On Personal Style: Guy’s Edition

{By The Anonymous}

Hey guys. InsideOut writes frequently on the finer points of style, fashion, and general attractiveness for females. However, many male readers remain sorely confused as to what they should be wearing. The purpose of this article is not to teach you how to dress well. The purpose of this article is to teach you where to dress well. 

guy's style

Research indicates that achieving true expertise in any field requires an investment of ten thousand hours, on average. Don’t expect to go from All-American Jock to GQ Guru overnight. It won’t happen. There are lots of intermediate stages and I promise you you’ll screw up at lot (for commentary, see here). Don’t let this discourage you.

The journey of developing style – an individual identity grounded in appearance, juxtaposed against fashion, which changes every season based on the latest runway fad – isn’t simply an investment in your outward appearance, it becomes an integral part of your being. References of Cary Grant, Mr. Rogers, James Bond instantly call to mind a singular look, an image, that overshadows every part of their life. That’s the power of personal style.

So. If you want to augment your study of how to dress well, I suggest you consume in equal measure: GQ, Four Pins, Unabashedly Prep, TSBmen, Ivy Style. All are freely available online. Enjoy.

Now to the purpose of this article: where to dress well.

Note at the outset that I write this from a personal preference for a classic ivy prep aesthetic, with slight influences from military and athletic aesthetics. In less vague terms, it means I love chinos, cardigans, Nikes, quarter-zips, and boots. I have attempted to include enough variety in the sources listed below to enable those who tend more towards other looks to still find helpful material. Off the top of my head, athletic, rocker, urban, prep, military are all covered at varying level of depth.

One final note. Understand that style differs from fashion in many ways, but perhaps the most important uniqueness is that very few looks are not ‘stylish’ in the true sense of the word. Style is meant to be an expression of individual identity and character, and if wifebeaters and low hanging jeans with chains is your expression, that’s your style. The presumption in discussions of style, though, is that a well-composed gentleman capable of entering most social circles is the ideal of male style. Perhaps your incarnation of that ideal looks like he walked straight out of the Ivy heyday, maybe he’s the sleek urban Millennial, maybe he’s Adam Levine v2.0 [if you can actually do this, I will worship you forever. maybe.], the point is now how you reach the goal, it’s that the goal is reached. Clear? cool.

Where to Dress Well [In Alphabetical Order]

men's fashion

Banana Republic 

One of Gap’s spinoff projects, Banana Republic caters to the casual professional. Their collections tend to play off of business staples: slacks, chinos, blazers, collared shirts. It’s rare to find the vibrant hues of prep style here, BR’s palette is colorful, but muted. Their products are usually not cut for slim builds, even though they technically carry a slim fit on certain products, so understand that most items will probably need pickups from a tailor if you’re particular about exact fit [this is especially true for blazers and jackets]. I look at BR when searching for dress shirts or sweaters.

Barney’s New York/Barney’s Warehouse

High end clothing retailer, Barney’s stocks select pieces from a variety of designer collections across a range of aesthetics [though most items favor a military or urban look]. Barney’s Warehouse is exactly that, leftovers from Barney’s that are often marked down over 50% [though this is usually from an initial price tag in the hundreds]. If you know a designer, chances are high Barney’s carries their work, A.P.C., Balmain, Band of Outsiders, Burberry, Jimmy Choo, Junya Watanabe, Prada are all present. Given my status as a near-broke student, I have yet to purchase anything from Barney’s or the Warehouse. I periodically peruse their inventory, though, to look for inspirations for outfits or for pieces that I love and can try to find cheaper versions of elsewhere.* I find Barney’s a fantastic source for jeans, shoes, sweaters, outerwear.

Club Monaco

A budget line from the genius mind of Ralph Lauren, Club Monaco strips down the prep of Ralph Lauren’s signature lines for an urban focused product line. CM has recently revamped its chino lineup to include slimmer fits, but has yet to extend that trend to its shirts and sweater, which still have a fuller/slouchier fit, even in slim. CM’s collections are hit and miss, sometimes they have a great lineup and at other times there might be at most one good product in the group. I have also found their shirt collars to be weirdly constructed; not a fan. But it’s relatively inexpensive, and overall produces solid pieces. I look at Club Monaco for chinos and suits.


