Today, trying to dig my way out of the massive Style Girlfriend reader mailbag, knocking a few of your questions out in one go. Which is awesome, by the way. I love hearing from you guys! So if you have a question, email me, megan (at) style girlfriend dot com. Just be patient; I’ll get to you as quickly as I can!

James asks:

I’m in a somewhat unique position. I’m blind. I lost my sight a few years ago due to complications of a severe illness. And now, after years of hard work, I’m rejoining the world. I’m returning to college this fall and none of my clothes fit well anymore. So I need to start over.

I’m 33 and I want to dress well, but leaning toward casual. I live in Phoenix (go Sun Devils) so hot weather friendly is very important. I’m also living on disability currently, so cost is an issue. I’ll have around $1000 to spend. Any help would be greatly appreciated.

First of all, congrats on overcoming such a big challenge; I’m so glad to hear you’re doing better and am excited for you to get back to school. I can’t even imagine all the hard work you’ve put in over the last few years. Yours is a great question, and one I hear from guys a lot.

You’ll definitely be able to build a college-appropriate wardrobe with the budget you have. Thankfully you shouldn’t have a need for suits for awhile (college kids – yes, even those in their thirties – can get away with dress shirts and nice slacks for most academic-related occasions), so you can concentrate on a few pairs of go-with-everything pants, and a variety of shirts (ranging from t-shirts to dress shirts).

 

I have been meaning to put together a comprehensive “Here’s what should go in your closet” post, but – well, it’s kind of a big task, and I just haven’t had the time lately. Thankfully, my good friend Barron over at Effortless Gent created a stellar e-book called Graduating Your Style that is a super great resource for any guy looking to start fresh.

Before you toss everything, though, check out this article on cleaning out your closet. There may be some salvageable items if you get them to the right tailor. It’s always worth it put money into tailoring. With a few nips here, a few inches let out from the waist there, you’ll feel like you’re bringing home all-new clothes, without even doing any shopping.

Good luck with your closet overhaul!

Jacob asks:

Hey Girlfriend?
(Not sure how to address this without sounding like a gay character in a bad ’90’s movie)

Anyway, I have a question regarding Madras. I have been fascinated with it for some time now and I finally broke and bought a pair of pants on eBay. I have been hesitant to buy such a loud article of clothing simply because I have no idea how to wear it.

So I suppose my question is this: What are some effective ways to wear the fabled fabric Madras?

P.S. Love the site

It’s cool, I definitely just pictured you saying that with a Z snap, but it’s fine. Personally, I love madras and think it’s well worth trying out to see if it jives with your personal style. I mean, maybe I’d have dipped my toe into the patchwork pool with a pair of shorts to begin with, but you go hard or go home. I respect that.

Pair your madras with a pocket tee (I love the ones from Everlane and J.Crew) to casz it up (I haven’t figured out how to spell that, but like, short for casual? Cacshz? Cahhsh? Anyways…) and beat-up sneakers or loafers. The key is to keep the other elements pretty simple so you don’t look like you’re angling to be an extra in Wedding Crashers 2: Crashing Even More Weddings.

I’ve learned a lot about preppy style done right from An Acute Style. He manages to wear lots of pastels, prints, and yes madras, without looking obnoxious. Take a gander through his gallery archive for some madras inspiration.

Sterling asks:

I work for an entertainment/business litigation law firm in West LA.  We have a business litigation party this Saturday for which the attire is allegedly casual although I plan to dress a little more business than casual.  I was wondering if you might be able to offer some suggestions for a former football player that will help give me a sleek (meaning not big and bulky) look that is casually dressy but still fits well into a base wardrobe.

I’m thinking dark denim (straight leg, good fit) or a thicker khaki colored pair of pants, a light colored shirt – probably long sleeve, maybe a tie and/or coat but not sure.

On a side note, if you’re ever in LA, I’d like to take you out for dinner.

