Suede Chelsea Boots
Chelsea boots have been popular since The Beatles, but Yves Saint Laurent's revival of their slim profile, tight-fit Chelseas have really brought them back into mass-market appeal. Common Projects – famous for their white sneakers that started a footwear revolution – have adopted the style with a suede twist. They make a striking appearance stacked below skinny jeans, but can be worn beneath slim ones, too. The only thing more striking – the price.
Mark McNairy is a big name in footwear, and has his own line of budget shoes marketed towards more frugal audiences. The construction might be slightly less durable than the original boot, but they're still a top-notch shoe. This is my personal recommendation.
UO often collaborates with other brands to produce awesome clothes, but this is 100% by their own brand. It can be hard to find Chelsea boots with as slim a profile as the Common Projects, but these come very close, and at a much more reasonable price.
G by GUESS is the cheaper option against the standard GUESS line, but the construction is still surely present. A tan suede this lightly colored is rare, and seems like a good buy overall.
Black Slim Denim
Black jeans are the single most versatile pair of pants in a man's closet, and ACNE (Ambition to Create Novel Expressions) makes some of the best. Their cuts are quite unique in the denim world, offering fit styles you don't see many other places. The quality is impressive, too. However, dropping this much dough on a single pair of jeans can make a deep hole in your pocket, and that's not always necessary.
American Eagle makes by-far my favorite jeans on the market. Their flex series offers incredible comfort, almost approaching the level of sweatpants. They fit great on a lot of body types, and offer a variety of styles for you to choose from. Their frequent sales mean you'll usually get a fair price, too.
Uniqlo offers some of the cheapest raw, selvedge denim you can buy. Right now, their selvedge is out of stock, but will most likely return soon. In the meantime, this miracle air option is great for the later months of spring; lots of breathability for warmer weather.
Arizona Flex Slim Straight Jeans, $17.59 with “COOL30”
JCPenney has been closing their physical locations, but their online options are stronger than ever. These jeans have a very slight flex, not noticeable in most scenarios, save for when you need it the most. Good quality for the price.
Mock Neck Cardigan
SNS Herning is famous for their thick, detailed knitwear, especially their renowned Stark cardigan. The hip-to-collar mock opening is relatively unique, and the wool quality is incredible. This is a great piece to throw on when you're running out the door, but the price tag might have you running the other way.
WoolOvers has an excellent lineup of full-wool sweaters at amazing prices. They offer something similar to the Stark, and a whole lot more: check them out if you're in the market for a sweater of any kind.
This piece will be relatively low quality, but the price is so low on some sizes ($29), you really don't have anything to lose. Carefully check the sizing; this brand is known for running at least two sizes too small.
Anoraks are basically pullover rain jackets, which you don't see too often. Fjallraven, based in Sweden, focuses mostly on quality outerwear. Their take on the anorak is detail-rich and built to last. But, you don't have to drop a full paycheck if you just like the way it looks.
L.L. Bean has some of the best customer service around, and their quality is world-renowned. Their garments are the type you could pass down for generations. This particular option lacks some of the details present in the Fjallraven coat, but still maintains the overall look.
Less intended for rain, and more meant for style, this jacket is a more comfortable option. The color is perfect for spring, and the zip collar makes it easy to take off once you get indoors.
Light Wash Denim Jacket
A light-wash denim jacket perfectly pairs with many bottoms, from black jeans to corduroys to joggers. They're easy to toss on and they instantly make it look like you tried. A.P.C. makes some incredible denim, and their jacket offerings are fantastic. They're also very expensive.
I personally own this jacket, and I absolutely love it. The denim is soft and comfortable, the details are perfect, and the cut is right along the beltline. This is a great item for a cheap price – and it's even under a name brand.
Cotton:On Rodeo Jacket, $49.95
CO offers some nice denim jackets in 4 different light washes. You can certainly find something you like here.
Gap's denim offerings are quite nice, and this jacket is no different. The details are there, and the inevitable discounts will bring the price lower and lower.
Persol 714 / 649's, famously worn by Steve McQueen – the epitome of “cool” – have a unique profile when it comes to sunglasses. The thick, raised keyhole is a trademark to the style, and the wider lenses can balance out a variety of face types. The price tag is rather high compared to bargain-bin shades, but there are some affordable alternatives out there.
Warby Parker's option rings in at a fraction of the price of the Persols, and has the most similar profile you're likely to find. Plus, you can even get them as prescriptions!
Zara is a fast-fashion brand, bringing about trendy items at a low price tag. This pair is similar to the original Persol's, but some details are lacking; it's rare to find a 100% lookalike of these shades.
Nordstrom Rack has some good options, especially for wider faces. The keyhole is there, but not necessarily raised. These are more inspired by the 649's, not blatant ripoffs.
IWC is a true watchmaking powerhouse, and this particular item is an incredible piece of work. Chronographs were originally intended for maritime or aerospace purposes, allowing the navigator to dead reckon their way across maps before the invention of GPS. The details here are very expensive: a real alligator leather watch strap, 18k gold, and some of the highest quality internal timepieces on the market. This is the kind of watch you'll pass on to future generations, but sadly, it takes a full generation's savings to afford it in the first place.
Seiko is very well respected in the budget watch community. This is a great option with a similar look that will certainly keep you happy.
Timex makes great watches, but not many chronographs; this is a rare offering, and it looks great. You can always switch out the watch strap for something else further down the line.
Although not a name brand, this option looks quite respectable and maintains the original alligator appearance of the original. For this price, you don't have to worry about how long it lasts.