Want to raise some eyebrows?  Walk into an Urban Outfitters in a three piece suit.  It’s like a bizzaro version of some dude in roughed up clothes walking into a luxury store, only to be followed around because the sales associates suspect a shoplifter.  Put on a suit, head into an Urban Outfitters, and all of a sudden you’re the man there ready to keep some people down.  Some get all itchy looking.  You’re a Real Housewife, they’re Holden Caulfield.

But Urban Outfitters still carrys some solid goods at real reasonable prices.  Examples follow.  Free shipping kicks in at $50 and returns are free in-store.
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Merrell Wilderness Canyon Boot – $119.99 ($200)

For more than just an urban enviornment

Was under $100 during the Nordstrom after half-yearly-sale sale.  But sizes got short quick.  If you want more substance over style but still have something that’s not too freaky looking, then these are a good pick.  Suggested over here by Mark in the comments.

Ben Sherman Onion Stitched Nylon Quilted Jacket – $79.99 ($149.00)

Bill Raftery approved.

The Ben Sherman brand always has a decent markup on it, but during a sale like this it comes down to more reasonable territory.  A lighter jacket for sure.  Quilted, but with a rounder “onion” stitch.  Corduroy at the collar.  An alternative for those who don’t want a field type of jacket, and don’t want some puffy insulated thing either.

Spiewak A1 Jacket – $49.99 ($189)

Look closely, and it looks like it's symmetrical.

See the red arrow?  There’s a triangle reinforcement detail there if you look closely, just like on the other pocket.  The tan version seems to indicate that being the case too.  Thinkin’ this hasn’t sold because people think it’s got a weird sort of asymmetrical style thing going on.  But it doesn’t.  Field jacket, utility, workman style?  Yes.

Sebago by The Brothers Bray & Co. St. Croix Camp Moccasin – $79.99 ($125)

So what if the boat is in storage?

Upgraded moc from Sebago.  Premium leather uppers.  Black in color with classic corded laces and a contrasting brown sole.  Boatshoes that you can pull off even in winter.  Wear some wool boot socks with em’ around the house.

Rothco Canvas Duffle – $24.99 ($39)

A thing to put things in. And take them places.

No one will ever… ever accuse you of carrying a man purse.  18.25 x 9.75 x 10  If you really want something this plain, might be worthwhile to check your local Army/Navy surplus store.

Sperry Top Sider Flannel Boot – $99.99 ($140)

Flannel boatshoe boot. Lumberjack Admiral at your service.

Not for everybody.  And we’re running short on time to use em’.  They won’t look or feel all that right come May, unless you’re living pretty close to the arctic circle (or, very much in the Southern Hemisphere.)  Hand sewn.

Levi’s Military Jacket – $59.99 ($98)

Sorta jean jacket like. Kinda.

Great brand and a good look.  Speaking of looks, it holds more than a slight resemblance to this one over here.  Description says it has a “tough woven poly shell” and it certainly looks like it could handle more than a windbreaker.

Hawkwings McGill Wingtip Boot – $54.99 ($78)

Better than the cheap price.

Still love mine.  Some wear started showing pretty early at the toes, but… a) I was treating them like crap.  And b) A little bit of Meltonian colored shoe creme fixed them right up.  Also recently featured by GQ in a slideshow.  Not sure if they know how cheap these things are.  Available in the tan leaning cognac leaning orange (more on that next week…) black, and a brown suede for $40 that looks much less rich in person.  Review of the leathers here.

Industrial Rolling Side Table – $99.99 ($169)

$10 shipping? But it has wheels!

Most likely tougher looking online than it actually is.  Costs an extra $10 to ship.  Seems expensive, but furniture seems to be jumping in price these days.  Much better looking than milk crates.  Still too pricey?  More on how to furnish your place for cheap over here.

No word on when this current Urban Outfitters sale ends…

Someone might label you a carpetbagger, but then again you’d have to have had carpet made of Lumberjacks.  (The finest of all carpets in the world no doubt.)

It’s a traditional doctor style, with a reinforced bottom and those over the top buckles.  Even though it’s a “plaid flannel” exterior, it doesn’t seem to be natural.  Polyester and with faux leather polyurethane trim.  But that’s why it’s under $80 (and ships free.)

At 20″ wide it has almost 2,000 cubic inches of space, so it’s not miniscule.  But would you carry it?  Or is it a little too Al Borland meets Grandma Ma’s over-sized purse?

Leave your vote in the comments section below…

Meanwhile, if you want the plaid in a more traditional duffel style, Ralph Lauren’s “Denim & Supply” line has one on sale for just under $100.  About the same space inside, wool/poly/acrylic blend.

A leather racer-style jacket can be a little hard to pull off if you’re stepping out of a Honda Accord.  No it’s not a requirement to have a motorcycle (or say, a roadster) to wear a leather jacket, but a leather racer or moto style can sometimes look a little out of place.  This jacket lets anyone wear that trim shape and style, and it doesn’t even pretend to be leather.

