Style

28 Style Tips for Guys

Big ideas and small changes for 2019

Happy Reboot Month!

Today, Taylor talks style upgrade tips…

My mom worked in the fashion industry through most of my childhood. Naturally, my style education started very young. I wore clusters of eclectic pins on the pocket of my (tiny) denim jacket because she did. I wore pink cowboy boots through most of preschool because she had black ones. Today, I wear those same black cowboy boots almost daily when I go to visit my parents in Idaho.

It’s a lucky break, being the beneficiary of my mom’s great taste and personal style. At this point, I hardly know what I’ve cultivated on my own and what’s seeped into my bloodstream through her. Her jewelry adorns my wrists and fingers. Her mom’s coats sit in my closet. The throw pillows on my couch used to reside in our house in Seattle.

Because our style is so intertwined, the moments when I find something that feels truly mine always stand out.

A few years ago, I purchased a camel-colored wool coat from Club Monaco. It was a pivotal moment for me, and for my wardrobe.  As I was swanning around the dressing rooms, absolutely delighted with myself and how f*cking great I looked in this coat, I remembered something I’d overheard my mom say to a friend a few years ago. It went something like, “Coats and jackets are the one thing, other than shoes, that can completely transform an outfit. Anything you wear looks more polished and stylish with a really good coat over it. That’s why I never feel bad about how many I have!”

A style pivot

This moment marked a pivot for my style. The stuff that used to be hers was always “the best” I had. Now I had this gorgeous, classic, transformative coat that I had purchased all on my own, but could still track her influence as part of why I knew it would be a worthy investment.

This little anecdote illustrates why my “style advice” always includes a gentle push towards outerwear. It’s a key element of my wardrobe that makes me feel like an absolute boss, and a nugget that’s as useful to men as it is to women.

I’ve spent the last couple weeks asking friends, industry experts, and my Instagram community to share their style tips. As part of Reboot Month here on SG, we wanted to share as much knowledge and inspiration as we could gather.

As you’ll see, that knowledge really runs the gamut. There are big picture ideas about confidence and self-assurance, and ultra-specific tips on replacing buttons or tailoring a vintage find. That’s the nature of personal style and how evolves and improves; changing your mindset translates to little actions that all come together to make you look and feel like the best version of yourself.

6 Big Ideas & 28 Amazing Tips For Improving  Your Style

1. Start with the basics.

“Start small, focusing on building blocks for a great wardrobe that fit within their lifestyle. So, if you work in a more casual office and find your need to still wear a nice collared shirt, focus on finding the best possible version of that shirt in terms of fit and fabric. From there, focus on one great pair of jeans that you love, for instance. So, the idea of “seeing the forest for the trees,” if you will. Before you know, you’ll have a wardrobe stocked with basic pieces that … really aren’t so basic.”

Beau Hayhoe, The Style Guide

 

“With a million brands—and their last minute, wild online sales—you should always have your measurements ready so you don’t debate the hundred different sizing specs while shopping.  Next time you are are dropping off clothes at your dry cleaner, see if they do alterations (most do), and, if you ask nicely, they will have no issue spending 5 minutes to measure you. Jot each measurement down in a Note on your phone and then have it to compare to apparel measurements and retailer size charts every time going forward.”

Joseph, 31, New York NY

 

“Figuring out that size and fit are two different things made all the difference for me.”

Ben Conway, via Instagram

 

“Don’t buy anything you don’t love. Otherwise you won’t wear it, and you’ll actually end up with a closet full of clothes and nothing to wear.”

Demetri, 33, Seattle WA

 

“The biggest leaps for me (outside of following SG, seriously!) was to simply talk to people about their style and where they shopped. I have colleagues and friends who have great style and I almost view it like networking but with clothes. It’s helped me grow my understanding of brands and shops and that’s lead to an awesome selection of clothes in my closet.

Jerry, 33, New York NY

2. Shop, edit & update.

“Find what is comfortable for you—and then buy it in multiples.”

Elana Hasin, via Instagram

“The one really quick, easy and inexpensive way to make a huge impact in your entire wardrobe is to change out the buttons. Besides tailoring a look to make sure it fits properly, if you replace the cheap plastic buttons on your clothing with horn or a higher quality fastener it will instantly elevate your fast fashion into a more luxurious look.”