Express singlehandedly supplied the entirety of my wardrobe during my early adventures into style and fashion. That monopoly has since been broken, but Express’ affordability [and constant sales] combined with a blend of military, urban and rocker aesthetics continues to make it attractive to many. This is the end all be all for graphic tees, if that’s your thing. Express’ palette used to be very bland, consisting mainly of greys, navy, and black, with the vibrant exception being it’s neon colored dress shirts. It has since expanded that color into a great percentage of its products, but still remains very grey oriented overall. I’ve heard that Express’ jeans and chinos fit poorly, though I don’t have experience to corroborate that. Their slim shirts are truly slim, though arm holes can tend to be too large, causing arm movement to be limited. I look to Express for sweaters and suits.


This European budget clothing giant has taken the US by storm, providing a decidedly continental aesthetic, probably best explained as a blend of skinny fits with oversized items, graphic text on tees, and leather outerwear. H&M opened its online shop in the US in May, and the prices can’t be beat anywhere. Granted, with low price comes lower quality and I wouldn’t rely on anything from H&M to keep me warm in a New England winter, but for layering or for warmer weather, some of their pieces fill a need for variety without breaking the bank. I look to H&M for chinos and cardigans.

J Crew

Probably the entity most responsible for the reintroduction of New England style to the masses, J Crew brings a woodland prep aesthetic to every piece in its carefully designed collections. Without entering the outrageously impractical vibrant color world of Polo Ralph Lauren or J Press at their respective primes, J Crew brings back core items like barn jackets, shawl sweaters, madras chinos, balanced against classic oxfords, and loafers/boots [via collaborations with classic American brands Red Wing, Sperry’s, and Alden’s, among others]. Their pieces are moderately expensive, but well made and fitted, and are central to any aspiring preppie’s wardrobe. I look to J Crew for dress shirts, casual shirts, sweaters, chinos, ties.

J Press/J Press York St.

J Press stores are hallowed ground for preppies, as this chain more or less guided the development of ivy prep style from origins to heyday and continue to produce classic menswear. As one might expect from such a storied designer, their pieces are not cheap. J Press caters to an older audience with more classic, mellow prep essentials [chinos, blazers, colored oxfords, etc.] while it’s new secondary line, J Press York St, brings back the go-to-hell attitude often associated with prep style, full of vibrant colors, slimmer fits, and prep icons like cricket sweaters and madras blazers. I look to J Press York St for blazers, sweaters, and shirts.

Mr. Porter

Online English retailer of luxury menswear, Mr. Porter curates select items from various collections around the world and offers them for the buyer’s perusal. The double-edged sword here is that while you don’t have to wade through multiple collections to find specific pieces, you aren’t seeing all available options. In general, though, I find that their selections are satisfactory. Mr. Porter isn’t cheap, though, and prices generally are in the range of Barney’s or Nordstrom. I look to Mr. Porter for jeans, shoes, sweaters, suits, outerwear.


The powerhouse of athletic products has increasingly become more style savvy, likely as a result of NBA legends like James, Wade, Westbrook, and others becoming involved in the fashion world. Their athletic wear blends perfectly into an urban or prep look, adding a facet of youth and activity via the addition of a hoodie, or sweats, without compromising the integrity of the look. Nike shoes also serve as a fresh change up from loafers or Sperry’s, and the brand has upgraded its sneakers and hi tops via collaborations with top fashion designers. Personally, trading in my sperry’s for a pair of hyperdunks with chinos and a button down or slim crew neck tee results in a completely fresh look that’s equal parts stylish and active. I look to Nike for shoes.

