The Style Mailbag: Favorite Fall Fits, Dressing Down A Suit, And How To Shine Your Shoes

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Welcome back to the PGP Style Mailbag. Thank you to everybody that submitted a question, and if yours didn’t make it in here, I will do my best to get to it for Edition Three. Also, I feel pretty bad that it took me a month to finish this one, so going forward I will try to pump these out in a timelier manner. Got something to ask? Send me an e-mail at barrett@grandex.co or slide in to the DMs. Alright, let’s get in to it.

Hey B,

What is your favorite go-to fall outfit for men and fav fall outfit on women?

Thank you!

-Anna

Hey Anna, I’ve been thinking about this question for quite some time now. It’s a tough one because I can’t decide which direction I want to take my answer. Should I talk about what I generally live in during the fall or what I’m specifically excited for this fall? And for women, where do I start? Should I answer with what I find most attractive, what I think is the best go-to, or what I think is the most on-trend? I guess I’ll try to touch on a little bit of all of that.

Cooler weather to me, above all else, means two words: Leather Weather. I live for leather jackets. There’s a reason celebs swear by them. They’re luxurious, expensive, and make you look like a rock star. They are an instant outfit-elevator. I love them for men and women, and I always look forward to getting to wear mine come fall.

Now let’s talk about go-to fits. For guys, there is nothing more versatile or sharper looking than a cashmere crewneck. You don’t have to spend an arm and a leg either. Check out brands like Grana and Everlane for cashmere under $150. Even J.Crew just dropped a lineup of $100 cashmere sweaters. Worn with jeans, minimal sneakers or a lace-up boot, and a topcoat that hits you above the knee, you’re pretty much ready for anything autumn throws your way. I’m wearing some version of this outfit for a Friday date-night, and then I’m throwing it on again with a hoodie swapped in for the crewneck when I get up to go grab coffee.

For girls, I’m still all-in on knee and thigh-high boots. They’re hot, full stop. Pair them with a sweater dress and I’m giving you the heart-eyes emoji (or maybe even the drool-face one), but I also love them worn with jeans, a slouchy cardigan, and a tucked in tee. OTK boots have been at the top of everybody’s list for at least two fall seasons though, so if you’re ready to move on to the next wave, then it’s all about the sock boot, which also happen to look sexy as hell with the en vogue sweater dresses.

I could go on and on, so I’m going to leave it there.

Sir Fashion,

Respect, appreciate the hard work. Love the podcast advice on TB.
I have an issue with Cole Haan and would look for some advice on maintaining the current dress shoes I have. I bought two pairs of Cole Haan shoes recently: a pair of drivers to causally wear in nice weather with shorts and a polo and a nice pair of dress shoes with laces that were highly touted for comfort (these would be necessary for trade shows to go with suit). The problem is that the loafers I bought were ruined within like five months of casual wear. Probably a little bit to do with the care level I gave them, but I have had other pairs that are in way better condition with just as much wear.
I’ve been more careful with the dress shoes, but the ease of scuff they sustain is mind blowing. You touch a white rock, you get scuff. I have barely worn them regularly. They gave me leather lotion when I first bought them that I have used. My question is, do you have a better brand that sustains less wear and tear than Cole Haan? What do you use for keeping up with loafers, drivers, and dress shoes?

Thanks,

J

Thank you for the kind words J. I don’t think Cole Haans are more susceptible to wear and tear than other comparable brands. Most leather shoes will scuff pretty easily, so it’s up to you to decide just how careful you need to be with certain pairs.

Let’s start with the driving loafers though. Most of these slip-ons were designed in the vain of actual driving shoes, meaning shoes made for the sole (pun-intended) purpose of driving. The soles are constructed of super thin strips of rubber or some ergonomically placed pads and nubs. They weren’t really intended for daily wear, especially if you’re walking around a lot, and they definitely weren’t meant to be dragged through bars or beaten on your aforementioned “white rocks.” Having said that, I acknowledge that the style was adopted by a certain PGP set as a go-to casual shoe. I had several friends in college that would basically go through a pair of the ubiquitous Cole Haan drivers every semester. If you’re attached to the style, but want something more durable, look for a pair with a full sole; the smaller the amount of exposed leather on the bottom of the shoe, the better. Here’s a save, and here’s a splurge, but you should be able to find other options in between those two as well. You could also try an actual penny loafer. That would achieve a similar look, but give you a sturdier shoe.

