10 Sneaky, Easy, and Cheap Ways to Dress Up

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Dressing up doesn’t always mean dressing to the nines. Being subtle about it, especially in our ever-increasingly casual culture, is often the way to go. And it’s also cheaper this way! Here are 10 ways to work a little style in on the sly, while also staying on budget.


#1. Wear a simple dress watch with everything

Timex watch

Even with a t-shirt and jeans. Good enough for your James Dean, Cary Grant, and your Grandpa, good enough for you. Yes we love some wrist-chunk around these parts, but wearing a slim and simple dress watch both dressed up AND down looks weirdly classy. There’s a real high-low thing going on, even if the price of the dressy watch was anything but high. Most of us have a dress watch already, but it just doesn’t see as much use these days. Here’s reason to dust it off and put it to use once again.


#2. Put in a pocket square

guy in suit with pocket square

Having a bit of pocket square sticking out from a suit, blazer, or sportcoat’s breast pocket is one of the easiest things you can do to level up a basic tailored look. Especially if you’re skipping the tie, and going with a solid/quiet color of suit. Also works if you’re doing the jeans + blazer thing.


#3. Wear some patterned socks

Patterned Socks

You don’t have to get mega crazy and wear hyper contrasting bold stripes. No one is recommending a Wicked Witch of the East look. Subtle dots or thin stripes will do the trick. And if you wanna wear shark socks? So be it. More power to you us.


#4. Try a shawl collar sweater instead of a hoodie.

guy in shawl collar sweater

There are many, many alternatives to wearing a hoodie. And no one is saying you need to trash your hooded sweatshirts. But keeping them in the drawer every once in a while in favor of a timeless shawl-collar can help up your style-quotient a touch.


#5. Shave clean, or trim your beard.

man shaving with straight razor

Many of us go a long, lonnnnng time between beard trims, scruff cuts, or clean shaves. But a clean shave or just getting consistent with keeping your beard length in line can make an enormous difference. Just be aware that even a simple trim or shaving after a bit of stubble can leave you feeling weirdly unfamiliar with your very own face.


#6. Embrace the Chinos Chukkas & Polo look

chinos chukkas polo

Intentional enough to look dressed up, yet still nowhere near suit and tie. Here’s more on why it works, and here’s our archive of many, many ways to pull this combo off.


#7. Clean your place

simple green

Your home is a reflection of your own personal style. So picking up, dusting, vacuuming, and cleaning bathrooms absolutely counts towards “dressing up” and feeling your best.


#8. Put on a knit tie

man wearing a knit tie

Knit ties are inherently more casual than their smooth silk counterparts. The texture, colors, and often matte finish makes these things lean friendly, and much less I’m here to lay-off 30% of your workforce. You can usually get away with wearing one of these even in a super casual work environment. Just don’t do it often. You’ll alienate your co-workers.


#9. Wear your brown dress shoes with dark wash jeans

brown dress shoes

  1. Allen Edmonds Park Avenue – $395 (shown above = weatherproof brown, all but sold out)
  2. Allen Edmonds 5th Ave. in Mahogany – $299 ($395)
  3. Charles Tyrwhitt Cap Toes in Dark Chocolate – $249
  4. Bruno Magli Luna Oxford – $189.97 ($395)
  5. Nordstrom Dane Cap Toe Oxford – $99.95

As long as they’re a conservative shape and not too pointy, you should be able to wear your go-to brown dress shoes with dark wash denim. Those are Park Avenues in the dark brown “weatherproof” leather shown above, but the mahogany is a perfect shade here too. And yes, I hiked my pants up a touch to show off the socks for the camera.


#10. Wear chinos instead of shorts when it gets warm

man spraying himself with hose

Make sure they’re a washed, more casual fabric. Or if they’re tech, something matte and easy wearing. You don’t want pressed and slick office-ready trousers. Wear them with classic court style sneakers, and if you still feel a little funny wearing chinos instead of shorts, try cuffing the hems a touch for a more casual look.

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