Casual Trends I’ve Had My Eye On (And Frugal Picks to Try Them Out)

I had a really interesting conversation with a friend the other day. We talked about how tailored, business, formal, or basically any 'suited' style can actually be easier than dressing casually - at least for a guy who wants to put some effort into dressing well anyway. Why's that?

When you put on a suit, or even a blazer with a shirt and tie, you are automatically presented with a set of garments and accessories, and forced to match them appropriately. Every time, you'll have you shirt, slacks and jacket, and then your tie and pocket square. It does take effort, it does take savvy to do it right, but the blueprint is there for you already.

When you dress casually, however, there is a lot more room to maneuver, which actually presents some more complicated issues. On one hand, it's easy to just resort to jeans and a tee - and not be wrong. The right jeans and tee combo can look even better than the most 'sprezzy' tailored fit. However, when you try to go above the basics, that blueprint you had with your tailored clothes, just isn't there. What's your first step? A graphic tee? Some mirrored shades? Stacked bracelets? When do you stop?

Anyway, the point of the issue is, it actually has taken me a lot longer to delve into stylish casual clothing than it did to dive into sharp, preppy tailored pieces. Now that I have the confidence in my style tastes and judgment to do so, I'm enjoying the hell out of it. Hopefully I'll have some interesting looks to share soon. Meanwhile, here are some casual trends I've really been hooked on, as well as picks so you can snag em yourself without breaking the bank:

Lightweight Bombers: Never really were out of style, but they really seem to be all the rage these days. They can sometimes be pretty damn pricey, but at the same time, it’s becoming easier and easier to find affordable options that have some of the same details and styling as high end, luxury goods.

Men's Lightweight Bomber | Old Navy - $45 ($42 at time of posting)

The Lightweight Bomber | Everlane - $68

Chambray Bomber | J.Crew Factory - $118 ($60 at time of posting)

Jogger Pants: Chinos meet streetwear with these cuffed trousers. Maybe hard to pull off in anything close to a tailored or business casual occasion, but they add some edge (without losing the class) to a more casual, off-duty look. And you know what? I could see them with a more relaxed blazer, too.

Twill Jogger Pants | Gap - $50

Jogger Pant in Campus Khaki | American Eagle Outfitters - $40

Regular Cuffed Chinos | ASOS - $47.61

Tailored Fit Jogger Chinos | Publish via Nordstrom - $82

Chore Coats: This classic workwear piece has seen a surge in popularity, probably in large part due to the popularity of visvim and other high end Japanese denim brands that pull from classic Americana styles. Another one that’s often very expensive, Uniqlo is finally offering a pretty stylish and darn affordable piece.

Denim Work Jacket | Pure Blue x Uniqlo - $80

Land’s End also has this one, which I just wish was denim rather than terry: 

French Terry Chore Coat | Land's End Canvas - $128 ($40 at time of posting)

Bold Printed Shirts: Another trend that has admittedly been around for a while now. To be honest, I thought most of the earlier, affordable iterations were just, kinda, poorly designed. Something about them just made it instantly clear that they were not the designer pieces that they were supposed to resemble. These days, however, there are a bunch of budget-friendly brands really doing it right.

Geometric Print Shirt | Frank & Oak - $55 ($25 credit with our referral link) 

Short-Sleeve Popover in Reverse-Printed Floral | J.Crew - $80 ($50 at time of posting)

Clear-frame (or translucent) Sunglasses: I keep seeing these pop up and love them, but the first pair I really drooled over was a crazy expensive pair by Garrett Leight. I’ve since found them on sale a few times, but never in my price range. Searching for cheaper options has largely been a bust, but recently I found a few that I really dig (for the record, I ended up settling on the American Optical pair via eBay, and love them, although the ‘smoke grey’ frames are a bit darker than I’d ideally like).

