works and what doesn’t. We need to free up mental space.

Pull the weeds.

Once you do, you’ll have an easier time creating outfits because you’re only left with good ingredients. I promise you this is a much more important step than purchasing new clothing right now.

Second, simplify your outfits. Less is truly more here. You don’t need more color. Everything doesn’t have to have a pattern on it. You can wear something without logos or graphics.

The more you simplify your items, the easier it is to pair things. When you add color, pattern, etc., you now have more elements to consider when pairing. It’s like the more ingredients you add to a dish, the more you have to worry about them all blending well together.

Stop and simplify. Use neutral colors and solid items, and you’ll see how much easier it is to pair things together.

If you want to add some spice to your outfit, you can always:

03 | ADD A THIRD PIECE

Layers. You need them.

This is one of the easiest ways to elevate an outfit. Instead of adding more color, pattern, etc., just add a layer. This can be anything you put over the top of another item.

Start with something like a plain white tee, then add an overshirt or jacket.

This adds depth and dimension to the outfit, spicing up something that may otherwise be considered boring.
I find that a lot of the clients I work with just don’t have many options here, so if that’s you, it’s one of the first pieces I would think about adding in when you…

04 | SHOP FOR ONLY 5 PIECES

Yes, only five.

Most of your issues with shopping come from the overwhelm of not knowing where to go or what to buy. You feel like you need to rebuild a huge chunk of your wardrobe when you go out shopping, and you feel pressure to make purchases, even if you probably shouldn’t.

The goal is not to leave with the most clothing; the goal is to leave with the most useful clothing.

5 items can change a lot. A fun layering piece, a good pair of shoes, a better-fitting pair of trousers, etc., and you’ve not only got a good outfit, but you’ve got pieces that can elevate all of your existing outfits.

You may have a sense of what you need already. If you don’t, you can use this wardrobe guide I’ve developed to help get you started. It’s free.

05 | DON'T BE LAZY

A quick reminder that a lot of this is effort-related.

I live in San Diego, one of the worst dress places in the country, where flip-flops are acceptable (and often encouraged) for every occasion.

When you’re surrounded by casual attire and guys who don’t care, it’s easy to slip. Most guys don’t actually give a damn. Don’t let that be you. It’s your strategic advantage.

Because of most men's complacency, you’ve got an edge. If you even attempt to put together something smart, you’ll do better than most. It’s never been easier. Don’t let that opportunity go to waste.

So next time you’re putting together an outfit, apply yourself a little. Wear something more elevated than you might normally choose. Think about how to pair something differently than you normally do. Just think about it. Even 30 seconds of effort can yield you a better-looking outfit.


Quick wins are helpful. They give you a good place to work from.

Style itself is a quick win. There is no better way to instantly increase your attractiveness, status, and self-confidence than by putting on clothes that look good on you.

So building out your wardrobe and improving your style is something you should take seriously.

And if you want help with it all, you can work with me to do it.

You’ll have me and my team 1-on-1, personally build your wardrobe and style you so you never have to worry about shopping or putting together the right outfits.

It's what all this was all designed for - we've taken over 1200 guys through this personal styling process, getting them looking and feeling their best.

You can schedule a complimentary call with me here, and I’ll give you the details.

Hope this helps.

Patrick