Ralph Lauren

No list of menswear would be complete without due respect given to the demigod of menswear, Ralph Lauren. The number of designers who began their careers at Ralph Lauren is beyond count. From a monetary perspective, Polo Ralph Lauren is the only specific line I will concern myself with covering, though his Label lines are impeccable and often worn by the most glamorous members of society to social functions. As the name implies, Polo Ralph Lauren is inspired by the sport of Polo, a preppy sport if there ever was one. Polo matches were/are  social events, where everyone dressed up, packed a picnic lunch, and watched the game. Vibrant colors and basic pieces [the polo shirt, for one] were often seen. The varying colors in Polo’s collections pays homage to this experience, a note that continues through perfectly slim fitting gingham spread collar dress shirts, and varying fits of colored chinos. I look to Ralph Lauren for polos, shawl cardigans, dress shirts, chinos.

Under Armour

UA has established itself as the Nike of base layers, and not without warrant. Its clothing lines, though, have also produced pieces worthy of including in a menswear style source list, notably quarter-zips, hoodies, and sweats that can take a stuffy outfit to weekend/party ready in an instant. Example: Blazer, shirt, tie, chinos, loafers. You probably just came out of an interview or day at work. Replace the blazer with a hoodie, lose the tie, untuck the shirt, replace loafers with nikes and you’re ready for a night on the town. Example 2: cardigan, button down, jeans, boots. Just another day of fall classes. Switch out the jeans for UA sweats, and you’re rocking a chill style that’s about 2384928374 times more comfortable and just as cool.**


The Asian parallel to H&M, Uniqlo started as a discount Japanese clothing retailer, and has exploded into a global chain with a massive flagship store in New York City. Uniqlo provides menswear essentials, nothing fancy but a little bit of everything. Overall, their products are incredibly well priced for their construction [merino sweater for $40? yes please.], and the website is deceivingly washed out on colors, the actual pieces tend to have a rich, full color. I don’t have experience with Uniqlo pants, but their sweaters and shirts claim to be slim fit, but aren’t anywhere close. Unless you’re full-bodied, plan on either a baggy fit or a trip to the tailor to edit any purchases. Neither is necessarily a deal breaker, but it is an inconvenience. I look to Uniqlo for shirts, sweaters, and blazers/jackets.

Designer Sites

Many exclusive designers offer web stores on their sites. My two personal favorites are Gant and Ovadia & Sons, both heavily influenced by New England/English prep and constantly carry beautiful sweaters and cardigans. Their heavy focus on perfect tailoring makes every piece feel custom designed for you, and that’s an amazing feeling. Granted, they’re expensive [especially Ovadia], but in some cases, might be worth the cost. Look to designer sites for any specific items you know you want and can’t find elsewhere. I look to them for cardigans and chinos/cargos.


I discovered this site, and haven’t purchased a tie anywhere else in over three years. Wide and slim ties in innumerable patterns, fabrics, designs and lengths. Also, bowties and socks. No outfit is complete without quality neck and footwear, and at $15/tie, these prices can’t be beat. Go buy a few. or a lot.

There you have it. A [somewhat] comprehensive list of where to start dressing stylishly.

Please again note that this is a marathon, not a sprint, and that you will waste lots of money on clothing you think is cool, but look back several years later and realize was quite repulsive. We’ve all been there. Pace your purchases, and don’t drop large amounts of cash on central wardrobe items until you’ve formed a relatively clear pictures of what your personal look is. Then build out around that central image.

And have fun doing it. Clothes are fun. Looking great in them is even better.***


– Anon

*When purchasing clothing, you do get what you pay for. I am of the opinion that it is preferable to have a smaller wardrobe comprised of expensive, well-curated pieces, than a massive wardrobe full of mediocre stylish items. Quality is the focus, not quantity. That said, dropping a grand on a sweater is probably a bit overboard unless you’re making seven figures. Or you really like the sweater.

** Note that this presumes these sweats are actually the correct size and are worn around your waist, not the bottom of your posterior. Fit is everything.

*** “Be stylish and develop an individual image. This is the first and greatest commandment of menswear. And the second is like it: get thyself to a gym ASAP. Get fit. Not skinny, not big, fit. All success and women hang on these two commandments.” – Menswear version of the ACTUAL two greatest commandments.