Clubmaster Sunglasses with Clear Finish | ASOS - $23 ($15 at time of posting)

Safety Glasses | American Optical via eBay (~$35) or Independence ($70)

Black Waxed/Coated Jeans: This is maaaybe the first mark NYC is making on my style - the edgier, kinda rocker look is much bigger here than in Chicago. Also, not working at a law firm any more is giving me the opportunity to explore my casual tastes more, and has me interested in trying moves along these lines. Just avoid anything too shiny, or it’ll look like leather...tooo rock and roll, man. Those H&M numbers might be pushing it, gotta check em out in person.

1969 Slim Fit Jeans (Coated Black Pigment Wash) | Gap - $80

Waxed Jeans | H&M - $50

OK, I'll leave it at that, but this is one where I'd really love to hear your input - both as to the original discussion at the beginning of the article, as well as any casual trends you have your eye on. Share below!

Outfit Post - Saturday at the Dog Park

We finally had an absolutely beautiful weekend here in Chicago, so Christine and I took advantage of the weather and took a long walk to Wiggly Field (yes, that's the official name) with our puggle, M.C. Hammerpants (yes, that's his real name). As we were walking, it dawned on me that I rarely post really casual outfits on here, and most of what you see of me is in my work or more dressed-up weekend duds, so I figured this would be a good chance to feature a really laid back (but still sharp) look:

If you'll recall from my list of summer style goals, I decided recently that I wanted to start wearing chinos more in a casual setting, as opposed to turning to denim every time I'm off duty. I grabbed these Alpha Khakis from Dockers with just that in mind...the bright color is a little bit much for my law firm day-job, but it's a perfect summery punch of color for a weekend look. I love the fit of Dockers Alphas, but they are just a tad long on me. Since I haven't had the chance to hit up the tailor with these, I rolled the cuffs, which added an extra casual vibe to the look and emphasized the bare ankle (one of my favorite parts of summer).

Up top, I picked this striped tee that I got during the last big Bonobos sale for about $10 (similar here). Not only was it a steal, but the blue and white stripes give a nautical vibe that is very on-trend for spring (and summer, and fall, and pretty much all the time except dead winter). I really like it in this combo as an added bit of color that stays neutral and subtle enough to not come off as clownish in combo with the bright pants.

I also said I wanted to step up my summer footwear game, and I'm in the process of doing so with some Jack Purcell's on the way from Mr. Porter. Meanwhile, though, I really can't go wrong with my Sperry Topsider boat shoes. I picked these up last summer and wear them all the damn time and they just keep getting better and better. In fact, I used to be really OCD about keeping my kicks pristine, but after these got covered in mud at Lollapalooza, I kinda accepted their beat-up-ness and since then have really come to love the personality that some hard wear can give a pair of shoes. I'm also rocking a pair of Pact No-Show loafer socks, which I consider a must-have for the summer, and allow me to kick it sockless without worrying about gross, stinky feet and shoes.

Last, as I was stepping out, I realized it wasn't quite as warm as I thought, especially in the shade. Instead of bringing a light jacket, which honestly would have been a bit much and I would have ended up carrying most of the day, I made a smart choice by throwing on this Frank & Oak OCBD. It's one of my favorite pieces from F&O (you all know my love of an OCBD by now), and I wear it all the time, whether it's to work with a knit tie and a blazer, or on the weekends with jeans and some Chukkas. Here, I took it to new territory by kind of using it as an extra-light jacket. While I normally steer clear of the untucked and unbuttoned look, using this as a jacket let me lighten up on the sartorial 'rules' and embrace the laid-back nature of the look (and the gorgeous day).

For accessories, I topped things off with my brown braided leather belt, which has become my favorite thrift-store find. I literally spent about a dollar on it, and I think it's become a signature part of my style (more on that later). The Form*Function*Form watch that Christine gave me last year was the perfect finishing touch, and was a spot-on match for the brown leather of the belt and shoes. I love that this watch straddles the casual and at least semi-business line very comfortably - I'll wear it with jeans and a Tee one day and with a dress shirt and blazer the next. Versatility is key, my friends.