Jeanne Yang, Celebrity & Editorial Stylist

 

“Try on a size smaller than usual because one, you may surprise yourself with the fit, and two, Especially with leather jackets and denim (jackets & jeans), they’ll mold with you over time.”

Joseph, 31, San Francisco, CA

 

“Throw out the things you’ve had and worn a LOT. Replace them with the exact same thing if you need to.”

Lisa Bowman, via Instagram

 

“Everything in your closet you should love and wear. I get aggressive with cleaning out closets (even my own!), especially to start the New Year off right. For example, for a recent client I removed 55% of his wardrobe that didn’t fit or was just old. That was eight huge bags full of clothing!”

Cassandra Campa, Personal Stylist

“Watch Marie Kondo [Tidying Up with Marie Kondo, on Netflix] and find clothes that “spark joy” for you.”

@bonobian, via Instagram

 

“Learn how to sew and buy a sewing machine. Trousers are very easy to hem and surprisingly easy to taper. I’ve even shortened short sleeves myself because the cuff is only held in place with one seam. The second, parallel seam is not used for attachment.”

@Jammysod, via Twitter

3. Consider colors, prints and patterns.

“If you have a wardrobe filled with what I call “menswear neutrals”—black, grey, white, khaki, brown, light blue, navy, olive—you can’t go wrong with color. These colors look great together, and with pretty much every other color out there. Just make sure your outfit consists of these colors, and you’re good to go. And if you ever wanted to try a color that isn’t a menswear neutral, you can easily wear it (since you know menswear neutrals go with everything) and know it matches well.”

Baron Cuadro, The Effortless Gent

 

“Some advice I heard one time that has always stuck with me, aim on having just one part of your look do the “talking”. Whether that be mixing a bold print suit in with a textured solid tie and crisp white shirt, or going full tonal but adding in a cool statement jacket or shoe. Decide what part of your look you want people to notice most. I’ve always felt that was a good rule of thumb to follow when wanting to stand out for the right reasons.”

Michael Corrigan, Publicist for The Tie Bar

 

“Find your shade of yellow and wear it. Everyone will be impressed.”

Gabi Meyers, Queen of 5 Days 5 Ways

“Color is your friend. Learning to wear stuff that’s not black makes people want to be around you.”

Scott Young, via Instagram

 

“This weekend I was at a ‘black tie optional’ wedding in the Smokey Mountains of Tennessee. There were a ton of musicians there with personal style coming out their ears. Literally, one guy was wearing a piece of string looped through his earlobe like an earring.) And while the cowboy hats, John Lennon sunglasses and bolo ties were certainly noteworthy—my favorite style moment came from a friend’s boyfriend, just a normal, sweet guy from Seattle, who was wearing a rented tux. But it wasn’t just any ol’ tux.

His girlfriend convinced him to try a black-and-white gingham jacket with classic tuxedo pants—and you should have see his smile! His swagger! I told him how much I loved the jacket, and he told me he’d never worn anything like it in his life, but he’d never received more compliments in his life, either. His eyes had been totally opened to a whole new (and playful) side of his taste he never even knew was there.”

Taylor, 33, Your Favorite SG Contributor (lol)

 

“I’ve built up a big collection of colorful and patterned novelty socks that I especially like to wear in the winter. In Maine with bad weather, you often take your shoes and boots off at people’s homes, so ratty socks with holes won’t do. My fun socks make me feel like I’m still fully dressed, plus they’re usually a good conversation-starter, too.”

Luc, 35, Portland ME

4. Try something new… And maybe something old.

“Finding Todd Snyder and Billy Reid changed everything for me and my style.  A quality and timeless design that will last me a lifetime.”

Jeff, 34, Columbus OH

“Try upping your suit game with a vintage original. I found a wonderful grey Yves St Laurent suit at an estate sale. Originally I bought it just as a potential suit to wear to costume parties—the intention was not that it would become an essential part of my dress wardrobe. Anyway, the suit was squarely from the Mad Men era, and I could tell it was high quality, but I found it hanging next to ratty other suits at an estate sale. It had missing and chipped buttons. It was $15 for the jacket and matching pants. The pants were slightly flared but actually looked flattering when I first put on the suit. It needed some good TLC from a tailor, so I spent approximately $150 to have the it altered (small adjustments to sizing) and to replace the buttons (with advice for selection coming from the tailor). I’ve now worn the suit dozens of times , all year long, and always get compliments.”