It’s a decently mid to light weight, not too stiff at all, waxed cotton that looks more expensive than $50.  It doesn’t look like it cost you $200, but that doesn’t mean it’s still not good looking.

Real trim through the sides and arms.  Which is good since it comes with standard bomber style elasticized fabric at the cuffs and waist.  The cuffs and waist aren’t too cinched, and with the trim lines on the body, it doesn’t ride up or poof out when you move.  The one drawback is the left arm pocket.  Some might not like it, some might feel a need to put some ball points in the pen slots for the hell of it (not really.)

For some, it’ll be too short through the body.  It hit my longer-than-average torso a little below my belt buckle, so if you have a noticeable belly, forget it.  If you don’t, know that when I crossed my arms (above) it didn’t rise up that much at all.  Pretty fast looking for fifty bucks.

Note:  Free shipping kicks in at $50.  This is $49.99.  Plenty of sub $5 to pick from to avoid the $10 shipping.

Cognac colored shoes and boots can be limiting.  Most guys stay at arms (or legs) length from them because they’re a little tougher to pair up with the stuff you already have in your closet.  True they’ll be easiest to pair with blue, but don’t shy away from grey, black, and cream.  They pack a solid wallop themselves, so keeping the rest of what you have on pretty simple is the way to go.

For more on the boots, see the full in-person review of the Hawkings McGill Wingtip which did pretty well in our wingtip boot search.  These pairings can work just as easily for cognac lace ups with a slight casual feel.
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1. With a dark waxed jacket:  Pants & Sweater by B.R., Waxed Jacket by U.O., Shirt by GAP

Motorcycle or Roadster ready

Brown and black can be hard to mix, but it is possible if they’re different enough in their shades yet their textures work well together.  The waxed cotton jacket is a stupid $40 on sale, and when put together with a black sweater, light blue oxford, then dropped on top of almost white pants, you’re ready to transition from summer to fall.

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2. With wool pants for work:  Pants by L.L. Bean Signature, Shirt by Gap, Tie Bar by Alfani

Impress without a suit.

So you’re stuck in an office but you spend most of your time in your cubicle.  Nobody wears a suit, but you’d still like to dress a notch above what the norm is.  Wear a tie but keep it wool, like the pants.  A striped watch band on a white dial watch makes sure you’re casual enough.  The boots and their color will catch the eyes of your female coworkers.  (Watch by Victorninox, watch band by American Eagle, tie is vintage)

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3. With denim: Jeans by Levis, Blazer by B.R., Shirt by ratio, Watch by Pulsar

Jeans, an easy but still great play.

You can do plenty with a light blue/leaning grey blazer.  It adds just the right amount of contrast without being Miami Vice-ish.  A uniform tattersall underneath gives a little depth, the jeans are your standard dark blue, and the warm brown of the shoes jump out against all of it.

Your take on cognac or lighter tan leather?  Do you even own a pair of shoes in this shade range or is it something you’ll pass on in favor of a standard medium to dark brown?  Leave it all in the comments below…

Like a great Summer Suit, there’s something about a pair of sturdy and versatile wingtip boots in the fall.  Most have character to burn, and they can be dressed up with many of the rough textures and deeper colors we’ll see once the weather turns cooler.  Our search for the best affordable wingtip boots is on, and feel free to send in suggestions via styleip.  Ships free with code FREEFALL  Good on all Urban Outfitters orders.  Expires 3am ET on 8/25/11

Remember the Florsheim Gaffney?  Specifically in chestnut?  Remember how a lot of us were thinking:  “Damn… only if they came without the lug sole.”

These’ll be a fine replacement.

They’re not quite as nice as the Gaffneys, but they’re awfully close.  Especially considering that they’re available through Urban Outfitters, which doesn’t quite have the rep of a distributor of mega-durable goods.

The leather doesn’t feel plasticky in the least.  It’s not buttery soft but it’s not Steve Madden stiff either, and they’re made in India instead of China.  The sole is rubber but smoothed out.  Not even a hint of bulky lugged traction.

The laces are a nice width which grip well and despite the description saying the uppers are “aged leather,” there’s just one noticeable scuff on these out of the box.  Unlike the Gaffneys which had a soft leather lining, these have a synthetic lining.  Not necessarily a bad thing, just not as nice as the Florsheim option.

Does the tan color lean a little orange?  A little.  Oompa Loompa Orange?  Not quite that orange, but they could stand to be more brown.  Or at least come in a brown option.  Or black.  Maybe that’ll happen in the future.  For now, these will look awfully smart with jeans and/or an all blue setup similar to this one.  Ships free w/ the code FREEFALL.

