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$1,000, Let’s buy a new Wardrobe?(r/malefashionadvice)
2 Lands End OCBDs (One white, one Blue ~$40 each (on sale) $80
2 Lands End Gingham or Plaid shirts ~$40 each ~$80
2 Lands End Tailored Fit Chinos (1 in light beige, one in khaki ~$40/each (on sale)) ~$80
1 pair Clarks Desert Boots in Beeswax ~$70
1 Navy Surplus Pea coat ~$40 at a Navy Surplus store
3 crew-neck Sweaters (different colors @ ~$50/each) ~$150
Levis 514s, dark wash or raw ~$50
LL Bean blutcher moc (not as ubiquitous as Sperry’s) ~$70
Bean boots (For winter or snow) ~$90
Timex Easy Reader ~$25
Allen Edmonds Park Ave. (in brown) ~$200
That leaves you $75. Go to Target and buy plain short and long sleeve tee’s from the Merona line and a few pairs of nice Merona socks.
That will be a very simple wardrobe that can be dressed up or down and should cover all of the basics that a 20 year old needs. The next pickups will be a blazer, more shirts, and more sweaters for variety. Remember that fit is everything; if you are slim, get the LE tailored fit, or take them to a tailor.