Jason, 34, San Francisco

 

“Be brave and take the chance on something you think you’re not cool enough to wear!”

Megan Kernan, via Instagram

5. Having  easy, go-to wardrobe pieces can make all the difference.

“A few years ago I started dressing in a manner that allowed me to effectively wear the same outfit to 80% of life. Dark blue but not navy trousers paired with Rancourt penny loafers (with natural color with rubber outsoles added) and a combination of white and blue button down and spread collar shirts from Kamakura and LL Bean. Nothing very precious. You can go on a hike, play golf, go to your club without being rejected for jeans, and throw on a blazer or sport coat and attend any meeting in the city. All in the same outfit. Compared to 90% of people you are “dressed up” but with the right materials you can pretty much do anything and go anywhere. This also aids and simplifies travel, as the number of “outfits” required is vastly reduced. Depending on the weather you can switch between heavier oxford cloth for chilly and intermediate weather and lighter pinpoint or more dressy finely woven shirts that do better in the heat. For warm trips I take a cotton sweater and a tropical weight blazer. For cold trips, a lightweight wool v neck and a regular weight blazer.”

Duncan, 32, Greenwich CT

 

“When it comes to first dates, a man’s style is hugely important. You want to walk the line between looking like you tried, and looking like you tried too hard. So, if one of our clients asks for help improving his first date look and doesn’t want to buy new clothes, my golden rule is: whatever fits best *is* best! Even if it’s not the trendiest item in your closet, your date will definitely notice the dapper, pulled-together look of sleeves and pants that hit just right. Jeans are the only pants I recommend for dates—then he can add a well-fitting button down or a t-shirt and blazer. Beyond that, a really easy upgrade—as basic as it sounds—is to pay great attention to hygiene. That means clipped nails, neat hair, groomed brows and a good deodorant. (Dates make people nervous, and nerves can make you sweat!)”

Emily Holmes Hahn, LastFirst Matchmaking

 

“One pair of gorgeous dress boots can overhaul a guy’s style without making him feel like he’s not himself.”

Moira, 33, Washington DC

6. The inside always affects the outside.

“Style is as much about psychology as it is aesthetics. Specifically, self-assurance. Confidence is always conveyed when you are wearing something that makes you feel and look like the best version of yourself. But it’s different for everyone, and the trick is knowing how to create that magic. Maybe it’s wearing the color you know that brings out your eyes, the jeans that make you look 10 pounds slimmer, the suit that fits you perfectly, the shoes that garner compliments, the haircut that catches second glances, or the coveted watch you bought after saving up. The common thread is that you feel special when you wear these things, and they always serve to bolster rather than undermine your spirit. The subconscious spring in your step and the assured attitude you present can make any day your day.”

Sandra Nygaard, Former Style Director

 

“Just. Do. You. If that means buying fifteen different pairs of dad sneakers… fine, cool, whatever. Own it. I’d nudge you toward a less is more approach, being loyal to the brands that make you feel authentically yourself, and being as comfortable as possible, always and at all times. Also, when in doubt, you can never go wrong with a fire black hoodie from an emerging designer (shameless plug) you discovered on Style Girlfriend.”

Quincy Moore,  Founder and Creative Director, Knowlita

 

“In regards to why I never wear or buy clothes that are made to look old… If you wanna get weird with me for a second, have a thought on this: Your style can and should be a walking museum of your life experiences. Each item you own, you live in, and most of the memories you make will be in the clothes you wear. Each crease and fade, water damage, coffee spill, or beer stain, rip or tear is an abstract expression of your story and the life you lived. The ever-evolving transformation of a nice pair of raw denim, leather jacket, or suede boots all tell a story. Your clothes are a story that is uniquely you, and they’re a story that can never and will never be duplicated.”

Jordan Rosenacker, co-founder Atlas Coffee Club

 

“Wear what makes you feel happy and comfortable. Style is beautiful because it speaks visually to our own personality. I’ve always viewed getting dress as a form of art making, your body is the blank canvas and the clothes are your medium. We make masterpieces everyday when we get dressed. Clothing has sizes but style does not!! Be confident, be yourself.”

Kelvin Davis, Notoriously Dapper

TELL ME:

WHAT’S ONE STYLE GOAL YOU’VE SET FOR 2019?