How to dress up without REALLY dressing up – 12 Tips

It’s a weird time, isn’t it? People are getting back out there (obligatory acknowledgement that recent news has been up and down), and we’re starting to dress up again. Yet when it comes to dressing “nice”, too much too fast can leave you looking like you’re trying to show everyone up. Here are 12 tips for looking a little more put together without looking overdressed. For those who want to start looking a little more 2022, and a little less 2020.

 

#1. Put on an unstructured, casual sportcoat over a t-shirt or polo

• Wallace & Barnes Cotton/Linen Chore Blazer – $119.99 FINAL ($150)
• Old Navy Built-In Flex Blazer for Men – $60ish
• Suitsupply Stretch Cotton Lazio Fit Jacket – $259
• Banana Republic Supima Cotton Sweater Blazer – $149
• Bonobos Unconstructed Italian Wool Hopsack Sportcoat – $400
• J. Crew Italian Wool Knit Blazer – $309.50 ($450) shown very top of post

You don’t even have to tuck anything in! No one is saying you have to wear some stiff, starched dress shirt. And no one is saying these sportcoats are stiff, hard shouldered, yacht-club style blazers. Instead, there are plenty of sportcoats out there right now made in more casual fabrics and with less structure. They wear easy, look great, and go exceptionally well with t-shirts, polos, and yes, even the rare button up, tucked in shirt.

 

#2. Wear a watch

• Casio Men’s Dive Watch in Black or Blue – $50ish review here
• Invicta Pro Automatic – $80ish
• Orient Bambino V3 “Bauhaus” Automatic – $110 to $120
• Nodus Retrospect III – $475
• Lorier Gemini Mechanical Chronograph Watch – $499
• Hamilton Murph Automatic – $995

Try it. It works. A watch can be the difference between “I got dressed” and “I just rolled out of bed.” Somehow, someway, a wristwatch can make even the most casual outfits look a bit more complete. Maybe it shows that you weren’t in a total rush to get out the door, and/or it shows that you might have to be somewhere, at some point, so your day isn’t one big humming static haze of directionless ennui. Even if your day IS one big humming static haze of directionless ennui. ESPECIALLY IF YOUR DAY IS oh forget it.

 

#3. Wear casual chinos instead of shorts (with your tees and polos)

• Banana Republic Core Temp Chinos – $60ish
• Bonobos Stretch Washed Chinos – $99
• GAP Khakis – $35ish
• Target Goodfellow Slim Fit Chinos – $22.99
• Lululemon Warpstreme Commission Pants – $128

If once you get the chinos on it feels… weird? Like you’re still a little dressed up? Here’s a trick: cuff your pant legs. Not like super stacked four folds or anything. Just turn up the bottoms. Makes them look (and feel) much more casual.

 

#4. Button the top button of your polo

Simple tweak. Big visual difference. Not saying you have to do it all the time. Hardly. But buttoning the top button of your polo makes things look just that much more cleaned up. Symmetrical. Dialed in. Mod-ish, without looking foppish. See the movie Tenet for why this looks all kinds of great.

 

#5. Choose Twill over Terry or Fleece when it comes to joggers

• Banana Republic Organic Traveler Jogger – $60ish
• Marine Layer Slim Fit Saturday Jogger – $71.98 ($110)
• Goodthreads Slim-Fit Washed Chino Drawstring Pant – $30
• Abercrombie All Day Utilty Joggers in Olive Green – shown above & sold out, but these may be close?

You want crisp. Not squish. Joggers aren’t going anywhere. But if you’re gonna wear joggers and you DON’T want to look like you just peeled yourself off the couch, then leave the terry/sweats-style fabric at home. Go with joggers made out of a twill fabric. Something that looks like it was once a pair of real pants before they slapped an elastic waist (and possibly cuffs) on it.

 

#6. Get on board the short sleeve button up trend

• Bonobos Riviera Short Sleeve Button Ups – $79
• J. Crew Factory Short-sleeve flex washed casual shirt – $35ish
• Banana Republic Slim-Fit Tech-Stretch Cotton Shirt – $50ish
• Goodthreads Standard-Fit Short-Sleeve Printed Poplin Shirt – $25

The cuts, fabrics, and patterns make these look like anything but the short sleeve dress shirts you see on someone going door to door preaching their chosen faith. A style upgrade over a t-shirt, but still anything but stuffy.