Okay, now for a quick lesson in leather shoe maintenance. The leather lotion a store gave you is great for conditioning the leather, preventing it from drying it out, and keeping it soft and smooth, but it’s not what you need for buffing out scuffs and scratches. Have you ever walked through an airport and seen a gentleman sitting up in a high chair getting his boots or oxfords polished? Well, shoeshines exist for precisely the issue you’re describing. Quality leather shoes get scraped up easily, and getting them cleaned up is important. Here’s what you need:

Shoe Polish – Kiwi is a popular brand that offers an array of colors. Pick the one that matches your shoes best.

Polish Applicators – This is what you use to put the polish on the shoes.

Shine Brush – This is what you use to blend in the polish and start the buffing process.

Shine Cloths – You can buy these or do what I do and just cut up an old worn out t-shirt in to long, wide strips

Plastic Storage Box – Put all of the above inside this box and stash it under your sink.

Find a little bit of space wherever you live. Set down a towel you don’t care about or, ideally, some newspaper. Get a slightly damp washcloth or paper towel and wipe down your shoes to remove any dirt, dust or grime. Give the shoes a minute to dry. Next, rub the applicator sponge around in the polish until you’ve got a light layer. You don’t want an excess of polish here. Grab one shoe and apply the polish with the applicator in soft, circular motions on the scuffs and around them in the general area. Think about blending in the color. Then, grab your shine brush and start brushing in the polish to the scuffed areas as well as to rest of the shoe. Spreading the polish around the shoe helps ensure the tone of the shoe stays the same. You don’t want one area to suddenly look like a different color than the rest of the shoe. Finally, put the shoe on and grab your old t-shirt strips or your shine cloths. Grab either end of the cloth and start pulling it back and forth on top of shoe. You’re mainly focusing on the toe box and the heel here, but you want to make sure you’re shining the entire shoe. Repeat on the other shoe. This will take some practice but is super easy to get the hang of. If it sounds like too much work, you can always take them to a shoe hospital who will do the same thing for about $20 a pair.

One more suggestion for shoe maintenance: Cedar shoetrees. They maintain the shape of your shoes, keep them dry, and generally help extend their life.

Hey Barrett,

White jeans in Texas during the fall, does it work?

-Shane

Absolutely. Wearing white jeans in the winter is an awesome move. It’s unexpected so when done properly, it’s a great eye-catching look. Two keys here: First, don’t go for box-fresh, optic white. Make sure they’re either a little worn in, or if you’re buying new, go for something in the off-white or ecru range. Second, make sure the rest of your fit is clearly for cold weather. A long sleeve tee doesn’t cut it here. A chunky wool turtleneck and rugged boots does.

Hey Barrett, just wanna say thanks for doing the mailbag and keep up the good work.   I actually have two questions:  1.) What’s the best fit for jeans if I don’t want baggy but I also don’t like too fitted around the ankles?  2.) When it comes to fall/winter, can I get away with my wearing my spring and summer colored button downs with a vest or sweater, or is that a no go?  Thanks again. 

-Jordan

I would wager that the fit you’re looking for is the most readily available! Just look for anything with the “slim” adjective as opposed to the “skinny” one. Almost every denim brand out there makes something with a fitted but not tight top block (the seat and thighs) and a slim but straight leg. In my experience, the leg opening on these is always in between seven and eight inches across creating a 14 to 15 inch hem. If that’s too narrow of an ankle for you, then you are actually looking for something baggy, but the Levi’s 511, the J.Crew 484, the J Brand Kane, the rag & bone Fit 2 or 3, the AG Matchbox, the Nudie Dude Dan, and countless others all fit the mold you’re after.

As for your button downs, I think you’re fine wearing anything subdued pretty much year-round. Blue and white gingham or banker stripes and Tattersall plaids or multi-checks in lighter colors are all fine for fall and winter, especially under a sweater or vest. The things you should shelve until spring are linen, madras, seersucker, and anything else that makes it look like you’re heading to a yacht in Nantucket.