Hmm, that’s an interesting proposition. Maybe I should start trying for a free dinner every time I’m in a reader’s town? I could get used to that…

As for the party, it appears I may have missed the deadline. That said, I’m sure you looked great, and it sounds like what you had in mind was right on. For any other readers dealing with a business party situation, I say you can’t go wrong in business separates – a sport coat and slacks, or jeans if you think it’ll be really informal. This working-but-not-at-work combo will get you out of a suit, while exuding “corner office cool” as you chat up the boss’s wife. A dress shirt (with the collar open, or a little dressier, with a tie) completes the look.

When it comes to work functions, you always want to err on the side of dressier. Actually, that applies to most situations in life. Meeting a girl’s parents’, first day of work, first day of school – looking more polished than everyone (or at the very least, as polished) is always a good thing.

As for those with a football player past like Sterling, remember to go dark on top and lighter on bottom to draw the attention away from a broad chest and shoulders.

Jay asks:

Heading to Vegas next weekend for a bachelor party. What to wear? To the club, to a nice dinner, day gambling, the pool…I know it’s a pretty broad range but your insight would be very much appreciated.

Veggaaasssssss!!!!

Okay, sorry, got that out of my system. So many questions! Let’s start easy and work our way up. The pool? Swim trunks, a t-shirt and those flip flops I ban the rest of the time.

For day gambling, I say you can’t go wrong in a polo or button-down short sleeved shirt, some dark, straight-leg jeans, and closed-toe shoes, maybe a nice penny loafer or driving shoe. I would stay away from sneakers if you want the dealers to pay you any mind and or respect.

Dealers are used to touristy-y looking guys; you should aim for James Bond on vacation.

At night, if you can get close to this look from Liam Hemsworth, you’re doing good. Dark jeans, dark blazer, and a dark t-shirt or dark dress shirt (collar open, natch) – and, okay, probably different shoes. A little shine, a lot of movie star swagger.

Joe says:

I appreciate your blog and the adviceopinionhelp you provide to your readers. The one thing I have found especially helpful and altogether cool is that you have a dialogue with your readers. I can read other peoples comments and receive feedback on things I say both from you and the community. I am an avid reader (and will continue to be) of JesseDerek at Put This On but they do not have the forum that you provide and not that there is anything wrong with it, I just wanted to take this time to say thank you. Keep up the good work.

Okay, so this isn’t rea-a-a-a-l-ly a question, BUT! It provided me the opportunity to say two things.

1) Put This On has been huuuuugely supportive of Style Girlfriend, exposing their ridiculously wonderful audience to my site over and over again. So a big thanks to Jesse, Derek, and the whole PTO crew for the love. If you’ve read anything by the guys at PTO, you know they put tons (and I mean TONS) of thought into what makes it on to the site, so their lack of a community forum is by design, I’m sure. That said, I always hoped Style Girlfriend would have a community to engage with. Which brings me to…

2) Yes! My comments section, r-i-i-i-i-ght? So awesome! My readers are seriously the best. When I step away from my computer for an hour, I come back and guys are helping each other out answering questions that I haven’t had a chance to address yet. It. Is. Awesome. You guys always are such gentlemen, and I appreciate the politeness even when you’re disagreeing with me, or each other. Until that current goes the other way (and I hope it never does!) the comments are here to stay.

So thank you. and glad to have you Joe!

 

Andy asks:

My favorite, ratty UW t-shirt is threadbare; any tips for fall game day attire?

On Wisconsin…

A reader after my own Big Ten-loving heart. But that said, no way! The threadbare-ier (?) the better! Sports clothes are meant to look a little lived in. You buy the clothes at the student bookstore freshman year, and by senior year, they’re perfectly beaten up. As the years go on, you keep wearing it until your own kid wants to steal it from your closet and, hopefully, make them want to attend your own alma mater.

My sister, brother, and I constantly fought over my dad’s old UW Marching band t-shirts. My sister got the one where Bucky’s playing the tuba; I got the tee above, where he’s leading the band. It’s one of my favorite items in my closet and am glad it feels like it’s only one kegstand away from completely falling apart.

If you’re looking to update/upgrade, do it with your accessories. A new hat with an extra-warm polar-fleece lining, or fancy gloves with space for those hand heaters. And the more Under Armour layers you have for when it starts to get really cold, the better.