60 Simple Outfit Upgrades For Men – Winter 2019 Edition

Revtown Jeans

Call it a blessing, call it a curse, but I know this much about myself: I’m an over-thinker by nature. I take pride in going above and beyond. I’ve been called “extra” by friends, family, and co-workers more than once and, occasionally, that gets me in trouble.

When that happens, I’m reminded of a lesson my dad constantly preached in our house growing up, applying it to every tedious, procedural task, from yard work to algebra homework: “Keep it simple, stupid.”

In the words of my father, consider the KISS system. Don’t overthink it. Keep it simple, stupid.

It’s so easy to be extra and add layers to complexity to almost everything in life. But that’s how you get yourself in trouble, becoming a victim of your own perceived ingenuity: Experimenting with too many contrasting flavors in the kitchen can turn an nourishing homemade meal into a bland, unpalatable chore, destine for the waste basket. Mix all the colors together into the same paint can and everything just turns out gray.

The same goes for curating a personal aesthetic. Flash too hard with a neon tie or a bulky, cumbersome watch and you’ll come across like a clown, unless you have the confidence to truly own being that clown. Rather, just keep it simple, stupid. Simple outfits for men often come effortlessly, with cool upgrades to your look gradually procured over time. The swagger that comes from putting together a cool outfit is a marathon, not a sprint.

Think about putting together outfits for a personal style it like you would putting together furniture: Step-by-step, feeling more and more complete with each new item of clothing or accessory added to your wardrobe over time. Yes, it’s a chore at first. But after buying a great pair of premium jeans that you love or a watch that makes your work outfit pop, you’ll feel a sense of accomplishment. As a man, it’s not hard to build a closet of simple and easy outfits, as long as it’s understood that you should be buying something you love to wear.

The shoes, watch, shirt, or suit don’t make the man. The man makes the man. But a couple simple style upgrades can nudge a man in the right direction when it comes to confidence.

Without further adieu, our specific men’s style tips: Here are 21 easy men’s outfit upgrades on what to buy to make your ‘fit stand out from the pack. These are timeless favorites from some of the best menswear brands out there, all aspiring for the same thing – For a man to look his very best so he can be at his best.

Revtown Jeans


[1] Revtown Automatic Denim Jeans [$75]

[2] Revtown Khaki Jean [$75]

Revtown Jeans

[3] Flint and Tinder Mill Pant [$98]

[4] Proof Rover Pant [$98]

[5] Dockers Workday Khaki Flex Pants [$29.99]

[6] Proof Nomad Pant [$98]

[7] Taylor Stitch The Camp Short [$102]

[8] Flint and Tinder 365 Pant – Slim [$98]

[9] Revtown Sharp Denim Jeans [$75]

Revtown Jeans




[10] Challenger Pullover Hoodie [$17.97]

[11] The Faherty Stretch Seaview Shirt [$168]

[12] Goodthreads Men’s Slim-fit Long-Sleeve Solid Oxford Shirt [$25]

[13] Wrangler Authentics Men’s Long Sleeve Plaid Fleece Shirt [$19.99]

[14] The Filson Vintage Flannel Work Shirt [$145]

[15] Criquet Long Sleeve Players Shirt – Peacoat [$105]

[16] Patagonia Fjord Flannel Shirt [$89]

[17] Jockey Staycool+ Crew Plain Black Neck T-Shirt [$25]

[18] Mollusk Stripe Hemp Crew [$123]

[19] Taylor Stich The Everyday Blazer  [$398]

[20] Revtown Airspun Henley [$40]




[21] Fossil Commuter Hybrid Smartwatch + Fitness Tracker [$175] 

[22] TUDOR Black Bay Swiss Dive Watch [$2900]

[23] The Zodiac Super Sea Wolf [$1395]


[24] Official Hawaii Lifeguard Association Dive Watch [$250]

[25] Vincero Rouge [$229]

[26] DuFrane WAtches Barton Springs 656 Diver [$599]

[27] The Fossil Chase Timer with Whiskey Leather Band [$145]





[28] PF Sandlot Center Hi [$60]

[29] Rancourt & Co. Wolf Boot [$395]

[30] adidas Stan Smiths [$76]

[31] Lems Boulder Boot [$106]

[32] Sperry Boat Shoes [$59]

[33] New Balance X90 Knit  [$110]

[34] Red Wing Leather Chukka Boot [$179]

[35] adidas Ultra Boost [$180]

[36] Nike x Carhartt WIP Air Force Ones  [$130]

[37] PF Flyers Made In The USA Center Hi [$160]



Warm Threads

[38] Patagonia Down Sweater Vest [$111]

[39] Criquet Sweater Fleece Jacket [$165]

[40] Howler Brothers Rounder Vest [$135]

[41] Patagonia Stretch Rainshadow Jacket [$199]

[42] Faherty Pacific Poncho [$94]

[43] Obermeyer Carson Down Vest [$129]

[44] Free Fly Bamboo Lightweight Hoody [$55]

[45] Peregrine Waxed Bexley Jacket [$299]

[46] The Touch Me Tribal Vintage Fleece Hoodie [$49]

[47] Flint and Tinder 10-Year Hoodie [$98]

[48] Brixton Roping Jacket [$139]

[49] Proof Nova Series Insulated Jacket in Olive [$198]

[50] The Brixton Suds Hoodie [$69]



[51] Arnette Hang Five Glasses [$89]

[52] Patagonia Fisherman’s Rolled Beanie [$29]

[53] Yellowstone Short Cuff Gloves [$165]

[54] Cremo Beard Care Products Combo [Starting at $9.82]

[55] Patagonia Can’t Eat Money Trucker Hat [$24]

[56] Carhartt Men’s Rexburg Hat [$19.99]

[57] Relwen Packlight Shell [$117]

[58] Filson Ranger Backpack [$225]

[59] Arcade Belt Co. YOSAR Hudson Belt [$32]

[60] Sock Fancy [Starting at $11 a month]

Sock Fancy


Follow BroBible publisher Brandon Wenerd on Twitter. 

Presented with support from the following brands: Fossil Watches, Revtown Jeans, and Huckberry

The BroBible team writes about gear that we think you want. Occasionally, we write about items that are a part of one of our affiliate partnerships and we will get a percentage of the revenue from sales.