For $50 You Can Buy …
It’s been a while since I did one of these entries, so I thought I’d make up for it by building an entire ensemble for fall, head-to-toe, out of things you can buy for under $50. 
Shirt: Ralph Lauren Rugby has this "antique striped shirt" on sale for $49.99. I’m not crazy about Rugby’s designs when they have a bunch of collegiate stripes and emblems, but this one is simple enough. It also looks like it could go quite well with most casual ensembles. 
Pants: Sierra Trading Post has a bunch of Bill’s Khakis in a variety of colors and fabrics, and this vintage twill in olive would make for a nice fall chino. They cost $79.95 right now, but if you sign up for their DealFlyer newsletter, you’ll get their “special coupon” notices. Lately, they’ve been giving 35% off any one item, which brings these down to about $52 (hey, I’m just $2 off, cut me some slack). Depending on how skinny your legs are, these may need some tapering, however, so you should account for that cost. 
Belt: Narragansett Leathers makes handsome, custom-made belts for under $50. They have a variety of styles, but I like their plain 1.25” belts the most. If you want something more unique, they also have double ring and hoof pick belts for about the same price.
Shoes: It’s hard finding shoes for under $50! Obviously, if you’re willing to pay $100+, and look on eBay, then all sorts of decent options are available to you. For under $50, however, I’ll recommend these Land’s End chukkas. I’m not crazy about the stitching on the back quarters of the shoe, but they’re advertised as being full grain leather, and only cost $49.95. 
Wallet: I really like Chester Mox wallets. They’re completely handmade, built from Horween leather, and produced by a family in Los Angeles that has been working with leather for over a decade. Right now they’re running a promotion where they’ll etch your name or initials into the wallet for free (use the code FREEPRSLZ at the end of the Paypal checkout process). They have a bunch of designs for under $50, but this model only costs $35. A customized, handmade wallet for $35 ain’t bad. 
Watch: Big faced Timex, you got two of those. Well, at least that’s how many you can have for $50. Get the Easy Reader model for $20.24 on Overstock.com. If that one sells out, just check out their other Timex options. Many of them can be had for about $25 each.
Socks: You can get a pair of Gold Toe socks for about $3 at Belt Outlet. Read my review of them here. 
Key fob: This is a bit of a superfluous purchase, but the leather is 225 years old, and it was found at the bottom of a sunken ship! For $24, it’s a pretty cool thing to carry around. You can read more about the special leather in this old article I wrote. 
There we have it. Head-to-toe everything you need for fall, and nearly every item costs less than $50. It’s not the most sartorial of looks, but not bad for a budget. 

For $50 You Can Buy …

It’s been a while since I did one of these entries, so I thought I’d make up for it by building an entire ensemble for fall, head-to-toe, out of things you can buy for under $50. 

  • Shirt: Ralph Lauren Rugby has this "antique striped shirt" on sale for $49.99. I’m not crazy about Rugby’s designs when they have a bunch of collegiate stripes and emblems, but this one is simple enough. It also looks like it could go quite well with most casual ensembles.
  • Pants: Sierra Trading Post has a bunch of Bill’s Khakis in a variety of colors and fabrics, and this vintage twill in olive would make for a nice fall chino. They cost $79.95 right now, but if you sign up for their DealFlyer newsletter, you’ll get their “special coupon” notices. Lately, they’ve been giving 35% off any one item, which brings these down to about $52 (hey, I’m just $2 off, cut me some slack). Depending on how skinny your legs are, these may need some tapering, however, so you should account for that cost. 
  • Belt: Narragansett Leathers makes handsome, custom-made belts for under $50. They have a variety of styles, but I like their plain 1.25” belts the most. If you want something more unique, they also have double ring and hoof pick belts for about the same price.
  • Shoes: It’s hard finding shoes for under $50! Obviously, if you’re willing to pay $100+, and look on eBay, then all sorts of decent options are available to you. For under $50, however, I’ll recommend these Land’s End chukkas. I’m not crazy about the stitching on the back quarters of the shoe, but they’re advertised as being full grain leather, and only cost $49.95. 
  • Wallet: I really like Chester Mox wallets. They’re completely handmade, built from Horween leather, and produced by a family in Los Angeles that has been working with leather for over a decade. Right now they’re running a promotion where they’ll etch your name or initials into the wallet for free (use the code FREEPRSLZ at the end of the Paypal checkout process). They have a bunch of designs for under $50, but this model only costs $35. A customized, handmade wallet for $35 ain’t bad.
  • Watch: Big faced Timex, you got two of those. Well, at least that’s how many you can have for $50. Get the Easy Reader model for $20.24 on Overstock.com. If that one sells out, just check out their other Timex options. Many of them can be had for about $25 each.
  • Socks: You can get a pair of Gold Toe socks for about $3 at Belt Outlet. Read my review of them here.
  • Key fob: This is a bit of a superfluous purchase, but the leather is 225 years old, and it was found at the bottom of a sunken ship! For $24, it’s a pretty cool thing to carry around. You can read more about the special leather in this old article I wrote

There we have it. Head-to-toe everything you need for fall, and nearly every item costs less than $50. It’s not the most sartorial of looks, but not bad for a budget.