Anyway, ended up really happy with the 'fit, and had a fantastic day - we hung out at the dog park, took a leisurely stroll home through Lincoln Park, stopped in for cocktails and bacon-wrapped dates (and some treats for the pup) at a neighborhood cafe, and just soaked in the summery Chicago vibes.

How do you relax, sartorially? Do you have a go-to casual look, or are there new trends you are trying to work into your rotation? Share in the comments!

Outfit Details:
T-Shirt: Bonobos (similar) (use our referral link for $25 off)
OCBD: Frank & Oak (use our referral link for $25 off)
Chinos: Dockers Alpha Khaki
Shoes: Sperry Topsider (Editors Note: You can grab these on sale right now at Nordstrom for just $60. Great deal, I'm grabbing a pair if I can).
Socks: PACT No-Show Socks
Watch: Form*Function*Form via Huckberry
Glasses: Grant frames by Penn Avenue Eyewear
Belt: Vintage Thrifted, suckas.

Outfit Post - Dressing Up and Dressing Down

My girlfriend and I have been taking advantage of a service called HowAboutWe ever since I bought her a subscription as a Christmas present. I may do a longer post detailing the awesome perks, since we've been loving it so much, but the short story is that they curate events (or for the couples version, which we signed up for, 'dates'), that can include discounted or exclusive activities, hook you up with a reservation, and voila, next thing you know you're in a new brandy distillery in Chicago watching apples being smashed(?) by a man on a bicycle.

Really, it's been a great way to get us out of the house on the weekend when the weather says to just stay on your couch! Not only does it give my girlfriend and I even more quality time to spend with each other, it also has given me lots of opportunities to exercise my wardrobe by freeing me from my weekday business casual without taking me the whole way down to lounge-on-the-couch casual.

For example, we were back at it again this weekend with a quick trip down to NOSH food festival/farmers market, and I ended up rocking a great balance between the sharp style I like to exude and the more rustic, well, farmers-market-friendly options:

To start off, I love to wear a shirt and tie, and blazer when I can. However, going into this, I knew that coming in a pressed white shirt, silk tie, jacket and chinos probably wouldn't only not fit the crowd, but would also end up getting something spilled on it. So instead, I made some conscious choices to dress down my standard 'fit to something that would work great in the circumstances.

First, I went with generally rougher and more casual fabrics. Instead of a poplin or white oxford shirt, I rocked a plaid, heavier cotton (almost flannel) shirt. For the tie, I went with cotton knit instead of a shinier silk knit, and for the blazer I left my more constructed and sleek options at home, instead grabbing an unlined, soft-shouldered wool twill.

I even made the same general effect with my shoes...these boots are pretty sharp, definitely no shit-kickers, but the suede leather, as opposed to polished, takes things farther into casual territory, as do the lugged soles, which also came in handy walking home through the slushy mess that spring is bringing us.

On the other hand, a few details kept me feeling like I was still on the top of my game. The shirt, for example, while full of more casual details, is actually one of my custom shirts, so the fit is perfect (which will instantly have you feeling like you look 100%). I kept the tie clip, partly because I didn't want my tie falling in my food, and again, because it keeps a sharper edge to the whole look. Last, while I did pick jeans (like a farmer, eh?), I kept them slim and dark to keep some sharp lines from top to bottom. I also decided to go ahead and rock a pocket square (always a bit of a dandy move), but even kept that on the more casual end of the spectrum by picking a cotton, 'bandana' square in a spring-appropriate green that would compliment but not match the green tones in my shirt.

Last, I maintained the balance by throwing a casual waxed cotton jacket on top. No sense in building that careful balance, only to cover it all with a more formal overcoat. Lucky me, the olive color of my jacket worked great with the blues, greens, and greys making up the outfit so far.

