This week, I take a stab at cleaning out the ol’ Style Girlfriend Reader Mailbag. Remember, send me your questions, and I’ll do my best to answer them here as quickly as I can!

Keegan asks:

Hey Style Girlfriend,

How should a guy like myself with a “preppy” style, find good looking clothes in an area where stores with that type of style are minuscule (i.e. dead center of Missouri)? We’re lucky enough to have an American Eagle, Express, and Macy’s, but that doesn’t leave much room for diversifying a wardrobe.

Hi Keegan,

First of all, thank you for giving me a minor heart attack when your name appeared in my inbox, and I thought you were the Keegan who was the first boy I ever kissed and who emailed me after I talked about him on here awhile back because the story popped up on his Google Alerts, and it was ALL KINDS OF AWKWARD. Little shocks like that to the system are good for you, right? Like cold showers and scary movies.

Second, I think it’s great that you’re looking to diversify your wardrobe, and thankfully it’s easier to do so these days than it used to be, thanks to more and more brands offering their wares on e-commerce sites (though of course, some are easier to navigate than others).

You’re already on the right path, seeking out style advice and inspiration on the internet. Start paying attention to the brands that catch your eye in editorials, both on my site and across the web. Men’s style sites like GQ, kempt, Esquire, and more all feature a mix of well-known brands and up-and-comers that you may not have heard of, and that might not be available in your home town. When you notice yourself drawn to the same brand over and over – start there!

As for preppy brands I like that might not be readily available to you in your town, I’d suggest checking out L.L. Bean Signature, Land’s End Canvas, Gant, and jump on some Rugby clothes before the brand shuts down for good. You should be able to up your style game with a mix of those brands, and good finds from the stores you have nearby.

Brandon writes:

Hi Megan,

I am planning my wedding for next spring and want some advice about choosing the clothing for my groomsmen. I want to avoid the traditional tux route. It will be a fairly casual wedding. I was thinking chinos, chukkas, shirt, tie, and blazer. Thoughts? Suggestions for particular pieces? How can I keep this from getting too expensive for my groomsmen? One of our goals for the wedding is to make it as easy and affordable as possible for our friends and family to be a part of the wedding.

Thanks!

Hi Brandon,

Thanks for your message, and congratulations on your impending nuptials!

I think it’s great that you’re keeping your groomsmen’s budgets in mind with your wedding planning. If you want to go more casual, it sounds like you’ve got a great outfit planned. Depending on your own wedding budget, perhaps you could gift the groomsmen the chukka boots? It would be a very practical groomsmen gift (they’d most certainly wear those shoes again!) and you’d be sure that their shoes would match, and be nice and clean, on your wedding day.

If you felt comfortable asking them to spend a bit more money, you could do custom suits from one of the new roving tailor services, like Indochino, 9 Tailors, or Evolution of Style.

These suits are actually really inexpensive considering what you’re getting – i.e., a suit made to perfectly fit your body. What’s more, I really believe that all guys need a nice suit in their closet. Even guys that say they “never” wear suits (what about for weddings in which they’re not a groomsman?! Do they wear overalls?) My own brother is getting married this summer, and he’s splitting the cost of custom suits from Evolution of Style with his groomsmen. Just something to keep in mind if you and your bride-to-be decide you want a more dressed-up look for your side of the wedding party.

Zach wonders:

I have had earring (two hoops in one ear and one in the other) as well as a beard since pretty much 9th grade.  That was six years ago.  I’ve started considering taking out the earrings and going for a clean shave, and since I’ve recently started reading your blog (it’s amazing, by the way) I thought that it couldn’t hurt to ask your opinion.

Personally, I’m not a fan of guys wearing earrings. It’s just not my thing. Facial hair, on the other hand, is more of a case-by-case basis. I like it on some guys, not on others.

Why don’t you try one or the other – either go for the clean shave, or take out the earrings for a week or two? Then, if that change doesn’t feel so crazy, do the other. I think you’d be surprised at what a difference you notice in women’s reactions – just doing something different really attracts our eye! It’s the same reason why, when a guy decides to start dressing up, he starts turning ladies’ heads right away. We’re so conditioned to seeing you the same way every day that making even the slightest change really stops us in our tracks!

And hey, if you hate how you look, you can always put the earrings back in and grow the beard back. No harm no foul 🙂

And finally, Aniruddha asks:

Hey Megan,

Thanks for all the great advise on this blog. This really helps a lot. I started following them and can feel what a huge difference they make.

Recently I was talking to one of my friend regarding formal shoes and boots. We both wanted to buy for ourselves. I suggested Oxfords and Wingtips. However he didn’t liked the idea and mentioned to me that not many youngsters wear these in office, which sadly is true. Do you think he was right. In the office environment, even though it is formal not many people wear good shoes, and it feels quite intimidating that you turn up as a best-man.

Also, on boots…What exactly is difference between desert & chukka. I am planning to buy one for myself (following your tips and going for wardrobe changes). From what I have seen out there they all have bit rounder and big toe box, which I dislike.

Let’s see…to answer both questions as best, starting with the last first (because I’m wild and crazy like that):

With desert/chukka boots, it’s a case of all apples being fruit, but not all fruit is apples. So, all desert boots are chukkas, not all chukkas are desert boots.

Chukka boots can be made in any material, from shell cordovan to canvas to shell cordovan, it’s their form that makes them chukkas – that is, 2- or 3-eyehole ankle-high boot.

Desert boots are a specific subset of chukka boots. They ALWAYS have crepe rubber soles. Most often they’re light suede, but not always.
As for oxford and wingtips and being the best-dressed man at the office, I really like this pair from Dr. Scholl’s that sort of cuts across the fancy/non-fancy continuum:

You can dress them up with nicer slacks, or wear them with cuffed dark-rinse jeans and look great too.

Got a question for me, or maybe a college guy query for Intern Gabi? Dont be shy, ask away!