Barrett,

Figured I’d get in early as I imagine you’ll get a lot of questions before the next mailbag. Recently I made an overdue purchase and invested in a decent dark grey suit for an upcoming wedding. I’ll be to the point — do you have any do’s/dont’s/tips for dressing down a suit? 

I’m planning on using it as my main choice for semi-formal meetings with clients, as well as casual weddings that often come up here in Texas. Is it as simple as skip the tie and that’s my best bet, or do you have any tips and options to make it a more versatile look?

First mailbag was really enjoyable, hope you keep doing them. 

-Kyle 

I’d guess that most guys out there only have one or two suits, and unless you’re a lawyer or a hedge fund manager it’s hard to argue that you need more than that. Navy and charcoal/grey are usually the first two suits we go for as well. Suits in these colors are understated, professional, and you can wear them for any occasion including job interviews, galas, charity events, weddings, and funerals.

Your question is a good one. How do you take a serious suit and make it look like you’re ready to have fun? For me, the answer lies in the details. Put simply, if you want to dress it down, don’t show up in something that would be completely appropriate for a job interview. If you stick with dark socks, a patterned or striped silk tie, and a white or light blue shirt, you’ll look fine, but you’ll also look boring. Weddings and parties are your opportunities to play with all the components. Ties with texture made from fabrics like cotton, linen, or wool go a long way. Wear fun socks (or no-show loafer socks!). Grab a tie-bar in a funky color. Wear a lapel flower. Pop in a loud pocket square. Skip solids and stripes and even plaids, and opt for a shirt with a print.

Let me make this clear though: DO NOT DO ALL OF THE ABOVE. Pick one, maybe two of those accessories to experiment with and keep everything else subdued. Piling all of that on makes you look like a dandy and people will snicker behind your back. Remember that fraternity guy in college that would wear Sperrys and a pair of Chubbies and a Vineyard Vines polo and a Patagonia vest and a Reagan Bush ’84 hat and a pair of Costa 580s with a pair of Croakies all at the same time? Yeah, don’t be that guy.

Wearing something standard and just skipping the tie altogether does dress down your suit as well, but that look always feels to me like you just got off work and are headed to happy hour for bourbon. That, or you end up looking like Pitbull.

Hey Barrett,

Big fan of all your writing and your podcasts.

I have come to you seeking fashion advice for an occasion that seems to always be the same look. I’ve got a rehearsal dinner for a buddies wedding, I was hoping you might some advice on some things to wear that would fit the occasion but also stand out a little. It’s in Columbia, Missouri at the end of the October so I imagine it’ll be pretty good fall/early winter weather. Let me know what you’ve got. 

Thanks,

Landry

Landry, first of all, I apologize that it’s taken me this long to finish up Mailbag numero dos. Your rehearsal dinner has already occurred now, and I wasn’t there to help you out. My bad, man. I hope this anecdote makes you feel a little bit better though. I suck at dressing for rehearsal dinners and other events of the ilk. The biggest gap in my wardrobe is semi-formal and business casual. I never pay attention to it because I don’t have to wear that type of thing to work, and I find it boring to shop for. I’m far more concerned with my next denim or sneaker or hoodie purchase and the nice-shirt-and-pants area of my wardrobe has suffered majorly as a result. All of my sport coats seem to be either too wintery or too springy. I have, like, one dress shirt that I actually like, and it was reserved for the wedding the following day. My dressy pant situation is abysmal.

In late December of last year, I was Best Man in a lifelong friend’s wedding. I knew almost everybody at the rehearsal dinner, and I was giving the only wedding toast for which I’d felt the need to write down an outline and notes in preparation. I’d since memorized the speech and I wanted to feel confident up there with the mike, so I threw out the normal slacks-button-down-blazer look and wore what made me comfortable: Black jeans, a dark button down, and a leather jacket. I got away with it, but in preparation for next year’s docket of weddings and rehearsal dinners, I’m planning on ordering some semi-custom shirts from Proper Cloth and finding a blazer that stands out but works for all seasons. I’m thinking something in a true blue or light navy will do the trick.

In general, a rehearsal dinner isn’t the best time and place to peacock, so wearing an appropriate fit for the venue that fits you well and that you feel great in is the best advice I can give. .

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Barrett Dudley

Barrett may never own a house, but you should see his shoe collection. E-mail him with any style questions: barrett@grandex.co

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