A couple of a days ago, I e-mailed you asking you send me your current pressing style questions.

I whittled down the couple dozen questions I got and answered them in this post.

If you’d like to send me a question in the future, you can do that by joining my mailing list. The next time I ask for style questions, you can reply to the e-mail.

Ok, let’s get to it.

Gym Style

Nike-Training-Pro-Hyperrecovery-CRobshaw_original

Primoz asks:

“What are some wardrobe pieces that you’d recommend to look good in the gym? Are there any rules that should be “broken” in the gym? (e.g. Is gym a place where you want to keep wearing neutral colors?)”

I’m sometimes surprised by how often I get questions about gym style.

Some say you shouldn’t care what you look like at the gym.

But does it require any extra effort or money to buy cooler looking gym clothes? Not really.

It might even help you mentally.

Based on a very scientific study I conducted on myself, I know whenever I’m wearing some slick, badass looking workout clothes, I feel badass.

And when I look and feel badass, I want to perform badass and crush my workouts.

When it comes to essential gym gear, I would chose:

The wicking t-shirt is a no brainer.

But why do I like shorts and tight combo instead of something like sweats?

Shorts and tights are more versatile as you can ditch the tights in the summer and wear the shorts.

Sweats, on the other hand, might be too hot on warm days.

I also don’t find excess fabric in sweats to be annoying sometimes during certain exercises. I like the movement I get in tights.

The reason for the shorts? To cover up your junk, of course.

When it comes to following “rules”, athletic gear is a place where a lot of style rules fly out the window.

You can wear crazy colors like neon and graphic prints and look great.

When it comes to my personal style in the gym, I like looking “military/tactical”. I usually stick to colors like black and army green, with the occasional pops of colors coming from shoes and accessories.

Nike is my brand of choice when it comes to gym clothes that look cool and function well.

In my experience, their Dri-fit material is the best wicking fabric on the market. Check out their Nike Lab line if you want something even more unique and cooler looking than your standard gym gear.

How can I identify good quality leather from pictures?

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Ed asks:

“I want to buy a leather jacket on eBay. The sellers never seem to answer my question on whether the jacket is either genuine, top grain, or full grain leather. What’s the best way to tell by looking at the listing?”

I would say it’s pretty impossible to identify the quality of leather by looking at it.

I would recommend going to a store, finding something you like and checking out the quality. Then jump back online and look for the jacket at a better price.

My second recommendation is to search for brands that you know use good leather, like Schott.

If you need tips on how spot good leather in person, check out my essential guide on leather jackets here.

What the hell do I wear with black jeans?

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Josh asks:

“Hey Peter,

What do I wear with black jeans? [What are some] good shoes options?”

Treat black jeans like dark blue jeans. Because it’s a neutral color, it can work with almost anything.

Take a look at the examples above. Each one of these looks would work fine with a pair of dark blue jeans.

(Google tip: If you ever have a question how to wear a particular piece, searching “[Name of item] + Ryan Gosling” will usually yield great results. E.g. “Black jeans Ryan Gosling”)

The “No brown shoes with black pants” rule is pretty much obsolete now.

For starters, you really can’t beat a good boot. My current favorites are these from Thursday Boot Company (Both brown and black will work).

Jeans for guys with bigger butts and thighs

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Robert Asks:

“[I have] big legs and butt, where do I find jeans? I had a pair custom made but it was such a hassle.”

Levi’s 541 Athletic fit jeans. You’re welcome.

 

A bag that doesn’t make me look like I’m still in college

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Martin Asks:

“When I was going to [college], I usually just crammed my stuff into a rucksack and that was good enough. Now that I’m in a professional environment, I’m looking for a ‘grown-up’ way to carry around my office stuff. What are my options?”

I’m a big fan of the new wave of briefcase + backpack combos, like the one above from Eastpak. It’s minimal and has a professional grown up vibe. You can wear it as a backpack in transit, then carry it like a briefcase when you’re around the office.

For something a little less techy and more traditional, Filson makes a great one with leather trim.

Advice on getting my first custom suit

fitting

Keane Asks:

“[I’m] getting married in November. I decided to spend my hard earned money on a custom suit.

The guy I’m in contact with did a custom suit for a friends wedding and [we] liked how the groom looked.

I told him that I’d like a grey, charcoal suit that I can wear beyond my wedding day for other special occasions.

I never had a custom suit and I’m excited for something that will fit me immaculately.

Am I doing the right thing? Are there important questions I should be asking?”

I think a custom charcoal grey suit is a very smart move, especially if you’re looking to use the suit beyond the wedding.

I recommending going through Articles of Style’s fit guides and making sure your suit hits all the points.

Here’s the ones you should read:

That should cover what to look out for in terms of fit.

My only personal recommendation is to ask for a “no pant break” in your pants.

It’s clean, classic, and hard to fuck up.

I’ve seen a lot of sites recommending guys to experiment with their pant breaks.

In my experience, most guys do pant leg breaks wrong and just end up looking bad and sloppy. That’s why I usually recommend for my clients to go with a no break.

Also, one quick note: a properly tailored pant won’t require a belt to wear. I’m not a fan of wearing belts with suits.

 

How can I learn how to put together outfits?

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Zubair Asks:

“I’m totally dependent on others to think of outfit ideas. I struggle with visualizing the “end outfit” when buying clothes or looking at my closet.

Is this something that will come to me with time, or will I forever depend on others for ideas?”

Creating outfits is nothing more than combining different ideas from outfits together.

Here’s what I’m thinking when I put together an outfit:

In the photo above, I like the brown shoes Ryan pairs with his grey jeans.

