Originally Posted by dakine
I have sneakers, 2 pair running shoes and birks, I have been looking to possibly get a pair of Redwing GT's in Cherry. Would this count as a 'dress' boot? I have a pair of Florsheims for dressier events. My current style is pretty bland/oversized clothing. I havent purchased much lately ie. years and when I was younger I would buy stuff so I could grow into it, well turns out I am not going to grow that much more. I am in Toronto so lots of snow, low/med rain and maybe to warm to layer if it is mid july.
Alright much better.
Here's what I would recommend.
Sweaters: A basic you might want to stock up on.
-1 or 2 V-Neck is solid safe colors, dark gray or navy. If you want to branch out a little bit, try green or red. Find whatever brands fit you best, which in your case could range anywhere from GAP to Margiela. Chances are you can find something that will fit you just fine without breaking the bank.
-Optional but a great addition to your wardrobe, invest in a different kind of sweater. Maybe a nice Nom de Guerre chunky knit, or W+H shawl neck or something that's a little bit out there but still safe. Make you stand out just slightly. If you can find a cheaper alternative to the brands I listed then go for that option.
Shoes: Your best investment, this is the area where you should sink most of your money in (unless you get nice outerwear/suits).
-Redwing GT's would be a casual boot. Would you wear them with a suit? Probably not.
-I would say either a dress boot in black, or 1 pair of boots (can be redwings) then one pair of dress shoes. You can rotate both between dressy and non-dressy outfits.
-Paul Smith, John Varvatos, Buttero, NDC all make great shoes/boots that are dressy but still work great in casual settings. If you want "real" dress shoes ask the MC forum, they know more than I do. These are not cheap and very pricey so you might want to see what deals you can get.
Shirts/Tees/Polos: Basic staples, just stock up on a few well fitting affordable ones you can. Start off with 2-4 of each and you will be fine. Same with sweaters, if you can find nice ones at Old Navy or Gap or whatever then stick with that, you should have no problem finding fitted shirts. If not, try JCrew as their shirts often hit discount range. You can afford to skimp on shirts.
-Pick up something to keep you warm. Maybe 2 jackets if the weather requires you to wear one everyday and you might get tired.
-Shades of Griege, Nom de Gurre, Wings + Horns, APC are all brands that pump out nice outerwear and jackets if you're looking to drop cash. If not, you can stop in any H&M/Zara or probably even Nordstroms.
-Specific examples you might want to look into: Peacoats, Topcoats, Puffer Jackets, Duffle Coats, M65's.
-You really only need one pair. I went through my entire senior year on my pair of jeans and I was fine. Maybe go for a more slim straight look? There are tons of entry level brands such as APC, Crate, Naked & Famous.
-Or, if you want, go budget and get Levi's STF
Since you have so little money, hit up the sales racks at the local shops (Barneys, Nordstroms, etc). Hit up the SF affiliates for awesome discounts. Hit up the Buying & Selling forum for GREAT deals. Before you make each purchase think "Do I really need this? Will I really wear this? Will this last me long enough to justify the price?".
Also, go slowly
. Don't blow all your money all at once, look at how each piece fits into or changes your wardrobe rotation. Your tastes may develop, change, and differ over the next few months. Expose yourself to as many different sources as you can and see what you like and don't like.