Men's fashion

in Annapolis

Church Circle in Annapolis
St. John's College in Annapolis
Take  walk in downtown Annapolis

Current Styles in Annapolis

Double vented blazers

Two-button suits and jackets

Unstructured shoulders on suits and jackets

Slim-fit tapered pants legs

Slim-fit tapered shirts

Spread collar shirts

Two and a half or three inch width ties

Wing-tip and cap toe shoes


Out of Style

Unvented suites and jackets

Three-button suits and jackets

Boxy shoulder pads in suits and jackets

Pleated front pants

Wide-leg pants and jeans

Cuffed pants


Overdress Rather Than Underdress

There is no such thing as Casual Friday.

What is Casual Friday? A reward for people whom dressing well is a burden,” says designer Steven Giles. “When we take joy in our clothing, understanding its importance, to dress down is not a reasonable consideration.”

When someone mentions that you’re  “all dressed up,” that’s a compliment. Your reply should not be haughty, but gracious- a simple thank you, because your ready for whatever the day might bring.

No one is saying to wear a tuxedo to the office picnic, but rather to recognize the occasion- drinks after work, a meeting with new clients-and dress to fit it.

” If you’re the best-dressed person at a party, then you’ve done it right,” he says. ” Because at the core of being well dressed is a comfort, an ease of self, a confidence in who you are. You wear the best because you like the best. Anything else is irrelevant.”


A Gentlemen Gets Dressed Up

A gentlemen takes care that he looks his best, and dresses his best, every day since he never knows when he will meet his next major client or the love of his life. He understands that good grooming-like any other aspect of the gentlemanly life- is not a matter of money. He does not have to run up the balances on his credit cards just to keep his shoes neatly shined, his sport coat brushed, and his hair neatly trimmed. Even if his wardrobe is limited, he knows that as it is carefully selected and well cared for, it can take him- and he can take it- to life’s most challenging occasions. He can be confident that as long as his closet contains a few staples, he is ready to dress and head out at a moments notice.


That after all, is part of the ultimate job as a gentlemen. When it comes to getting dressed, it is not a gentlemen’s goal to stand out from the crowd. He is confident that his intelligence, his resourcefulness, his hearty handshake, and his ready smile set him apart from all the others. His clothes, he knows, are merely there to help him along.


At Winston’s Haberdashery, as clothes help to define your style, so to does the furniture you place in your home. Working directly with interior decorators and local real estate agents, we keep the store stocked with outstanding, contemporary and mid century furniture at a fraction of retail prices. Stop in regularly because many times, we will only get in ONE of a particular item. When it goes, so the next item in line comes in, to find a new home.

Winston’s Haberdashery will keep you in style. Contact us today for your own personal consultation at our store in Annapolis, Maryland.