As far as what one “should” buy, my answer really depends on a few things, none of which concern what season is currently in store.

I am a firm believer that if one splurges on clothes, one should first splurge on essentials, items that never go out of style.  These pieces should be your first priority: a wool charcoal single breasted suit, a wool navy single breasted suit, a couple pairs of shirts (either solid white or solid light blue), a couple of ties (solids and stripes only for now), one pair of black leather oxford lace-ups, one pair of brown leather oxford lace-ups, a wool overcoat (either in navy or charcoal), and a dress belt (black and brown reversible; keep the egregiousness of the belt buckle to a minimum).  I am also assuming you have a pair of dark navy jeans, with no fade or ridiculous embellishments on the rear pockets, as well as solid navy or charcoal sweaters.

This is the foundation of a well-dressed man’s wardrobe; the colors I pick –navy and charcoal- are the two most versatile.  Notice I did not pick a black suit.  I don’t know when it became acceptable to wear a black suit during the daytime, but it is not “appropriate.” 

If you don’t yet have all of these items, get them.  If you feel like you know about proper fit, from reading posts on this site, or from reading magazines, or from other respected forums (Ask Andy about Clothes is a classic), feel free to shop around.  If you are less-than-confident, go to a respected department store and trust the TAILOR (not necessarily the salesman).  Listen to what he has to say, and follow his advice.  Note that magazines such as GQ and the like often pick up on trends that are not deemed “traditional” fit.

Now, if you DO already have these items, pick up pieces from what I am arbitrarily deeming the second “tier” of the foundation.  These items include classics such as bomber jackets, wool peacoats, scarves, mackintoshes, trench coats, slacks, blazers, and suits in colors not previously mentioned (keep them wool, for now).

If you also have these second tier foundation items in your closet, you can start to find more novelty, trendy items.  Read through the trends highlighted on this site; there are plenty and not worth listing here.

As for what I’ve bought recently, I’m never one to buy and tell (designer wise), but I will say that the items included a navy oilcloth peacoat, a crewneck gray sweater, a wax cotton jacket in a fantastic dark olive, and a navy windbreaker with a vivid red detail.  I also managed to find a great pair of cords on Gilt, as well as some ties.  I think my next purchase will be a toggle coat.

If you really are insistent on brand names, I would suggest buying items that do not have labels or logos showing.  You pay for brand names for fit, details, texture and quality of construction (well, you should anyway), not so you can show people how much you can spend.  I have a pretty firm “no logos” rule.  I would make exceptions for jeans from Dior Homme (the “slash” is a logo of sorts) and items from Martin Margiela (the 4 thread indentations are a clever subtle logo).

As far as my favorite stores, I really don’t want to be a walking advertisement for a designer, so I make a conscious effort to mix it up.  Here’s a few of my favorites: I like Steven Alan for button downs; H&M for novelty trendy items; Gilt.com for anything; Alexander Olch for ties; and James Perse for t-shirts.  Michael Kors (the designer himself) is known for loving peacoats, and it is reflected in the peacoats he sells.

One last word on style: an item isn’t a good deal just because it is on sale.  It’s a good deal if you would have paid more than the price for that item, regardless of what the price is and regardless of whether it is on sale or not.

Just because it’s raining out doesn’t mean that your need to water down your sense of style.  Simply adjust to the weather by layering and finishing off the look with a sleek umbrella and pair of rainboots.  Layers of clothing will keep you cozy, and the rain gear will keep you dry.  Here’s how to look slick, even when it’s raining out:

1. Start off your look with a simple foundation: a horizontal striped tee and a pair of straight leg jeans.
2.  Layer a cozy cowl neck sweater on top of the horizontal striped tee, letting the sleeved tee peek out from under the sweater.
3. In warmer climates, all you need is a light jacket to finish off this outfit.  In cooler climates, try a warmer coat in a fabric like wool or cashmere.  Or alternatively, with either climate, try a trench-style raincoat. 
4. Complete the look with your rain gear: a pair of over the knee rainboots (a silhouette that’s very in right now) and a clear bubble umbrella.

What would you wear to look slick in the rain?  Share your style with us in the comments!