Outfit Details:
Blazer - Frank and Oak
Plaid Shirt - Custom by Modern Tailor
Cotton Knit Tie - J.Crew
Cotton Pocket Square - J.Crew
Dark Blue Jeans - Levi's 513
Suede Boots - Polo Ralph Lauren
Waxed Jacket - Frank and Oak

How to Rock It (featuring Past the Pocket)

Last month, Past the Pocket was kind enough to send us one of their fabulous pocket squares for a review. This month, we're bringing their square back to the blog as we feature it in two different outfits. Hopefully these styling examples will give you some inspiration for rocking a similar square yourself. If you like what you see, pick up the 'Some Kind of Blue' chambray pocket square from Past the Pocket for the everyday low cost of $10.

In last month's review, I expressed my opinion that "the best thing about a solid chambray pocket square is it's versatility." With that spirit in mind, I wanted to show you just how versatile this square is by working it into both an all-decked-out ensemble and a laid-back-casual 'fit, side by side.

Admittedly, some chambrays are inherently more rough and rugged, but that's what I love about this fabric from Past the Pocket. It's just soft and luxurious enough that it doesn't look out of place when worn next to sleeker, dressier fabrics like the white twill shirt and blue wool suit.

I picked the wool tie to give this a more seasonal feel (photographed on a beautiful fall day) and to accompany the heartier textural element that the square brings to the look. Also, the sky-blue pin stripes really add to the blue theme of the look. The suit is actually my new made-to-measure number from Dragon Inside (further review to come), and the shirt is another new purchase from Modern Tailor (always highly recommended, use this link for $20 off your first purchase). I'd feel comfortable wearing this to a business meeting, a posh dinner date, or even a wedding.

Not headed to a business meeting, posh dinner date, or a wedding? Dressing for casual Friday in the office, or a trip to that new craft beer bar? No problemo. The square is just as easy to dress down. I picked a simpler fold and tucked it into the pocket of my brown blazer from Frank and Oak.

This blazer can be dressed up as well, but the flecked coloring does lend well to a more casual feel. To keep it dressed-down, I skipped the tie and wore this dirt-cheap Target OCBD, which as actually become one of my wardrobe favorites (despite some previously-mention issues with the armholes). The stripes play well with the color of the pocket square, while the fabric choice helps nudge the square towards casual territory. Not shown in the picture, I rocked this with a simple blue-jeans and boat shoes combo, which is my go-to casual gear. Piece of cake.

How would you wear it? Share your thoughts in the comments, or shoot me an e-mail!

Warm Fall Days

So many seasonal posts coming out of Wide Eyes, Tight Wallets! That's because these in-between times, where it's part fall and part summer, give you the most room to play when it comes to selecting your daily wear. Take my outfit the other day, for example. Friday felt like fall, but was still pretty warm in Chicago (definitely not time to start layering). Plus, it's September, one of those weird months where it might be freezing one day and sweltering the next. Rather than pick one or the other, I decided to dress a bit for both seasons:

First, I held onto some of the summer trends with this short sleeve chambray shirt (from American Eagle, believe it or not). The short sleeve, lightweight chambray was one of my go-to's this summer, and the dot print pattern just adds a bit more summery playfulness to the look.

Moving down, I started to head into fall territory. I wrote a post the other week about wanting a pair of burgundy chino's, but lucky me, I already have a pair of burgundy cords that I picked up at Gap last year. The color is fantastic for these transitional purposes. It let's you move into the darker, more earthy colors of fall while keeping a toe in the pool of all the bright colors that summer has to offer.

I tend to think of corduroy as a good transitional cloth as well, mostly because of the range the fabric offers. Wale refers to the thickness of the ridges on a piece of corduroy. Thin or fine wale can be seen as more formal, and is usually lighter in weight and one of the few corduror fabrics you will want to wear in the summer. Sometimes, you get an effect close to seersucker. Thick or heavy wale fabrics will be more rugged, casual, and warm, and are usually reserved for the winter. This pair is right in the middle, so I get a bit of the rustic fall look without sweating my cajones off.

