Finding Personal Style: A Guide for Men

Written By Alison Cebulla

Some simple tips for dressing well and finding your personal style. I’ve learned these by helping male friends over the years. This is a super beginner guide with straight men in mind and on the normie side. It’s good to start with the basics and get creative from there.

I love helping people look and feel good. Personal style can be a way to tell a story of who we are. Dressing well and caring about our appearance doesn’t need to be a shallow, vane exercise: it can be about self worth. Personal grooming and styling can be an exercise in self care, self love, and self expression.

I started taking my male friends shopping when I was in high school when I realized that men in the US often did not get the same messaging as women to take pride in their appearance and figure out what looks good on them.

Stylist is my creative dream job! But alas, I have an established career in public health so it will remain a fun hobby.

  1. Esquire The Handbook of Style: A Man's Guide to Looking Good

I gift this book a lot! It has all the personal style basics and holds up over time even though it was published in 2009. It goes over the basics of wardrobe staples, what to wear for which occasions, body types and clothing, shoes, suits, etc. It’s done with entertaining humor and wit!

“Each year, the editors of Esquire produce a special issue of the magazine devoted to men’s style called The Big Black Book, which has been wildly successful. Using the same pragmatic, highly illustrated approach, and laced with Esquire’s trademark humor, Esquire The Handbook of Style brings readers vital information on every aspect of a man’s wardrobe, from suits and shirts, to shoes and neckties, to watches and other accessories. The style-minded reader will find useful advice on suit fabrics and cuts, the right kind of trousers for his build, the essential outerwear to own, how to dress properly for an occasion, how to tie a tie, how to pack for a trip, grooming strategies, and much, much more. A compact and sophisticated accessory in its own right, Esquire The Handbook of Style will be the style bible for the well-dressed man for years to come.”

Buy this book on Amazon→

2. Stitch Fix Subscription Clothing

This is a great way to start finding personal style with minimal effort! You fill out a questionnaire to start and Stitch Fix mails you a box of clothing every month. You decide what to keep/buy and what to send back. It’s great for finding things you would normally have no idea where to buy and it also saves a lot of time—no shopping required. They learn what you like over time and adapt what they ship accordingly.

Additionally, it’s for a lot of ages and styles, which is great. My brother uses it. My dad uses it. Both of these dudes have developed great personal style after the assist from Stitch Fix

StitchFix.com→

3. Huckberry Clothing Website

This website has a great collection of men’s wear and shoes. Consistently just great stuff—classic and timeless lewks.

Go to Huckberry.com→

4. Poshmark Used Clothing App

Once you find the brands you like and know your size (from ordering on Huckberry or Stitchfix, for example), you can search for those brands and sizes on Poshmark, a clothing store app and website for used clothing. Bonus that this is better for the environment! If it arrives and you don’t like it, you can just press one button to list the item for sale and pass it along to the next person to try—which works surprisingly well.

Poshmark.com→

5. Shoes

Personally for myself I like barefoot style shoes which are characterized by having an actual foot shape (wide toebox), zero drop (no heel), and minimalist sole.

This is a great shoe in that style by Vivobarefoot:

Buy Gobi III Suede Men's on Vivobarefoot.com→

But if regular shoes are your jam, as they are for most humans, a great closet staple is an oxford-style walking shoe. These are great M-F work shoes. They look nicer than regular tennis shoes but are just as comfortable. They’re also extremely affordable on Amazon.

Buy these Oxford walking shoes by Vjamam on Amazon→

Adding a Chelsea boot to your outfit is a super easy way to elevate your whole look. Such a staple. Bonus that they’re super easy to put on. I personally hate shoes with laces.

Buy these Chelsea boots by Astorflex on Huckberry→

6. Brands I Like

A lot of times it’s tough to start because we don’t know what we don’t know. If you go in person, there are typically stylists on staff who can help you find the right clothing—just ask for help.

Here’s a list of brands you can start with for basic clothing:

7. Hair

I have 3 hair tips for straight men:

  1. Google “David Beckham ____ (current year)” and just copy him. You’ll never go wrong.

  2. Get a gay male hairdresser. Many a guy-friend has confirmed this tip.

  3. A recent hack I’ve discovered for finding a hip hairstylist is Google “queer hair salon ____ (name of your city)”. This is how I found Blackroom Salon in Boston and have been getting the best haircuts of my life by Gloria Bila. Queer hair salons are more trendy and you don’t have to get the weirdest haircut they offer—you can get a more vanilla version.

Additionally, ask your hairstylist which hair products to buy.

8. Cologne

I don’t have a ton of tips in this area but I think you can’t go wrong googling “woodsy cologne”. I think just try a few and ask women you know what they think. There are so many brands these days! I think I’d suggest going for the smaller indie brands and not designer.

9. Hats

My only tip is please never ever (ever) wear this type of hat if you are under 80 years of age. It’s for old men. I have checked with every woman (I really have) and we do not like these. Wear a baseball cap instead.

If you own one of these “newsies” hats, throw it in the trash. I’m so sorry if you formerly liked these. Take time to process your grief. Schedule therapy.

10. Copy others’ style

It’s good to subscribe to a men’s magazine to copy others’ style.

Alison Cebulla
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