Best Wingtip Boot under $100 – Thanks to the color options, still the Florsheim Gaffney – $96.00 w/ LINK20
Best Dressed Up Wingtip Boot – Italian Made Ciro Lendini Wingtip Boot – $149.00

There’s a lot of gray area between sneakers and dress shoes.  Finding a few pairs of slightly out of the ordinary laceups to go with jeans and chinos is an incredibly easy way to upgrade your look when away from work.

These look like a blend of the Sebago Brattle ($61.20 w/ code ALAUGUST1 through Sierra Trading Post) and the Cole Haan Henry.  But that’s not exactly saying that they look like a blend of Rachel Weisz and Erin Andrews.

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May God have mercy on us all if such a creature were ever to come to be.

Back to the $30 shoes.  They were $70.  Which is already cheap for a shoe.  Haven’t seen em’ in person either.  They look… like they could be either odd in a good way, or odd in a dreadful way.  Might look a lot better after they get beat up.  Maybe take them outside post purchase and throw them up against a brick wall 5 or 10 times.

But would you wear them?  Leave your vote in the comments below.

It looks nice and fitted, the V dips the absolute perfect amount, and believe it or not it’s made in the U.S.A.

Dots get a bad wrap.  Birdseye is a great pattern.  Pin dots are terrific.  And these polka dots are far from the twister sized circles the rent-a-clown wore on his outfit at your 5-year-old niece’s birthday party.

It’s a cotton poly blend but that has to be outweighed by the Made in the U.S.A. label.  That and the poly will help keep it from shrinking up.  Also, cardigans are like sport coats and blazers.  Keep em’ buttoned as much as possible and don’t let those sides fly like the model does on the U.O. website.

But would you wear it?  Or is it… y’know… a little too Father Know’s Best?

Your take goes in the comments below.
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If you’re not too particular about the color and or width of stripes on your tie… then this might be a good bet for you.  But “bet” is the right word.  You really are making nothing short of a wager, although returns are free.

What you’re getting is a completely unique tie, made in Philadelphia from deadstock (never been worn) or surplus (?) fabrics just about anywhere in the world.  It’s an interesting concept and since each one is unique you really won’t know what you’ll get until you open the box.  Yes you can choose from stripes, plaids, or dots, but that’s as far as you can narrow it down.

So they’re asking you to spend some of your hard earned money on something that could be great, something that could be good… or something that could be downright awful.  Sounds to me like the grown up version of buying a pack of baseball cards.

You could get Ozzie Smith.  But on the other hand, you might get Ken Phelps.

So… you in?  Or is this just a terrible idea all together? Remember, there’s always the thrift store.

It’s just your average navy corduroy, patch pocket, grey tweed patched elbows… blazer.

This thing has a lot going on.  Where to start.  Probably the feature that everyone will first notice is the elbow patches.  The lighter grey tweed jumps out.  A lot.  Maybe too much for some who prefer their elbow patches darker than the rest of the jacket.

The cut looks good and trim but the lapels aren’t hipster skinny.  The length looks pretty short, and if it were made by BDG for Urban Outfitters, I’d say skip it.  Those blazers are chopped so short that they’re awkward.  What’s really odd about this blazer is the one, just one button on each sleeve cuff.  Looks like it’s the exact same size as the buttons on the front too.  Weird.  Not a hard fix for you or your tailor if you want to tack a few more on there.

So… would you wear it?  Leave your vote in the comments section below.

Need something that’s less of a risk?  The Boden Everyday unstructured jacket is still on sale for $98.00. (UPDATE: It’s now on sale for $74.  Skip this thing and go with the Boden…)  Boden comes highly recommended, and the jacket looks superb.  Some average sizes are still available too.

That is one lonely looking button.

These are slim.  Levi’s 514 slim.  Maybe even trimmer than that.  So unless your BMI is in the low 20s, you’re probably going to feel a little squeezed.

Partner w/ your cords.

That’s a shame too.  Because the BDG cords from Urban Outfitters give you a tremendous amount of color options with plenty of sizes available online.  If you find these in your local U.O., you probably won’t find that same size selection (the only 32×32 they had at mine was in the deep navy), and you’ll also probably see them marked up to $39.  But being that UrbanOutfitters.com shipping is a pricey $10, it’s a wash in the end.

If you’ve got some muscle and or extra cushioning on your bones, you might want to spring for the $54.50 Gap Straight fit cords (below).  After trying those on shortly after the BDG pair from Urban outfitters, it’s fair to say that while they’re still quite trim, they’re comfortable compared to the BDGs.  Plus their color options are just different enough.

Consider a pair of the medium gray (shark) straight fits with Gap’s new moleskin jacket, a white 1mx, and a black and red knit tie.  You’re mixing fall and winter textures with a summer (the knit) and it should all play well together.  If you want to go full winter, go with a solid navy wool tie.

If you’re serious in picking up both the Gap Straight Fit cords and Molehair blazer, you can get free shipping on your over $100 purchase with the code GAPSHIP100 at checkout.
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