I finished it off with my Clark's chukkas. I haven't worn these all summer...some people can do boots in the summer, but I am not one of those people. But I love wearing boots. So, now that it's cooling down, this was one of the first 'seasonal' items I unpacked and they finally got their first wear of the fall.

In the end, I think it's a great outfit for the day. It's moved on from summer, not clinging desperately to those last few rays of hot summer sun, but it's not quite ready to embrace the dreary cold days to come, instead walking the line between seasons. When those cold days do come, just throw on a light jacket and the look is just as sharp.

How do you dress on these not-quite-summer but not-quite-fall days?

Dressing Down A Dapper Look

I love to read the comments sections on all the menswear blogs out there. One of the issues I read coming up most often is that guys like the style they are being shown, but feel too overdressed when trying to apply it themselves. For all of you out there feeling the same way, here are a few pointers on how to dress down a dapper outfit:

1. Change Shoes: Simply switching from a pair of well polished oxfords to some slip on loafers, boat shoes, or subtle sneaks can take an outfit from boardroom to barroom in a snap. While your at it, ditch the belt as well. Try something braided or stitched, or perhaps some suede, but this is a great chance to give the plain leather a break. 

2. Let Loose: When dressing sharply, there tend to be a lot of things held very neatly in place. If you want to loosen up your 'vibe,' do the same with your clothes. Lose the tie clip, for one. Heck, don't even bother tucking the tail into the loop on the front blade. Roll up your sleeves. Roll up the cuffs on your pants. Undo a button on your shirt. Loosen your tie a bit. All of these help make you look like you feel more relaxed.

3. Tone Down: This pertains to the materials you're wearing. Swap out your slick white herringbone shirt for a white OCBD, or a semi-spread collar chambray shirt. Pick out a knit tie with a loose weave instead of the shiny silk repp you wear to work. Wear pebble grain or suede shoes instead of high-shine dress leather. Instead of a blazer or sport coat, opt for a classy bomber jacket or an overshirt.

4. Mix and Match: The key here is in avoiding looking like you spent a lot of time laying out the perfect outfit the night before (even if you did). Separate your suit components. Keep the shirt and tie, but throw on a pair of jeans instead of dress trousers. Wear a casual shirt (chambray, flannel, band-collar, pop-over) under your blazer instead of your french cuffs. 

The point is, you can dress well without looking stuffy. I turn to these methods pretty much every casual Friday. While I love the lack of restrictions that a 'jeans day' in the office provides, I still want to look good. Following the advice laid out above, I can end up in an outfit such as this:

Besides the jeans and the boat shoes, every single aspect of this outfit is something that could fit into my office's Monday-Thursday business casual dress code. Now I feel sharp and put together, but won't draw attention in the office as being that guy who dresses up when everyone else is dressing down. Even better, I'm ready to head straight to the bar when 5:00 hits. Because that's what I do.

Easy Transitions

I've written before that my personal style, when I have full freedom to express it, rides the line between casual and formal. My lifestyle doesn't call for a whole lot of formal attire, but I like to dress up the casual pieces I wear in order to stand out and put my best foot forwards. This usually means something like jeans with a shirt and tie, patterned dress shirts instead of plain white or blue, or desert boots and chinos matched with a sport coat and tie.

Another reason I love to wear this kind of style, is that when you are balancing that line, it's easy to tip it in one direction or the other with just a few small changes. For example, yesterday I had a full day of work at the law firm, followed by the quickest of trips home before heading to a Deer Tick concert back downtown.

A few things to note: For those of you who don't know (but I'm sure most of you can imagine), the dress code at the law firm is definitely not casual. The specific firm I work for is much less strict than most, but jeans are not an option, collared shirts are required, and I personally wear a tie every day. Now, also for those of you who don't know, Deer Tick concerts can get just a wee bit rowdy. And I fucking love Deer Tick, so I'm not going to sit on the sidelines and quietly nod my head while John McCauley and co rock out onstage.

