Affordable Basics
Most people want to dress well, but they don’t care to spend a small fortune or an inordinate amount of time searching for deals. That means no fancy boutiques or thrift stores, just readily available things that can be quickly purchased for not too much money.
Obviously, if you want the best things, you have to spend either time or money. If you just want to look decent without too much fuss, however, here are my recommendations for where you can get affordable basics.
Suits and sport coats: Land’s End Tailored Fits are workable. If you can swing it, Suit Supply is very good for the price. You can read my review of them here. 
Shirts: TM Lewin sells decent dress shirts for $32 in their clearance section or $160 for four in non-clearance. Their “slim fit” fits reasonably well (neither too blousy nor skin tight), and their collar is big enough to hold a necktie well. For oxford cloth button downs, Lands End Canvas’ Heritage line is passable, though the collars are short and skimpy. If you can afford to, get Brooks Brothers instead. They’re better made and designed. Both Land’s End and Brooks will discount things by about 40% at the end of each season.
Trousers: I’ve yet to come across readily available, highly-recommendable, affordable, high-quality trousers. The best I can offer in this area are Land’s End Tailored Fit trousers, but those will need some tailoring, depending on your build. Brooks Brothers Milano trousers are also workable once they go on sale. 
Jeans: Decent pairs can be bought at Levis, Gap (selvedge denim line only), and Uniqlo (“Made in Japan” line is especially nice). All three are holding sales right now. Note that if you want to shop at Uniqlo, you either have to visit their stores in NYC or go through Suddenlee (which you can learn how to do here). 
Rain coats: If you’re on a budget, rain coats are perhaps best bought second hand, but if you don’t want to deal with the hassle, TM Lewin’s mac is fairly nice. 
Shoes: Loake’s 1880 line, Meermin, Charles Tyrwhitt, Markowski, Ed Et Al, Florsheim's Goodyear welted line, and Allen Edmonds are all worth checking out. Slightly imperfect “factory seconds” from Allen Edmonds can be had for a discount at their Shoe Bank store. You can see what models they have in your size by calling them at (262) 785-6666. Nordstrom also discounts Allen Edmonds to $200 or so during their semi-annual sale. 
Ties: Chipp2 sells very respectable grenadine ties for $47.50. You can get whatever else you need at Land’s End. They hold sales fairly often.
Socks: Gold Toes can be had at Costco or Belt Outlet for about $6 a pair. 
Cufflinks: Get these monkey’s fists cufflinks if you don’t need something more formal. Get something from Kent Wang if you do.
Pocket squares: If you can only buy one, pick up a white linen. Kent Wang sells one for $20, Howard Yount for $25, and Sam Hober for $30. 
Belts: You can get a decent belt from Narrangasettet Leather or Austin Jeffers for between $40 and $50.
Wallets: I prefer the slim profile of a card case over a thick bi-fold. Chester Mox makes some nice ones starting at $39 and they’re offering free monogramming right now as part of a Father’s Day promotion. Saddleback also has a very simple and affordable option at $15. 
Watches: Timex on a NATO strap. The watch itself is $25-35 and you can pick up a strap for about $10 on eBay. Or, if you prefer an automatic, try a Seiko - the Seiko 5 can typically be had for about $60, and several other models are under $100.
Finally, don’t forget to set aside a portion of your budget to have things tailored. Things such as suits, sport coats, shirts, and trousers rarely fit perfectly off-the-rack, but if you bring them to a good alterations tailor, you can make them look twice as good and three times as expensive. 
(Photo from Life)

Affordable Basics

Most people want to dress well, but they don’t care to spend a small fortune or an inordinate amount of time searching for deals. That means no fancy boutiques or thrift stores, just readily available things that can be quickly purchased for not too much money.

Obviously, if you want the best things, you have to spend either time or money. If you just want to look decent without too much fuss, however, here are my recommendations for where you can get affordable basics.

  • Suits and sport coats: Land’s End Tailored Fits are workable. If you can swing it, Suit Supply is very good for the price. You can read my review of them here
  • Shirts: TM Lewin sells decent dress shirts for $32 in their clearance section or $160 for four in non-clearance. Their “slim fit” fits reasonably well (neither too blousy nor skin tight), and their collar is big enough to hold a necktie well. For oxford cloth button downs, Lands End Canvas’ Heritage line is passable, though the collars are short and skimpy. If you can afford to, get Brooks Brothers instead. They’re better made and designed. Both Land’s End and Brooks will discount things by about 40% at the end of each season.
  • Trousers: I’ve yet to come across readily available, highly-recommendable, affordable, high-quality trousers. The best I can offer in this area are Land’s End Tailored Fit trousers, but those will need some tailoring, depending on your build. Brooks Brothers Milano trousers are also workable once they go on sale. 
  • Jeans: Decent pairs can be bought at LevisGap (selvedge denim line only), and Uniqlo (“Made in Japan” line is especially nice). All three are holding sales right now. Note that if you want to shop at Uniqlo, you either have to visit their stores in NYC or go through Suddenlee (which you can learn how to do here). 
  • Rain coats: If you’re on a budget, rain coats are perhaps best bought second hand, but if you don’t want to deal with the hassle, TM Lewin’s mac is fairly nice. 
  • Shoes: Loake’s 1880 lineMeermin, Charles Tyrwhitt, Markowski, Ed Et AlFlorsheim's Goodyear welted line, and Allen Edmonds are all worth checking out. Slightly imperfect “factory seconds” from Allen Edmonds can be had for a discount at their Shoe Bank store. You can see what models they have in your size by calling them at (262) 785-6666. Nordstrom also discounts Allen Edmonds to $200 or so during their semi-annual sale
  • Ties: Chipp2 sells very respectable grenadine ties for $47.50. You can get whatever else you need at Land’s End. They hold sales fairly often.
  • Socks: Gold Toes can be had at Costco or Belt Outlet for about $6 a pair. 
  • Cufflinks: Get these monkey’s fists cufflinks if you don’t need something more formal. Get something from Kent Wang if you do.
  • Pocket squares: If you can only buy one, pick up a white linen. Kent Wang sells one for $20, Howard Yount for $25, and Sam Hober for $30. 
  • Belts: You can get a decent belt from Narrangasettet Leather or Austin Jeffers for between $40 and $50.
  • Wallets: I prefer the slim profile of a card case over a thick bi-fold. Chester Mox makes some nice ones starting at $39 and they’re offering free monogramming right now as part of a Father’s Day promotion. Saddleback also has a very simple and affordable option at $15. 
  • Watches: Timex on a NATO strap. The watch itself is $25-35 and you can pick up a strap for about $10 on eBay. Or, if you prefer an automatic, try a Seiko - the Seiko 5 can typically be had for about $60, and several other models are under $100.

Finally, don’t forget to set aside a portion of your budget to have things tailored. Things such as suits, sport coats, shirts, and trousers rarely fit perfectly off-the-rack, but if you bring them to a good alterations tailor, you can make them look twice as good and three times as expensive. 

(Photo from Life)