So, I’ll file it away in my head as “brown boots, grey jeans look good together.”

Then, when I’m putting together a new outfit, I’ll think:

“I like wearing my chambray shirt with my grey jeans. My bomber jacket looks good over my chambray shirt. I now know grey jeans and brown boots look good, so I’m going to put all those together.”

Boom.

Now I have a “new” outfit.

Sometimes, it won’t work out. But most of the time, you’ll come out with a great outfit.

My recommendation is that when you see an outfit you like, identify one combination that makes it work (for you). Then file that away to use later in a different outfit.

Think of it like cooking.

Imagine a recipe calls for olive oil and lemon dressing for a kale salad.

You make it and think, “Oh, olive oil and lemon go really well together. I’m going to use this dressing for my avocado salad.”

 

Mixing and matching colors

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Addie Asks:

“I am still blur about colour matching, so I hope you can help me out.”

No problem! I’ve written about how I approach mixing colors here: The easiest way to mix and match color for men.

Dressing for warmer, tropical weather

PHOTO VIA MR. PORTER / TOMMY TON
PHOTO VIA MR. PORTER / TOMMY TON

Gabriel Asks:

“This is my first time sending an email to you. I read all your blogs and emails.

I come from a tropical country (Malaysia to be particular – yes, you have readers from all the way here!) and things like the Ultimate Fall or Winter Guide to Fashion is not exactly applicable to us. I was wondering, besides the typical jeans, shirt, and sneakers, is there something fashionable that a guy like me can wear when going out – on a date, to the movies, etc?”

Thanks for reading and sending me a message!

I got you covered. Check out my essential summer guide.

There’s a lot of great stuff in there for your situation, including some outfit ideas that would definitely work on a date.

What are your thoughts on loafers

alden-lhs-loafers

Kats asks:

“I’d like to hear your thoughts on loafers in general, and any suggestions if you were to choose an “essential” loafer. “

Hey Kats,

In general, loafers lean a bit more on the casual side. More casual than your oxford, more formal than white sneakers.

You could wear them in any place you could wear a minimal white sneaker or oxfords, from shorts, to chinos, to jeans, and suits. But if your workplace is old school Wall St suit and tie situation, it might be a bit too casual. In that case, I would say just go with classic oxfords.

For brand/model recommendations, you can’t beat the classic Alden LHS.

Not too narrow, especially for flat footed guys like me. I’d go for a black or burgundy.

 

Are cargo shorts ever ok?

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Rob asks:

“I’ll be heading back home to Honolulu, where it’s shorts weather year-round. It made me wonder: When will it be deemed acceptable by the fashion world to wear cargo shorts again?

I understand why the big, baggy shorts with huge stuffed cargo pockets that we all wore back in 2001 are not in style.

But what’s wrong with a pair of tailored, well-fitting shorts with slim side pockets?

The modern man carries a minimum of three things with him: phone, keys, and wallet.

This alone justifies cargo shorts in my opinion. I never use back pockets (apart from a ticket or something else tiny) because I don’t want to sit on my stuff. Add in a sunglass case, a pair of earphones, a battery pack, a pen, a lighter, a pocket knife, a flask, etc. and more pockets get handy quickly.

Having numerous pockets also means less chance of any one pocket getting overly stuffed.

I know, I know: just carry a bag. I usually do, in fact. But sometimes it’s nice not to, particularly if it’s too hot for long pants, and I just don’t understand all the hate directed at cargo shorts.”

I feel like this is a chicken and an egg problem. Do you need cargo shorts to hold all your stuff, or are you carrying around all this stuff because you have cargo shorts pockets?

I think the biggest question is do you need to carry around all that stuff to begin with?

I can only imagine cargo pockets swinging around from the weight of carrying a phone, backup batteries, pocket knives, and a flask.

And while having your cargos tailored might improve the fit and look, I suspect it will also accentuate the bulkiness of the stuffed pockets.

So, my suggestion: Be honest with yourself, do you need a flask or sunglass case in beautiful Hawaii?

Is grabbing a beer at a beach bar and hanging your sunglasses nonchalantly in your shirt pocket a better, more stylish option?

Comfortable work clothes for an elementary teacher

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John asks:

“I work with elementary children so I am moving around constantly throughout the day. I sit cross-legged on rugs, and [often] squatting or on my knees.

I’ve always been interested in work uniforms for specific jobs, especially pieces that are cool and functional. (For example: Engineered Garments amazing jackets for Ippudo).

What work-wear would you recommend as an easy, simple and go-to uniform outfit that looks great, but can survive constant movement and wear?”

I would look into getting pants with some stretch in it. It will definitely change your life, especially if you find yourself squatting or sitting on the floor a lot.

Bonobos has a really great pair of stretch chinos that my clients love.

In terms of work inspired clothes that would be great for your situation, I love Engineered Garments’ “Bedford Jacket”, which are very similar to the jackets they made for Ippudo. (photo above)

It’s a style they bring back every season, and you can find it made in casual light weight cottons to more formal, heftier wool.

I particularly love the patch pockets on the Bedford jacket. It’s my preferred pocket style when it comes to blazers because of how easy they are to use.

Combine those with a pair of brown boots and a chambray shirt, and you’ll be the most stylish elementary school teacher of all time.

peter@theessentialman.com'
Author

Hi, I'm Peter. I spent 11 years as a menswear designer here in NYC. Now, I help some of the most successful men look really good as a Private Personal Stylist and writer of The Essential Man. You can learn more about what I do by clicking here