Therefore, yesterday's progression of events required some quick wardrobe changes. Here, the KEY word is 'quick.' Check out the before and after pictures, to see just how quick I was able to move from office to rock concert:

Here is the original office attire:

The transition really only took a few changes. First, I ditched the blazer, especially as I anticipated it to get a little warm in the crowded venue.

Before (Work Attire)

After (Concert Attire)

I did decide to stick with the tie. The concert was at a weirdly nice venue, considering how rough-edged Deer Tick can be, so I wanted to keep a little bit of class. I did lose the tie clip though, and unbuttoned my top button for a little looser of a look.

Next, I switched out the shiny black Allen Edmonds for my Clark's, which are much more durable and not quite as stiff (even though I think my AE's are pretty damn comfortable themselves). Most importantly, I won't care if (I mean WHEN) someone steps on my shoes.

Before (Work Attire)

After (Concert Attire)

Along with this, I also swapped the black dress belt for a more casual brown one that I've had for forever.

Before (Work Attire)

After (Concert Attire)

The final product was rock-ready, but still sharp (even if I look a bit dweebish in this picture...):

The great thing is, I could have taken this even farther without having to do much more. Swap out the grey chinos for a pair of jeans; rock a slim tee instead of the button-up; go tie-less, but keep the jacket. It really lets me judge the occasion and dress accordingly without having to stress out about having another entire outfit laundered, ironed, and ready to throw on in the 15 minutes I have at home. The changes are all minor, it's in no way a new outfit, but it's specifically adapted to the situation at hand.

WIWT - 3/15/13

When given the freedom to dress without a dress code, my style of choice is a dressed up casual. Monday through Thursday my work requires strict business casual (no jeans), but even on casual Friday I like to keep myself looking sharp. Today I really wanted to rock these new Tod’s loafers I picked up on eBay about a week ago for a cool $50.

I’ve been looking for this exact shoe for weeks and finally found it - I wanted a slender brown penny loafer with a long vamp (the ‘tongue’ part of the shoe) as a short vamp looks slipper-ish and outdated. There are countless brown loafers on eBay, but most of them are pretty out of style with low vamps and either too round or too square of toes, or they are a different variation on the loafer (tassels or horsebits), which I am just generally less confident about wearing. Anyway, I was overjoyed when I saw these, which were exactly what I was looking for.

When they arrived, I was a little disappointed at first, not due to quality or condition, but because they fit just a little loose. I was hoping to be able to wear these sockless as it warms up, and these are just a tad too big to comfortably do so. My immediate reaction was to decide to re-sell them on eBay and hopefully turn a profit, but just today I slipped them on with a pair of thicker socks and they fit and looked great, so I’m holding onto them as a winter shoe and will look for something else to solve my warm-weather needs.

Along with the aforementioned socks ($15, thick cotton socks from J. Crew), I picked a pair of great Hurley jeans I snagged from Nordstrom Rack for a paltry $20. These jeans are dark enough to look dressy while still meeting the ‘casual’ requirement of a casual Friday outfit. The shirt and tie combo not only dresses things back up a bit, but also let me throw in a little kick of green since we had a small St. Patrick’s day party at work today and I wanted to look the part (more on dressing for St. Patrick’s day here).

In the final details, the tie bar hints at formality while the belt remains dressed-down, once again comfortably straddling the lines of formality.

To wrap it up, this whole outfit is about balancing casual and dressy in a way that works well together. I started dressy with loafers over sneakers, then brought it to the casual side with jeans instead of slacks. Shirt and tie ups the formality, while the wider, well-worn belt anchors the look with another touch of casual. Like I said, if I was given the choice, this is about what my daily wear would look like.

How do you define your style? In a world without dress code expectations, would you be dressing differently on a day-to-day basis?