 

#7. Wear Stripes

• J. Crew Slub jersey T-shirt in deck stripe – $36.50
• Amazon Goodthreads Men’s Short-Sleeve Indigo Crewneck Pocket T-Shirt – $25
• Target Goodfellow Striped T-Shirt – $9.99
• J. Crew Linen-cotton sweater in stripe – $39.99 FINAL ($79.50)
• Lululemon Evolution Short Sleeve Polo Shirt in Stripe – $88

Stripes are immensely versatile.  Thick rugby style stripes, classic Breton style stripes, or thin micro stripes. On tees, polos, henleys, sweats, etc. More intentional than something solid, but still casual.

 

#8. Learn to love the suede chukka

• Made in the UK Sanders Suede Hi Top “Playboy” Chukka Boots – $250ish (review here.)
• Clarks Men’s Bushacre 3 Chukka Boot – $85 ($110)
• Jack Erwin Reade City Chukka – $165
• Made in Italy Astorflex Desert Boots – $175

They’re the original high-tops. Made for comfort, utility, and to be worn with just about everything. From washed jeans and a sportcoat (shown at the top of this post), to beat up chinos and a t-shirt.

 

#9. Embrace the laceless. Work in suede chelseas (boots and sneakers)

• Made in Italy Astorflex Chesleas Sneakers – $119.98 ($185)
• Allen Edmonds Nomad Suede Chelsea Boot – $249.97 ($375)
• Made in Italy Astorflex Chelseas – $195
• Banana Republic Tully Sneaker Chelsea – sold out/shown above
• SeaVees Coronado Sneaker Chelseas – $103.98 ($160)

Chelseas are great at dressing down more tailored wear like trousers, dress shirts, and suits or blazers. Chelsea sneakers dress UP more dressed down stuff like washed chinos and pocket tees. And I know this for certain: You are more likely to wear good looking shoes (casual or dressed up) when you don’t have to tie them. I know that sounds insane. Weird as it may seem, lacing up a sleek pair of dress shoes might seem a little… “heavy” when the world is currently slopping around in sneakers. So if you want to wear something sleeker, stick to chelseas.

 

#10. Favor tech-wear that DOESN’T look like workout gear

• Lululemon Warpstreme Commission Pants – $128
• Banana Republic Aiden Slim Fit Core Temp Chino – $50ish ($98)
• Rhone Delta Pique Hidden Button Down Collar Polo – $88 (or $66 when you buy 3)
• Old Navy Slim Go-Dry Shade StretchTech Shorts for Men – $30
• J. Crew Tech Short in 9″ or 10.5″ inseam – $24.99 FINAL w/ SALEONSALE ($69.50)
• Abercrombie & Fitch Airknit Curved Hem Crew Tee – $15 ($25)
• Target All in Motion Performance Tee – $12

I grew up in a place (upper midwest) where once it hits 45 degrees, every dude big and small starts walking around wearing baggy basketball shorts, sneakers, and an oversized gym t-shirt. “But it’s comfortable” they’d say. Well guess what? We now live in an age where you can wear good looking pants, shirts, polos, tees, and more, all made out of the same sweat wicking, super breathable materials that your gym gear is made out of. All without looking like you were teleported out of your weekly pickup game at the Y!

 

#11 Wear a suit, but skip the tie in favor of a pocket square with some color

• Kent Wang Patterned Pocket Squares – $45
• The Tie Bar Border Pocket Squares – $10
• The Tie Bar Liberty Print Pocket Squares – $10
• The Tie Bar Gingham Pocket Squares – $5 ($10)

Get more use out of your suits. Wear them. Especially when you don’t have to. Dressing down a suit isn’t that hard. Skip the necktie, and instead favor a pocket square with a little color and/or pattern to balance out your look. It works. Promise.

 

#12. Get your casual fits right. Room to move, but not baggy.

The same old rule applies: Clothes should skim. Not cling. Not billow. You absolutely have to be able to easily move around in your clothes. They shouldn’t restrict. But they also shouldn’t drag through the air as you move either. You’ll know it when you see it, but more importantly, you’ll know it when you feel it.